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SC IENCE & TECHNOLOGY
PeriodicGraphics
With Compound Interest
Periodic Graphics is a collaboration between C&EN and Andy Brunning, chemistry educator and author of
the popular graphics blog Compound Interest. To see more of Brunning’s work, go to compoundchem.com.
C EN.ACS.ORG 41 D EC E M BE R 8, 20 14
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graphics blog Compound Interest. To see more of Brunning’s work, go to compoundchem.com.
C EN.ACS.ORG 41 AP RI L 13, 20 1 5
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CEN.ACS.ORG 30 J ULY 13, 20 1 5

Periodic graphics
A collaboration between C&EN and
More
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Brunning’s work, go to
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To see all of C&EN’s
Andy Brunning, author of the popular Periodic Graphics,
visit cenm.ag/
graphics blog Compound Interest periodicgraphics.
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COLUMN CRYSTALS PLANE CRYSTALS
C1 C2 C3 C4 P1 P2 P3 P4 P5 P6 P7 P8
COMBINATION OF COLUMN & PLANE CRYSTALS AGGREGATION
CP1 CP2 CP3 CP4 CP5 CP6 CP7 CP8 CP9 A1 A2 A3
RIMED SNOW CRYSTALS GERM OF ICE CRYSTALS
SNOWFLAKES
R1 R2 R3 R4
Classifications & shapes G1 G2 G3 G4
Snowflakes can occur in a huge variety of shapes. This chart

IRREGULAR PARTICLES OTHER SOLID PRECIPITATION KEY shows the general and intermediate levels of classification for
these shapes; they can also be divided further into elementary
levels, which are not shown here.
GENERAL INTERMEDIATE ELEMENTARY
Shape
8
CATEGORIES
39
CATEGORIES
121
CATEGORIES
I1 I2 I3 H1 H2 H3 H4 CODE
C1 Needle-type crystal P2 Sector-type crystal P7 Radiating assemblage of plane-type CP4 Crossed plate-type crystal CP9 Seagull-type crystal R2 Densely rimed crystal G3 Polyhedral ice-type crystal H1 Frozen hydrometeor particle
C2 Sheath-type crystal P3 Dendrite-type crystal P8 Asymmetrical plane-type crystal CP5 Irregular combo: column/plane-type A1 Aggregation of column-type crystals R3 Graupel-like snow G4 Polycrystalline-type ice crystal H2 Sleet particle
C3 Column-type crystal P4 Composite plane-type crystal CP1 Column with plane-type crystals CP6 Skeletal-type crystal A2 Aggregation of plane-type crystals R4 Graupel I1 Ice particle H3 Ice particle
C4 Bullet-type crystal P5 Separated & multiple dendrite-type crystal CP2 Combination: bullets & plane-type CP7 Gohei twin-type crystal A3 Aggregation of column & plane-type G1 Column-type ice crystal I2 Rimed snow particle H4 Hailstone
P1 Plate-type crystal P6 Spatial assemblage of plane-type crystal CP3 Plane crystals with column-type CP8 Spearhead-type crystal R1 Rimed crystal G2 Plane-type ice crystal I3 Broken snow particle
© COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM | Twitter: @compoundchem | Facebook: www.facebook.com/compoundchem

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. BY NC ND
PeriodicGraphics
C EN.ACS.ORG 57 AUGUST 17, 2015

THE CHEMISTRY OF CATNIP
Why do cats go crazy for catnip? This graphic takes a look at the chemical compound responsible and how it works.
O
H
O
NEPETALACTONE
70-99% of essential oil
THE EFFECT OF CATNIP

• Member of same plant family as mint.
THE feline response
• Effect on cats known since the 1700s.
• Affects both domestic cats and wild cats, sniffing licking chewing
including lions, tigers and leopards.
• Is also used as a mild sedative and anti-
head shaking chin rubbing
spasmodic agent in humans.
• Can also be used as an insect repellent.
cheek rubbing headover rolling
body rubbing vocalisation
THE CATNIP RESPONSE
O
H
O
1 2 3 4
The compound nepetalactone, After entering the nasal tissue, The brain signals the amygdala, The cat exhibits behaviour similar
one of the volatile compounds the compound binds to protein (responsible for emotional to that seen in response to cat
given off by catnip, enters the receptors, stimulating neurons, responses) and the hypothalamus pheromones. This lasts for about
cat’s nasal tissue. which then signal to the brain. (behaviour responses). 10 minutes.
APPROXIMATE PERCENTAGE OF CATS AFFECTED BY CATNIP
The susceptibility of cats to catnip is gene dependent and
70% hereditary, and as such not all cats will exhibit a response.
Additionally, young kittens aren’t affected until they reach sexual
maturity. The response to catnip lasts for approximately ten minutes. 6-8
WEEKS
AGE UNDER WHICH CATS ARE UNAFFECTED
© COMPOUND INTEREST 2015 - WWW.COMPOUNDCHEM.COM | @COMPOUNDCHEM

C Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence.
Catnip photo Creative Commons licensed (Liz West, http://www.flickr.com/photos/calliope/476705091/in/photostream) BY NC ND
Cats photo Creative Commons licensed (Sergiu Bacioiu, http://www.flickr.com/photos/sergiu_bacioiu/4321311483/in/photostream/)
Chemical Concerns
FIPRONIL AND EGG CONTAMINATION
Cl N WHAT IS FIPRONIL?
H
C
F C C N
C Fipronil is an insecticide commonly used against
F fleas and roaches, which can also be used against
F C C C N
C F ants, cockroaches, ticks, termites, and more. It kills
F C C C C
S insects by disrupting their central nervous system.
H F It is used in various insect-control products for
Cl H
N both agricultural and domestic use.
H O
WHY IS FIPRONIL TURNING UP IN EGGS?
It appears that Fipronil was mixed in with a red

mite treatment, Dega-16, in order to enhance its
effectiveness. Red mites are common pests on
poultry farms. Fipronil is not authorised to be used
around or on food-producing animals. How the
Dega-16 product became contaminated is unclear
and a criminal investigation is underway.
The contaminated eggs originated from Dutch farms. They have since been reported in 15 other countries and Hong Kong.
15
180 FARMS MILLIONS
TEMPORARILY OF EGGS WITHDRAWN
SHUT DOWN
IN THE NETHERLANDS FROM SALE
SHOULD I BE WORRIED ABOUT FIPRONIL?
? Ingestion of large amounts of fipronil can lead

to kidney, liver, and thyroid damage. However,
the amounts present in the contaminated eggs
are much lower, and at these levels it is unlikely
?
to be a risk to public health. In addition to this,
the ongoing investigation has established
that any affected products have already been
withdrawn from sale in the countries affected.
IN SHORT: LOW LEVEL EXPOSURE TO FIPRONIL IS UNLIKELY TO BE A HEALTH RISK. AFFECTED EGGS HAVE BEEN WITHDRAWN FROM SALE.
© Andy Brunning/Compound Interest 2017 - www.compoundchem.com
C Twitter: @compoundchem | Facebook: www.facebook.com/compoundchem
Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence BY NC ND
“THE DOSE MAKES THE POISON”
APPLE SEEDS PE ARS POTATOES COURGET TES
CONTAIN AMYGDALIN CONTAIN FORMALDEHYDE CONTAIN SOLANIN CONTAIN CUCURBITACIN E

~0.6g/kg of seeds ~0.06g/kg ~0.2g/kg Variable
(higher in green potatoes) (higher in bitter courgettes)
ALL OF THE FOOD ITEMS ABOVE CONTAIN NATURAL CHEMICALS THAT ARE
TOXIC TO HUMANS. HOWEVER, THEY ARE USUALLY PRESENT IN VERY SMALL
AMOUNTS, FAR BELOW THE HARMFUL DOSE.
JUST BECAUSE A CHEMICAL IS PRESENT, DOES NOT
MEAN THAT IT IS HARMFUL IN THE AMOUNT PRESENT.
© COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM

C MADE ON BEHALF OF SENSE ABOUT SCIENCE (@SENSEABOUTSCI) WWW.SENSEABOUTSCIENCE.ORG
MISCONCEPTIONS ABOUT CHEMICALS ARE ADDRESSED FURTHER IN THE PUBLIC GUIDE, ‘MAKING SENSE OF CHEMICAL STORIES’, AVAILABLE HERE:
www.senseaboutscience.org/pages/making-sense-of-chemical-stories.html BY NC ND
N AT U R A L & M A N - M A D E C H E M I C A L S
A COMMON MISCONCEPTION IS THAT ALL MAN-MADE CHEMICAL S ARE HARMFUL , AND ALL NATUR AL CHEMICAL S ARE GOOD FOR US.
HOWE VER, MANY NATUR AL CHEMICAL S ARE JUST A S HARMFUL TO HUMAN HE ALTH, IF NOT MORE SO, THAN MAN-MADE CHEMICAL S.
OH
OH
N HO OH
OH
H HO O
O
H
O
HO
NH2
HO
O O
OH
N
OH
H
O
HO
O
ETHYLENE GLYCOL
H
MUSCIMOL H H
FOUND IN FLY AGARIC

HO USED IN ANTI-FREEZE
O O
MUSHROOMS
SOL ANINE O OH
N FOUND IN GREEN
POTATOES A SPIRIN
AT 1 0 0 0 M G / K G
USED AS A PAIN-RELIEVING DRUG
E N
OH O
SE OF O
O
TS BO
O OH C N
FE
D
HO O
S- Na
Y
EF
HO OH
W
E
HO OH NH
IC
EIG
N
D
TOX
O
AMYGDALIN
HT
-MA
SODIUM THIOPENTAL
FOUND IN APPLE SEEDS
AT U R A ALL CHEMICALS CAN BE
FORMERLY USED FOR LETHAL
INJECTIONS
BROADLY DIVIDED INTO
T WO CATEGORIES:
IGHT
NO T
HO
NATURAL OR MAN-MADE
AN
F F
OH
WE
OX
O
C C
L
M
HO
IC
OH
Y
O O F F
D
n
EF
HO
O
E TEFLON (PTFE)
F
B
C F
HO OH
TS O USED IN NON-STICK PANS
OH SE
EN / KG
SUCROSE AT 1 0 0 0MG O NH2 O
ALSO KNOWN AS TABLE
SUGAR OH H
N
O OH
O O O OH
O HO O
HO OH
OH H H
CITRIC ACID PROPYLENE GLYCOL A SPARTAME
WATER ARTIFICIAL SWEETENER
FOUND IN LEMONS & LIMES ESSENTIAL FOR LIFE FOOD ADDITIVE - SOLVENT,
HUMECTANT & THICKENER
“ E VERY THING IS POISON, THERE IS POISON IN E VERY THING . ONLY THE DOSE MAKES A THING NOT A POISON.”
PAR ACEL SUS , 1493 -15 41, ‘ THE FATHER OF TOXICOLOGY ’
A N Y S U B S TA N CE , I F G I V E N I N L A RG E E N O U G H A M O U NT S , C A N C AU S E D E ATH . S O M E A R E LE TH A L
A F TE R O N LY A FE W N A N O G R A M S , W H I L S T OTHERS REQUIRE KILOGRAMS TO ACHIEVE A LETHAL DOSE.
CHEMICAL TOXICITY IS A SLIDING SCALE, NOT BLACK AND WHITE - AND WHETHER A
CHEMICAL IS NATURALLY OCCURING OR MAN-MADE TELLS US NOTHING ABOUT ITS TOXICITY.

C MADE ON BEHALF OF SENSE ABOUT SCIENCE (@SENSEABOUTSCI) WWW.SENSEABOUTSCIENCE.ORG
MISCONCEPTIONS ABOUT CHEMICALS ARE ADDRESSED FURTHER IN THE PUBLIC GUIDE, ‘MAKING SENSE OF CHEMICAL STORIES’, AVAILABLE HERE:
www.senseaboutscience.org/pages/making-sense-of-chemical-stories.html BY NC ND
Undeserved Reputation?
ASPARTAME: ARTIFICIAL SWEETENER
O NH2 O
H
N
O OH
O
ASPARTAME
Aspartame is an artificial sweetener,
commonly used as a sugar substitute.
BREAKDOWN PRODUCTS
Aspartame breaks down into phenylalanine, aspartate,
and methanol in the body. Only around 10% of the
aspartame content is converted into methanol,
and this amount is much less than we ingest from
other sources. Methanol is further metabolised into
formaldehyde and then formate, which is excreted
in the urine. Much larger amounts of methanol than SOFT DRINKS TOMATO JUICE RED WINES
generated by aspartame have been shown to cause no 55 mg per litre 180-218 mg per litre 99-271 mg per litre
formaldehyde or formate build-up in the body, so there
are no associated health concerns with these levels. AVERAGE METHANOL CONTENT
(aspartame is metabolised to methanol in the body)
EFFECT ON BRAIN EFFECT ON HEALTH PHENYLKETONURICS

At normal dietary levels, there is Studies show that people who drink Phenylketonuria affects 1 in 10000
no neurotoxicity from products of beverages that contain aspartame people. Sufferers can’t break down
aspartame metabolism. There is also do not have an increased risk of any phenylalanine, so should not drink
no evidence aspartame can induce cancers. At normal dietary levels, aspartame-containing products,
or enhance susceptibility to seizures. there are no adverse health effects. which must be clearly labelled.
There is no conclusive evidence that ingesting aspartame can cause headaches.

HEADACHES Double-blind studies have found it to be no more effective than a placebo at
producing headaches in those who identified as sensitive to aspartame.
The FDA’s acceptable daily
3750mg 118mg
The amount of aspartame in a 12 ounce can of Diet Pepsi.
intake (ADI) of aspartame In order to exceed the FDA’s average daily intake, you’d need
(assumes 75kg body weight) to drink approximately 32 cans of Diet Pepsi in one day.
IN SHORT: ASPARTAME POSES NO RISKS TO HEALTH AT DIETARY LEVELS, UNLESS YOU SUFFER FROM PHENYLKETONURIA

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STORIES FROM CHEMISTRY HISTORY
SUSAN SOLOMON & THE OZONE HOLE
F
SUSAN SOLOMON O
O
O Cl
C
Cl
Cl
BORN
1956 Solomon’s work confirmed that ozone
could react with chlorofluorocarbons on
the surface of polar stratospheric clouds.
Provided first direct Her work informed the Montreal Protocol,
evidence of chlorine compounds legislation which regulates chemicals that
breaking down ozone damage the ozone layer.
OZO N E A N D C H LO R O F LU O R O C A R B O N S
chlorine
F F radical OVERALL
Cl C Cl UV Cl C Cl O O O
O O
Cl Cl
O O
CFC O
O O O O
Cl O
Cl O O O In the stratosphere, CFCs are
O O
broken down by UV radiation,
ozone releasing highly reactive chlorine
radicals. These react with and
break down ozone molecules. The
O O chlorine radicals are regenerated,
O
Cl O O O Cl so they can go on to react with
O O thousands of ozone molecules.

Ci Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence.
BY NC ND
TODAY IN CHEMISTRY HISTORY
23RD JANUARY – GERTRUDE B. ELION’S BIRTHDAY
GERTRUDE b. ELION
1988
BORN
23 January 1918 Elion was jointly awarded the 1988 Nobel
Prize in Physiology or Medicine for work
DIED on the development of a number of
drugs, based on biochemical differences
21 February 1999 between human and pathogen cells.
S HN NH2
Working both alone and O2N
with George Hitchings, H N OCH3
N S N
Elion discovered new N
drugs against a variety N H2N N OCH3
of diseases. Her name N N N N
N OCH3
appears of 45 different H
patents and she was
awarded 25 honarary
doctorates.
MERCAPTOPURINE AZATHIOPRINE TRIMETHOPRIM
first treatment for leukemia to prevent transplant rejection antibiotic
O O Cl N
OCH3
N O N
NH HO
N
NH N N
N
HO N N NH2
N N O HO OH
H H2N N NH2 NH2
ALLOPURINOL ACICLOVIR PYRIMETHAMINE NELARABINE

treatment for gout antiviral for herpes infections for malaria and toxoplasmosis treatment for cancer

BY NC ND
4TH FEBRUARY – PATENT ISSUED FOR TEFLON (1941)
F F F F
C C C C
F F F F
n
TETRAFLUOROETHENE POLYTETRAFLUOROETHENE
Teflon is the brand name for polytetrafluoroethene (PTFE). It’s a white, waxy substance,
and was actually created by accident by Roy Plunkett in 1938. During research on new
TEFLON PAN refrigerants, the tetrafluoroethene Plunkett was using was accidentally polymerised.
HOW DOES IT WORK? IS TEFLON SAFE?
F F F F F F F
327˚C MELTING POINT
260˚C
C C C C C C C RECOMMENDED MAX
SAFE USE TEMPERATURE
F F F F F F F
During appropriate use, Teflon does not reach the
temperatures required for it to degrade. However, if the
Teflon’s non-stick properties are in part due to the strength coating is overheated the polymer can begin breaking
of its carbon–fluorine bonds, which are chemically inert. down, and the fumes produced can cause flu-like
Additionally, due to the fluorine atoms, the intermolecular symptoms. At present, the long term effects of human
forces between PTFE and other molecules are very weak. exposure to these fumes are still largely unknown.

BY NC ND
16TH FEBRUARY – THE KYOTO PROTOCOL (2005)
192 TARGET
5.2%
COUNTRIES by 2012 relative to
1990
signed and
ratified
ratified but
withdrawn
signed but
not ratified
GREENHOUSE GASES
H
+ –
C O C O O N N HYDROFLUOROCARBONS
H H
H
PERFLUOROCARBONS
SULFUR HEXAFLUORIDE
METHANE CARBON DIOXIDE NITROUS OXIDE
Greenhouse gas emissions
Emissions (million metric tons)
35K
The Kyoto Protocol is an international treaty to reduce the emission 30K
of six greenhouse gases. 192 countries are party to the protocol, but 25K
only 38 had binding targets for the first period (2008–2012). These 38 20K
countries met their target collectively – but an absence of binding 15K

10K
targets for developing nations such as China and India meant that
5K
worldwide greenhouse gas emissions continued to rise.
1990 2012

BY NC ND
28TH FEBRUARY – LINUS PAULING’S BIRTHDAY
LINUS PAULING X X
BORN
Pauling is famed for his work on the
28 February 1901 nature of chemical bonding, for which he
received a Nobel Prize in Chemistry. He
DIED proposed the Pauling electronegativity
scale in 1932. He also carried out research
19 August 1994 on biological molecules.
E LEC T R O N EG AT I V I T Y A N D T H E PAU LI N G S C A LE
δ– δ+ – +
THE PAULING
X X X Y X Z ELECTRONEGATIVITY SCALE
COVALENT POLAR IONIC

BOND COVALENT BOND
0.0–0.4 0.4–1.7 >1.7
DIFFERENCE IN ELECTRONEGATIVITY VALUES
Electronegativity is a measure of the tendency of

an atom to attract electrons when it is part of a
compound. Generally, electronegativity increases
moving towards the top right of the Periodic Table. UNKNOWN 1.25-1.50 2.00-2.50
The difference in electronegativity between two
bonded atoms gives information on the nature of 0.75-1.00 1.50-1.75 2.50-3.00
the chemical bond between them.
1.00-1.25 1.75-2.00 3.00-4.00

BY NC ND
19TH MARCH – SIR NORMAN HAWORTH’S BIRTHDAY
SIR NORMAN HAWORTH HO

OH
1937 O
O OH
BORN OH
19 March 1883 Haworth was a British chemist who

won a Nobel Prize in 1937 for his work
DIED on carbohydrates and vitamin C. He also
developed a way of drawing 3D sugar
19 March 1950 structures that bears his name.
VITAMIN C HAWORTH PROJECTIONS
HO OH CH2OH
OH
O
HO O OH
O HO
O OH OH OH OH
OH OH
OH
GLUCOSE HAWORTH PROJECTION
Haworth discovered the molecular
structure of vitamin C, and also
created its first artificial synthesis. Haworth projections are used to depict the cyclic forms of
He also deduced the structures of a sugars. They are useful because they clearly show which
number of different sugars. groups are above and below the ring.

BY NC ND
19TH APRIL – GLENN SEABORG’S BIRTHDAY (1912)
GLENN SEABORG
1951
BORN
19 April 1912 Seaborg was involved in the discovery
of ten transuranium elements, including
DIED Seaborgium (named after him). He was
a joint winner of the 1951 Nobel Prize in
25 February 1999 Chemistry for his work.
S E A B O R G ’ S E L E M E N T D I S C OV E R I E S
Pu Cm Bk Es Fm No Sg
1940 1950 1960 1970 1980
credited as lead discoverer
Am Cf Md KEY: credited as co-discoverer
As well as discovering elements, Seaborg and his colleagues discovered over 100 isotopes of different
elements in the Periodic Table. He also participated in and contributed to the Manhattan Project, the
U.S. research that helped develop the first nuclear weapons.

BY NC ND
27TH APRIL – WALLACE CAROTHERS’ BIRTHDAY
WALLACE CAROTHERS O
H
N
N
BORN H
O n
27 April 1896
NYLON 6,6
DIED Carothers invented nylon using

condensation polymerisation, and also
29 April 1937 had a hand in the invention of neoprene.
O O MAKING NYLON
H H
+ N B N
C A C H H Nylon is a polyamide, a type of condensation
H O O H polymer. Condensation polymerisation is
when many monomers (smaller molecules)
join together to make a polymer, with a small
DICARBOXYLIC ACID DIAMINE
molecule, often water, being lost. A general
Monomer A Monomer B scheme for making polyamides is shown.
O
HO NH2
OH H2N
O O O
H
HEXANEDIOIC ACID 1,6-DIAMINOHEXANE
C A C N B N + 2 O H
H H
Nylon 6,6 is made using the monomers shown
n above. Carothers’ group first created nylon using
these monomers in 1935.
POLYAMIDE WATER

BY NC ND
30TH APRIL – THE DISCOVERY OF THE ELECTRON (1897)
SIR JOSEPH J THOMSON

1906
BORN
18 December 1856 Thomson discovered the electron,
found the first evidence for isotopes of
DIED stable elements, and won the Nobel
Prize in Physics for ‘investigations on the
30 August 1940 conduction of electricity by gases’.
ELEC TRONS & THE ‘PLUM PUDDING’ MODEL OF THE ATOM
VOLTAGE
CATHODE RAY CATHODE RAY FLUORESCENT

GENERATED DEFLECTED SCREEN
Thomson generated a cathode ray in a tube with a partial vacuum. He showed the rays were deflected by
an electric field. Comparing this with how much they were deflected by a magnetic field, he deduced that
cathode rays were made of negatively charged particles, which he termed ‘corpuscles’. The discovery led
to his ‘plum pudding’ model of the atom, with electrons scattered throughout a cloud of positive charge.

BY NC ND
12TH MAY – DOROTHY HODGKIN’S BIRTHDAY
DOROTHY HODGKIN R
H
N
H
S
1964
CH3
O N CH3
BORN O
OH
O
12 May 1910
Hodgkin used X-ray crystallography to
DIED determine the structure of vitamin B12, for
which she won a Nobel Prize. She went on
to determine the structure of insulin.
29 July 1994
KE Y S T R U C T U R E S D E T E R M I N E D BY H O D G KI N
PENICILLIN (1945) VITAMIN B12 (1955) INSULIN (1969)

H2NOC
CONH2
H2NOC
H H N R N
CONH2
R N S Co+
CH3 H N N
H2NOC
O N CH3 CONH2
N
O O
NH N
HO
OH O O
O O P O
-
O
HO
Hodgkin confirmed the structure of Vitamin B12 was, at the time, the most Hodgkin first grew crystals of insulin
penicillin – the first time the structure complex molecule tackled by X-ray in 1935, but it was another 34 years
of a whole molecule had been crystallography. Its structure took before she determined its three-
calculated using X-ray data. Hodgkin eight years to solve. dimensional structure.

Image: National Portrait Gallery, CC-BY-NC-ND licence. BY NC ND
28TH JUNE – EMIL ERLENMEYER’S BIRTHDAY
EMIL ERLENMEYER R1
OH
R1
O
3
R R3
BORN 2
R2
R H
28 June 1825
The first to isolate several organic
compounds, and invented the Erlenmeyer
DIED (or conical) flask. He was also the first to
suggest double and triple bonds could
22 January 1909 form between carbon atoms.
CYLINDRICAL NECK
Can be stoppered using

OH O
a rubber bung or glass
stopper.
R1 3
R1
CONICAL BODY R 2
R3
Allows contents to be R
swirled without spills. R2 H
FLAT BOTTOM
ENOL FORM KETO FORM
Doesn’t tip over, unlike
round-bottomed flasks.
R groups represent variable portions of the molecule
THE ERLENMEYER FLASK THE ERLENMEYER RULE
Erlenmeyer created the flask that takes his name Erlenmeyer investigated keto-enol tautomerism. His rule states
in the late 1850s. It’s also known as a conical flask that all alcohols with an OH group attached to a double-bonded
and is now a mainstay of the science laboratory. carbon become aldehydes or ketones, as these are more stable.

BY NC ND
16TH JULY – THE TRINITY NUCLEAR BOMB TEST (1945)
T H E T R I N I T Y B O M B : A P LU TO N I U M I M P LO S I O N D E V I C E
PLUTONIUM (6.2 kg) The Trinity nuclear

bomb used a plutonium
core. Explosive charges
VACUUM SPACE surrounding the core
compress it when they are
detonated. This, combined
with neutrons from an
initiator in the centre of the
NEUTRON REFLECTOR
core (consisting of beryllium
and polonium), lead to a
fission chain reaction and
EXPLOSIVE CHARGES nuclear explosion.
T R I N I T I T E F O R M AT I O N
RADIOACTIVITY
The heat of the atomic blast caused Plutonium & Uranium
surrounding sand to melt and solidify from the bomb
into a glassy residue referred to as
trinitite. This glass is usually a pale Isotopes from the fission
process (e.g. Sr-90, Cs-137)
green colour, and mildly radioactive.
The colour isn’t due to the radioactivity, Activation products
but occurs as a result of small amounts (e.g. Co-60, Ba-133, Eu-152)
of iron ions present in the glass.

Image: © Hannes Hiller – used with permission: https://www.facebook.com/microXtals/ BY NC ND
25TH JULY – ROSALIND FRANKLIN’S BIRTHDAY
ROSALIND FRANKLIN
BORN
Rosalind Franklin was a chemist and
25 July 1920 X-ray crystallographer whose work was
instrumental in the discovery of the
DIED structure of DNA. She missed out on a
Nobel Prize for her work as they are not
16 April 1958 awarded posthumously.
P H OTO G R A P H 5 1 A N D T H E S T R U C T U R E O F D N A
BASE BASE BASE
O O O
O O O
P O O P O O P O O
O- O- O-
DNA is a polymer made up from monomers called nucleotides.

A sugar phosphate backbone (above) forms the two strands,
which are held together by hydrogen bonds between the
bases found on these strands (below).
H
H
N O H N
N N H O
Photograph 51 is an X-ray
diffraction image of DNA taken N
N G N H N C
A N H N T
during Franklin’s research. It was N N
crucial in developing a model of N N
N H O
DNA and confirming its double O
H
helical structure.
ADENINE (A) & THYMINE (T) GUANINE (G) & CYTOSINE (C)

BY NC ND
31ST JULY – STEPHANIE KWOLEK’S BIRTHDAY
STEPHANIE KWOLEK H
H
N N
H H
N N
H H
N N
H H
N N
H
O
O O O O O O O Cl
OH
BORN
Stephanie Kwolek created the polymer
31 July 1923 known as Kevlar while working for the
chemicals company DuPont. She also
DIED developed the ‘nylon rope trick’ classroom
demonstration, which produces nylon in a
18 June 2014 beaker at room temperature.
KE V L A R ’ S C H E M I C A L S T R U C T U R E A N D U S E S
OH
H
N
H O
N
H
n
Kevlar is a polymer, a long molecule formed from the reaction of many smaller molecules known as monomers. Kevlar is used
in body armour and bulletproof vests due to its high tensile strength. It is also used in fighter plane panels and wings, petrol
tanks for Formula 1 cars, cut-resistant gloves, car and bicycle tyres, some ping pong bats, and some mobile phone casings. In
1995 Kwolek received DuPont’s Lavoisier medal for her research, and is still the only woman to have received this award.

BY NC ND
7TH AUGUST – GERMAIN HESS’S BIRTHDAY
GERMAIN HENRI HESS ∆Hθr = ∆Hθf (products) − ∆Hθf (reactants)
BORN Germain Hess was born in Switzerland,

but his family moved to Russia early
7 August 1802 in his life, and his chemistry work took
place there. He is known for ‘Hess’s
Law’, published in 1840, which relates to
DIED enthalpy changes of reactions and allows
calculation of unknown enthalpy changes.
30 November 1850
H E S S ’ S L AW A N D E N T H A LPY C H A N G E S
RO U TE 1
Hess’s law states that the enthalpy
change of a chemical reaction (∆H,
∆Hr the heat evolved or absorbed) is
independent of the path taken by
A B the reaction. In other words, even if
it is possible for a reaction to take
place via multiple routes, the overall
enthalpy change will be the same.
∆H1 R O U TE 2 ∆H2
Hess’s law is useful because we
can’t always measure the enthalpy
INTERMEDIATE PRODUCTS change of a reaction directly.
However, known enthalpies of
formation (∆Hf, the enthalpy
change when a chemical substance
∆Hreaction = ∆H1 + ∆H2 is formed from its component
elements) can be used to calculate
The enthalpy change for the reaction (∆Hr ) is equal to the sum of the enthalpy the unknown enthalpy change of
changes for the alternative route for the reaction (∆H1 and ∆H2 ). the reaction.

BY NC ND
30TH AUGUST – ERNEST RUTHERFORD’S BIRTHDAY
ERNEST RUTHERFORD
BORN α β +
30 August 1871
Awarded the Nobel Prize in Chemistry for
work on radioactivity, and named alpha
DIED and beta radiation. Also developed the
Rutherford model of the atom from his
19 October 1937 famous gold foil experiment.
Small no. of particles

GOLD FOIL EXPERIMENT show large deflection DETECTING SCREEN
1/8000
In this famous experiment,
α
+ GOLD FOIL
carried out by Hans Geiger and
Ernest Marsden between 1908
and 1913, alpha particles were +
fired at thin metal foils. Most
Most particles show
of the alpha particles passed + little or no deflection
straight through the foil, but a
small number were deflected 7999/8000
back at a large angle. VACUUM
This experiment showed that, contrary to previous models, positive charges (protons) are not spread evenly
throughout the atom, but are concentrated in a small, dense centre: the nucleus. A cloud of negative charges
(electrons) surround this nucleus. Alpha particles that collided with the nucleus were repelled.

BY NC ND
6TH SEPTEMBER – JOHN DALTON’S BIRTHDAY
JOHN DALTON
BORN
Dalton took pioneering steps in
6 September 1766 developing atomic theory, and also
made a series of symbols for atoms and
DIED molecules. He also carried out research
into colour-blindness (from which he
27 July 1844 himself suffered).
DA LTO N ’ S 3 6 C H E M I C A L S Y M B O L S (C R E AT E D I N 18 0 3)
G P S
OXYGEN HYDROGEN NITROGEN CARBON SULFUR PHOSPHORUS GOLD PLATINUM SILVER
C I N T L Z B An
MERCURY COPPER IRON NICKEL TIN LEAD ZINC BISMUTH ANTIMONY
Ar Ma U Tu Tit Ce
ARSENIC CALCIUM MANGANESE URANIUM TUNGSTEN TITANIUM CERIUM POTASSIUM SODIUM
CALCIUM MAGNESIUM BARIUM STRONTIUM ALUMINIUM SILICON YTTRIUM BERYLLIUM ZIRCONIUM

BY NC ND
7 TH NOVEMBER – MARIE CURIE’S BIRTHDAY
Marie Skłodowska Curie NOBEL PRIZE x 2

BORN PHYSICS CHEMISTRY
7 November 1867 1903 1911

DIED First woman to win a Nobel prize; first
(and only) woman to win twice; only
4 July 1934 person to win twice in multiple sciences.
84
92 Po
U 88
Ra
The term ‘radioactivity’, Curie noticed uranium ores Her work led to the
used to describe the were more radioactive than discovery of polonium
atomic decay process that pure uranium. She suspected (named after her native
produces radiation, was other, more radioactive Poland) and Radium (from
coined by Marie Curie. elements were also present. the Latin for ‘ray’).
Curie died from aplastic anaemia at the age of 66, likely due to long-term radiation exposure,
the health risks of which were not known at the time of her research. As well as the elements she
discovered, there is also an element in the periodic table named after her: curium.

Photo: CC-BY licence; source: https://www.flickr.com/photos/tekniskamuseet/12835367815 BY NC ND
PERIODIC TABLE: ELEMENT NAME ORIGINS
1 2
Symbol Key Language of Origin Name Source
H He
Table Colour Key

Hydrogen GREEK ANGLO-SAXON HELIUM
Atomic number Element symbol MINERAL
Water-forming Sun
LATIN SPANISH ASTRONOMICAL BODY
1
3
Li
4
Be H
Hydrogen
RUSSIAN
ENGLISH
NORSE
ARABIC
MYTHOLOGY
5
B
6
C
7
N
8
O
9
F
10
Ne
LITHIUM BERYLLIUM BORON CARBON NITROGEN OXYGEN FLUORINE NEON
Water-forming
PERSON
Stone Berylios GERMAN GAELIC Buraq/borax Charcoal Nitre-forming Acid-forming To flow New
Language SWEDISH NONE – FROM NAME PLACE

11 12 Element name Origin/meaning of origin 13 14 15 16 17 18
NaSODIUM
Mg
MAGNESIUM
JAPANESE PROPERTIES
Al
ALUMINIUM
Si
SILICON
P
PHOSPHORUS
S
SULFUR
Cl
CHLORINE
ArARGON
Soda Magnesia Bitter salt Flint Bringer of light Brimstone Greenish-yellow Idle
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K
POTASSIUM
Ca
CALCIUM
Sc
SCANDIUM
Ti
TITANIUM
V
VANADIUM
Cr
CHROMIUM
Mn MANGANESE
Fe IRON
Co COBALT
Ni NICKEL
Cu COPPER
Zn ZINC
GaGALLIUM
Ge
GERMANIUM
AsARSENIC
Se
SELENIUM
Br
BROMINE
Kr
KRYPTON
Potash Lime Scandinavia Titans Vanadis/Freya Colour Magnet Iren Goblin Devil’s copper From Cyprus Zink France/Gaul Germany Orpiment Moon Stench Hidden
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
RbRUBIDIUM
Sr
STRONTIUM
Y
YTTRIUM
Zr
ZIRCONIUM
Nb NIOBIUM
Mo
MOLYBDENUM
Tc
TECHNETIUM
Ru RUTHENIUM
Rh RHODIUM
Pd
PALLADIUM
Ag Cd CADMIUM
InINDIUM
Sn TIN
Sb
ANTIMONY
Te
TELLURIUM
I
IODINE
XeXENON
SILVER
Dark red Strontian Ytterby Gold-like Niobe Lead Artificial Russia Rose-coloured Pallas Soilfur Calamine Indigo Tin Not alone Earth Violet Stranger
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
CsCAESIUM
Ba
BARIUM
E57-71 Hf
HAFNIUM
Ta
TANTALUM
W
TUNGSTEN
Re
RHENIUM
Os
OSMIUM
Ir
IRIDIUM
Pt
PLATINUM
Au GOLD
Hg MERCURY
Tl
THALLIUM
Pb LEAD
Bi
BISMUTH
Po
POLONIUM
At
ASTATINE
Rn RADON
Sky blue Heavy Copenhagen Tantalus Heavy stone Rhine Smell Iris Little silver Gold Mercury Green twig Lead White mass Poland Unstable Radium
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr
FRANCIUM
Ra
RADIUM E89-103 Rf
RUTHERFORDIUM
Db
DUBNIUM
Sg
SEABORGIUM
Bh BOHRIUM
Hs
HASSIUM
Mt
MEITNERIUM
Ds
DARMSTADTIUM
Rg ROENTGENIUM
Cn COPERNICIUM
Nh NIHONIUM
Fl
FLEROVIUM
Mcmoscovium
Lv
LIVERMORIUM
Ts
TENNESSINE
Og
OGANESSON
France Ray Ernest Rutherford Dubna Glenn Seaborg Niels Bohr Hessen Lise Meitner Darmstadt Wilhem Röntgen Copernicus Japan Georgy Flerov Moscow Livermore Lab Tennessee Yuri Oganessian
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
La
LANTHANIUM
Ce CERIUM
Pr
PRASEODYMIUM
Nd NEODYMIUM
Pm PROMETHIUM
Sm SAMARIUM
Eu
EUROPIUM
Gd GADOLINIUM
TbTERBIUM
Dy
DYSPROSIUM
Ho HOLMIUM
ErERBIUM
Tm THULIUM
Yb
YTTERBIUM
Lu
LUTECIUM
Lie hidden Ceres Green twin New twin Prometheus Samarskite Europe Johan Gadolin Ytterby Hard to obtain Holmia Ytterby Thule Ytterby Paris
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
Ac
ACTINIUM
Th
THORIUM
Pa
PROTACTINIUM
U
URANIUM
Np NEPTUNIUM
Pu
PLUTONIUM
Am CmAMERICIUM CURIUM
Bk
BERKELIUM
Cf
CALIFORNIUM
Es
EINSTEINIUM
Fm FERMIUM
Md
MENDELEVIUM
NoNOBELIUM
Lr
LAWRENCIUM
Ray Thor First ray Uranus Neptune Pluto America Marie Curie Berkeley California Albert Einstein Enrico Fermi Dmitri Mendeleev Alfred Nobel Ernest Lawrence
© Andy Brunning – www.compoundchem.com. Produced in collaboration with Prof Mark Lorch, University of Hull.
Ci CHEMUNICATE Shared under a Creative Commons 4.0 Attribution-NoDerivatives-NonCommercial licence. BY NC ND
Chemical Concerns
FIPRONIL AND EGG CONTAMINATION
Cl N WHAT IS FIPRONIL?
H
C
F C C N
C Fipronil is an insecticide commonly used against
F fleas and roaches, which can also be used against
F C C C N
C F ants, cockroaches, ticks, termites, and more. It kills
F C C C C
S insects by disrupting their central nervous system.
H F It is used in various insect-control products for
Cl H
N both agricultural and domestic use.
H O
WHY IS FIPRONIL TURNING UP IN EGGS?
It appears that Fipronil was mixed in with a red

mite treatment, Dega-16, in order to enhance its
effectiveness. Red mites are common pests on
poultry farms. Fipronil is not authorised to be used
around or on food-producing animals. How the
Dega-16 product became contaminated is unclear
and a criminal investigation is underway.
The contaminated eggs originated from Dutch farms. They have since been reported in 15 other countries and Hong Kong.
15
180 FARMS MILLIONS
TEMPORARILY OF EGGS WITHDRAWN
SHUT DOWN
IN THE NETHERLANDS FROM SALE
SHOULD I BE WORRIED ABOUT FIPRONIL?
? Ingestion of large amounts of fipronil can lead

to kidney, liver, and thyroid damage. However,
the amounts present in the contaminated eggs
are much lower, and at these levels it is unlikely
?
to be a risk to public health. In addition to this,
the ongoing investigation has established
that any affected products have already been
withdrawn from sale in the countries affected.
IN SHORT: LOW LEVEL EXPOSURE TO FIPRONIL IS UNLIKELY TO BE A HEALTH RISK. AFFECTED EGGS HAVE BEEN WITHDRAWN FROM SALE.
BUCKMINSTERFULLERENE
Sir Harry Kroto, one of the winners of the 1996 Nobel prize in chemistry, passed away recently.
Here, we take a look at the molecule that won him his Nobel prize, C60 , or Buckminsterfullerene.
C 60 – ‘BUCKYBALLS’ C 60 occurs naturally, and is

found in soot in small quantities.
It’s also been observed in space.
Football-shaped form of carbon It’s named after Buckminster
Fuller, an architect whose
geosedic domes it resembles.
Truncated icosahedron
12 pentagonal faces, 20 hexagonal faces
The first of the fullerenes to
be discovered, there are now
a number of recognised types,
Nobel Prize: 1996 including carbon nanotubes.
A BRIEF HISTORY OF BUCKMINSTERFULLERENE
Existence of the C 60 Astrophysicists Wolfgang Buckyballs detected in

molecule proposed by Krätschmer and Donald Huffman space; they could be
the Japanese scientist develop a method to make C60 in responsible for mystery
Eiji Osawa. larger quantities. interstellar absorptions.
1970 1990 2010
1985 1996
C 60 discovered during work Nobel prize in chemistry awarded
investigating carbon clusters to Harry Kroto, Robert Curl, and
formed in conditions similar to Richard Smalley, for discovery of
those in red giant stars. fullerenes (including C 60)

BY NC ND
THE FLINT WATER CRISIS
The American city of Flint, Michigan, has been in the news recently due to the discovery of very
high levels of lead in its water supply. But how did this lead get there? Here’s a brief explainer.
H TRIHALOMETHANES CORROSION: DETROIT VS. FLINT RIVER

Disinfectant byproducts; formed
Chloride to sulfate
X C by the reaction of chlorine

(added to disinfect the water) 0.45 VS 1.60 mass ratio (CSMR);
X with organic matter. 0.45 = low corrosion;
1.60 = very high
X X = halogen (commonly Cl or Br) DETROIT FLINT corrosion.
When high levels of trihalomethanes were detected in Flint’s water, ferric chloride (FeCl3)
was added to improve removal of organic matter. However, this increased the water’s
already high concentration of chloride ions, and as a result made the water more corrosive.
CORROSION CONTROL WITH PHOSPHATES WITHOUT PHOSPHATES
O
Pb Pb
Pb Pb
HO P OH Pb Pb
Pb
Pb
OH
Orthophosphates are added to water to reduce the amount of lead leaching into it from
pipes. They do this by forming a layer of low-solubility lead-phosphate complexes inside
the pipe. This method of corrosion control was not used for the Flint River water supply.

BY NC ND
JUPITER AND JUNO
NASA’s probe ‘Juno’, launched in 2011, entered orbit around Jupiter this week. Amongst other
things, it’s going to be investigating the planet’s chemical composition. Here’s what we know so far.
ATMOSPHERE METALLIC HYDROGEN

–
HYDROGEN 90% +
–
– +
+
–
– +
+
+
–
–
+
–
+
+
–
+ –
+
HELIUM ~10%
–
– +
HYDROGEN GAS METALLIC HYDROGEN
OTHER GASES <1% At the very high pressures in Jupiter,

hydrogen is thought to develop
metallic properties. This may be the
Including CH4, NH3, C2H6, H2O source of Jupiter’s magnetic field.
W H AT C AU S E S T H E CO LO U R O F J U P I T E R ’ S G R E AT R E D S P OT ?
N
H H + H C C H H C N
UV x y z
H
AMMONIA ACETYLENE CYANIDE-LIKE MOLECULES

NH3 C2H2 x, y and z vary
Scientists still aren’t 100% sure what causes the Great Red Spot’s colour. The most recent suggestion is that
UV light from the sun causes ammonia and acetylene gases in the top layers of clouds to react, producing
cyanide-like molecules. Previous suggestions implicated either sulfur or phosphine as the colour’s cause.

BY NC ND
THE NEW 12-SIDED £1 COIN
COMPOSITION
Cu
OUTER RING
NICKEL-BRASS Zn Ni
INNER RING Ni ?
NICKEL-PLATED ALLOY
The exact specification of the nickel-

plated alloy has not yet been revealed.
The new £1 coin arrives in the UK on 28th March 2017. One in thirty
£1 coins currently in circulation is a counterfeit; the new coin has
MASS: 8.75 GRAMS
security features that make it harder to counterfeit, including a THICKNESS: 2.8 MILLIMETRES
latent image that changes when viewed from different angles.
DIAMETER: 23.43 MILLIMETRES
© Andy Brunning/Compound Interest 2017 - www.compoundchem.com | Twitter: @compoundchem

C Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. Photo: The Royal Mint. BY NC ND
CHEMISTRY ADVENT 2017 1
THE SMELL OF CHOCOLATE
More than 600 chemical compounds have

been identified in chocolate. However, a
much smaller number of these actually
contribute to its flavour and aroma. The
structure of some of the chemicals that
have been identified as important aroma
contributors are shown below.
O R N R
O
O O R N R
3-METHYLBUTANAL VANILLIN PYRAZINES
Malty aroma; other aldehydes Aroma of vanilla. Vanillin is not A number of pyrazines
include 2-methylpropanal and found in cocoa beans, but often contribute nutty, cocoa, and
2-methylbutanal. added to chocolate products. earthy aromas.
Carbon O Oxygen N Nitrogen R Rest of molecule (variable) Hydrogen

Hydrogens on carbon atoms implied; each carbon has 4 bonds.
© Andy Brunning/Compound Interest 2017 - www.compoundchem.com | @compoundchem

BY NC ND
CHRISTMAS TREE AROMA
O BORNYL ACETATE
ALPHA-PINENE
BETA-PINENE
Hydrogens on carbon atoms implied;

Carbon O Oxygen each carbon has 4 bonds.
Several molecules contribute to the aroma of

Christmas trees. A key compound is pinene,
which exists as two isomers. Bornyl acetate also
contributes a fresh pine aroma and is commonly
used in pine fragrances and air conditioners.

BY NC ND
GINGERBREAD CHEMISTRY
O O
GINGEROL
ZINGERONE
Carbon O Oxygen Hydrogen

The compound gingerol gives fresh ginger its pungency. Zingerone lends
gingerbread its sweet, spicy flavour; this compound is not present in uncooked
ginger, but is created by the reaction of gingerol when it is heated.

BY NC ND
SILVER BAUBLES
Silver baubles for hanging on Christmas

trees are traditionally silvered using
silver nitrate solution. This is added
to the inside of the bauble, followed
by concentrated ammonia solution. A
glucose solution is then added, which
causes the reduction of the silver ions
to silver metal, producing a shiny silver
coating on the inside of the bauble.
–
O O O
+
Ag O
N O
O O O O
SILVER NITRATE GLUCOSE
Ag Silver Carbon O Oxygen N Nitrogen Hydrogen


BY NC ND
THE CHEMISTRY OF A CHRISTMAS CRACKER
– + –
Small amounts of silver fulminate, a highly
C N O
unstable compound, are placed on one of
+ the two strips of card in the cracker, and an
Ag abrasive agent is placed on the other. When
the cracker is pulled, the friction generated is
enough to detonate the silver fulminate.
SILVER FULMINATE
ABRASIVE AGENT
SILVER FULMINATE

BY NC ND
CANDY CANE CHEMISTRY
O
SUCROSE
O
O O Carbon
O O
O Oxygen
O
Hydrogen
O
O Note: hydrogens on
O carbon atoms implied;
O each carbon has 4 bonds.
Candy canes are created by boiling a mixture of water,

sugar (sucrose), and corn starch to create a syrup, to
which peppermint flavouring is added. Menthol is the
chemical in peppermint that makes your mouth feel
cold – it triggers cold-sensitive receptors.
MENTHOL
Triggers cold-sensitive TRPM8
receptors when it is eaten
– this can also occur if it is
applied to the skin or inhaled.
O

BY NC ND
MAKING FAKE SNOW

– +
O O Na
Carbon
O Oxygen
Na Sodium
n Hydrogens on carbon
atoms implied; each
carbon has 4 bonds.
SODIUM POLYACRYLATE
Sodium polyacrylate is a super-absorbant polymer that

can be used to create fake snow. It is a white powder
which can absorb 300 times its own weight in water.
When dry, the chains of

the polymer are coiled up.
When wet, the polymer

molecules dissociate
into negatively charged
carboxylate ions and
sodium ions. The negative
charges repel each other,
and the polymer expands.
WITHOUT WATER WITH WATER

BY NC ND
THE HOLLY AND THE IVY
O THEOBROMINE
Carbon
N
N O Oxygen
N Nitrogen
N
O N Hydrogen
Note: hydrogens on
carbon atoms implied;
each carbon has 4 bonds.
O
FALCARINOL
Holly berries contain bitter compounds called alkaloids, making them mildly toxic
if eaten. One of these alkaloids is theobromine, also found in chocolate in small
amounts. Common ivy contains a compound, falcarinol, which can cause moderate
allergic reactions in some people on skin contact. This differs from the compound
found in poison ivy, urushiol, which can also irritate the skin.

BY NC ND
THE RELIGHTING CANDLE TRICK
Here’s a fun trick for the Christmas dinner table: if you blow out a candle, then hold a lit
match in the ‘smoke trail’ coming off the extinguished flame, the candle will relight. The
‘smoke trail’ is actually wax vapour, and putting a lit match into it simply relights the
fuel, giving the illusion of the flame ‘jumping’ back down to the candle wick.
GENERAL EQUATION FOR C25H52 (g) + 38 O2 (g) 25 CO2 (g) + 26 H2O (g)
WAX COMBUSTION

BY NC ND
POINSETTIA PLANT INDICATOR

O O
+ O
O O O O –
O O
O O
O O
RED (AT pH <3) YELLOW GREEN (AT pH >8)
O O O
O
O O O O O O –
O O O
O O O
O O O
COLOURLESS (AT pH 3–4) VIOLET (AT pH 4–7) BLUE (AT pH 7–8)
Carbon O Oxygen Hydrogen Hydrogens on carbon atoms implied; each carbon has 4 bonds.
Poinsettias are often sold in the run-up to Christmas; as well as looking colourful
they can also be pH indicators! The anthocyanin compounds that give the leaves
their red colour can be extracted by boiling the leaves in water. This extract will
change colour in solutions of different acidities or alkalinities, as shown above.

BY NC ND
SNOW GLOBE CHEMISTRY
BENZOIC ACID
Solubility (25˚C): 3.44 grams per litre

Solubility (100˚C): 56.3 grams per litre

Benzoic acid can be used to make the ‘snow’ in snow globes. It’s quite
soluble in hot water, but isn’t very soluble in room temperature water.
When dissolved in hot water, as the water cools down it precipitates out
of solution and forms snow-like flakes.

BY NC ND
BELL METAL COMPOSITIONS
Ni Pb Fe
Cu Sn
NICKEL LEAD IRON
COPPER
75% TIN
20%
Sb Zn Bi
ANTIMONY ZINC BISMUTH
Various other elements, some of which are shown on the right, make up the balance of the percentage
Bells are commonly made of tin bronzes, essentially alloys of copper and tin
with other trace elements making up the balance. Some trace elements are
purposefully added to improve the material properties and sound. Trace elements
such as phosphorus and sulfur can make the bell more susceptible to cracking.

BY NC ND
CHRISTMAS LIGHT CHEMISTRY
RED YELLOW GREEN BLUE
GaAsP GaAsP GaP InGaN
AlGaInP AlGaInP GaN AlGaN
LEDs (light-emitting diodes) give off light when current is passed through them. They are made
from semiconducting materials; the colour of light emitted depends on the materials used. Many
of these materials are based on gallium, such as gallium arsenide phosphide (GaAsP), gallium
phosphide (GaP), gallium nitride (GaN), and aluminium gallium indium phosphide (AlGaInP).

BY NC ND
POISONOUS MISTLETOE
TYRAMINE
O
Carbon
Note: hydrogens
O Oxygen on carbon atoms
implied; each carbon
N Nitrogen has 4 bonds.
Hydrogen N
By all means kiss under the mistletoe this Christmas, but don’t be tempted to try and eat its
berries or leaves. They’re mildly toxic if ingested due to the presence of the toxic peptides
phoratoxin and viscotoxin, as well as the alkaloid tyramine shown above. While ingesting small
amounts of the berries isn’t deadly, it can lead to nausea and vomiting.

BY NC ND
MINCE PIE COMPOUNDS
O O
O
O
O O
Mince pies are a traditional part of

the British Christmas. Although,
as the name suggests, they once TARTARIC ACID
contained meat, today’s mince pies
contain dried fruits, suet, and spices.
O
Dried fruits contain a number of
fruit acids, such as malic acid from
apples, and tartaric acid from raisins,
which add to the tart flavour. Cloves
are a commonly used spice, in which O
eugenol is a key flavour contributor.

EUGENOL

BY NC ND
BRUSSELS SPROUTS CHEMISTRY
Brussels sprouts contain high levels of

glucosinolate compounds, such as sinigrin and
progoitrin. These are broken down into several
compounds when the tissue of the sprouts is
damaged, including isothiocyanates, which
contribute to the bitterness of sprouts. Studies
suggest sensitivity to this bitterness may have
a genetic component.

N Nitrogen S Sulfur K Potassium
O
– + O
O O S O K – +
O O O S O K
O N
O O N
O
O S
O S
O O O O
SINIGRIN PROGOITRIN

BY NC ND
THE AROMA OF FRANKINCENSE

O
OLIBANIC ACID ISOMERS

Frankincense is a dried resin used in incense. It has a distinctive smell

associated with churches and Christmas. The resin has several compounds that
contribute to its aroma, but chemists recently identified olibanic acid isomers
as the key chemicals which, despite only being present in trace amounts, are
responsible for the distinctive aroma of frankincense.

BY NC ND
WRAPPING PAPER & TAPE
Present wrapping requires both wrapping paper and tape – which have
more in common chemically than you might expect. Both are based
on cellulose, with tape also containing a pressure-sensitive acrylic or
synthetic rubber-based adhesive.
O
O
O
O O CELLULOSE
O O
O
O
O
n
Carbon O Oxygen Hydrogen Hydrogens on carbon atoms implied; each carbon has 4 bonds.

BY NC ND
CHRISTMAS TURKEY
A huge number of chemical reactions occur when you

stick your turkey in the oven, including the Maillard
reaction, which occurs between amino acids and sugars
in the meat during cooking.
Hundreds of products are formed by the Maillard
reaction. A small subset of basic types of these
compounds are shown below. Compounds called
melanoidins are also formed, which contribute to the
brown colouration that develops during cooking.
O
O N
N
O S
FURANS FURANONES PYRAZINES THIOPHENES

meaty, burnt flavours sweet, caramel-like cooked, roasted meaty, roasted
flavours flavours flavours
Carbon O Oxygen N Nitrogen S Sulfur Hydrogen


BY NC ND
CRANBERRY CHEMISTRY
O O
O
O O
QUERCETIN

Cranberries are high in polyphenol antioxidants, such as quercetin, and as a

consequence have a reputation as a health food. Lab tests have shown quercetin and
related compounds in cranberries to have anti-cancer effects, but evidence for these
effects in humans is currently limited, and more research is required.
Cranberry juice is often suggested as a treatment for urinary tract infections, but
reviews of several studies have shown it provides no benefits compared to a placebo.

BY NC ND
FLAMING CHRISTMAS PUDDINGS
ETHANOL

Christmas pudding is a traditional part of Christmas dinner, made from a

multitude of dried fruits flavoured with various spices. It’s also a tradition to
pour warmed brandy over the pudding and set it alight before serving.
It’s the alcohol (ethanol) vapour from the warmed brandy that burns. The blue
flame is due to complete reaction of the ethanol vapour with oxygen in the air.
O O O O O O O O
O + O O O O + O
ETHANOL OXYGEN CARBON DIOXIDE WATER

BY NC ND
THE SMELL OF CHOCOLATE
More than 600 chemical compounds have

been identified in chocolate. However, a
much smaller number of these actually
contribute to its flavour and aroma. The
structure of some of the chemicals that
have been identified as important aroma
contributors are shown below.
O R N R
O
O O R N R
3-METHYLBUTANAL VANILLIN PYRAZINES
Malty aroma; other aldehydes Aroma of vanilla. Vanillin is not A number of pyrazines
include 2-methylpropanal and found in cocoa beans, but often contribute nutty, cocoa, and
2-methylbutanal. added to chocolate products. earthy aromas.
Carbon O Oxygen O Nitrogen R Rest of molecule (variable) Hydrogen


BY NC ND
THE SMELL OF WINTER FIRES
O O
O O
GUAIACOL SYRINGOL
O
O
Carbon
O Oxygen O
O
Hydrogen
4-METHYLGUAIACOL each carbon has 4 bonds.
ISOEUGENOL
Smoke from winter wood fires contains hundreds of volatile compounds, a number
of which contribute to its aroma. Phenolic compounds are particularly important
contributors; syringol and guaicols have sweet, smoky aromas, whereas isoeugenol
has a spicy woody aroma. Phenol and cresols contribute pungent aromas.

BY NC ND
SLOE GIN CHEMISTRY
NEOCHLOROGENIC ACID CHRYSANTHEMIN
O O
O
O O
O
+
O O
O O
O
O
O
O
O O
O
(+)-CATECHIN
O
O
O
O
O O
O
Carbon Hydrogens on carbon
O O Oxygen atoms implied; each
carbon has 4 bonds.
O Hydrogen
Sloe gin is a seasonal drink created by soaking sloe berries in gin for several months.
Sloe berries contain a variety of phenolic compounds, a selection of which are shown
here. They are responsible for the bitter flavour of sloes and their astringency. Some,
such as chrysanthemin, also contribute to the colour of sloe berries.

BY NC ND
THE ORANGE PEEL FLAMETHROWER

D–LIMONENE Carbon each carbon has 4 bonds.
Oranges were traditionally given as Christmas gifts, and they still have an
association with the festive period. D-limonene has an orange-like aroma, and
is a major component in the rinds of citrus fruits such as oranges. Squeezing
the oils from the peel into a candle flame produces a small jet of flame, as the
limonene that the oils contain is very flammable.
THIS IS FUN TO TRY – BUT DO IT SAFELY, OVER A NON-FLAMMABLE SURFACE.

! USE A SMALL AMOUNT OF PEEL, AND HOLD IT NEXT TO THE FLAME (NOT OVER).

BY NC ND
THE CHEMICAL HISTORY OF TINSEL
Ag
PRE-1900
SHREDDED SILVER
POST-1900 Al Pb
ALUMINIUM LEAD
PRESENT H Cl
Carbon PVC
H Hydrogen
H H
Cl Chlorine n
Tinsel was originally made from strands of shredded silver when it was first
invented around 1610 in Germany. Later, flammable aluminium and poisonous
lead foil were both used. Modern tinsel is commonlymade from polyvinyl
chloride (PVC), thin strips of which are coated with a metallic finish.

BY NC ND
O O
O O O
O N
O
–
O
+
O O Na
O
n
–
O
O
+
Ag
N
O
O O
Ci N
Merry
O
O
N
O N
N
O O N
O
Christmas
FROM COMPOUND INTEREST
O
O
O
O
O
O
O
THE CHEMISTRY OF POINSETTIA PLANTS
Poinsettia Plants & pH
The poinsettia plant can be used to make an indicator solution to
test for pH. This is because the red leaves contain anthocyanin
pigments, the structure of which subtly changes at varying pH.
Red cabbage contains similar pigments, and as such can be also
be used. Some possible structures & colours are shown below.
OH
HO O+
OH
OH
OH
OH
OH HO O
OH
RED (pH < 3)
OH
O OH
HO O COLOURLESS (pH 3 - 4)
OH
O
OH
OH HO O
O-
VIOLET (pH 4 - 7)
OH
OH OH
OH
BLUE (pH 7 - 8)
HO O
O -
Poisonous Poinsettias?
OH
OH
Poinsettia plants have a false reputation for being poisonous. Whilst
eating a lot of the leaves could cause stomach pain and vomiting,
YELLOW-GREEN (pH > 8)
this is unlikely due to their awful taste!
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Photo: Public domain. Graphic shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. BY NC ND
METAL ION
FLAME TESTS
A flame test is an analytical procedure used by
chemists to detect the presence of particular LITHIUM SODIUM POTASSIUM RUBIDIUM CAESIUM CALCIUM
metal ions, based on the colour of the flame Li+ Na+ K+ Rb+ Cs+ Ca2+
produced.
HEAT
ABSORPTION
LIGHT
STRONTIUM BARIUM RADIUM COPPER IRON BORON

Sr2+ Ba2+ Ra2+ Cu2+ Fe2+/Fe3+ B3+
EMISSION
When heated, the electrons in the metal ion

gain energy and can jump into higher energy
levels. Because this is energetically unstable,
the electrons tend to fall back down to where
they were before, releasing energy as they do
so. This energy is released as light energy, and INDIUM LEAD ARSENIC ANTIMONY SELENIUM ZINC
as these transitions vary from one metal ion to In3+ Pb2+ As3+ Sb3+/Sb5+ Se2+/Se4+ Zn2+
another, it leads to the characteristic colours
given by each metal ion.
2014 COMPOUND INTEREST WWW.COMPOUNDCHEM.COM
INORGANIC COMPOUNDS AS PIGMENTS IN PAINTS
A NUMBER OF INORGANIC COMPOUNDS ARE USED AS PIGMENTS IN PAINTS. MANY OF THESE COMPOUNDS ARE COLOURED DUE TO THE ABSORPTION OF LIGHT ENERGY
BY ELECTRONS IN d ORBITAL SUBSHELLS, MEANING WE SEE COLOURS DEPENDING ON WHICH WAVELENGTHS OF LIGHT ARE NOT ABSORBED BY THE COMPOUND.
TITANIUM WHITE ULTRAMARINE BLUE

Titanium dioxide, TiO2 Na6Al4Si6S 4O20
CARBON BLACK COBALT VIOLET CERULEAN BLUE
ANTIMONY WHITE Cobalt (II) phosphate PRUSSIAN BLUE Cobalt (II) stannate
Carbon Antimony trioxide, Sb2O3 Ferric hexocyanoferrate, Fe7(CN)18
C Co3(PO4 )2 Co2SnO4
ZINC WHITE COBALT BLUE
Zinc Oxide, ZnO Cobalt (II) aluminate, CoAl2O4
CADMIUM YELLOW
Cadmium sulfide, CdS CADMIUM RED
CHROME GREEN VIRIDIAN GREEN CADMIUM ORANGE Cadmium selenide, CdSe
Chromium (III) oxide Hydrated chromium (III) oxide CHROME YELLOW Cadmium sulfoselenide
Lead chromate, PbCrO4
Cr2O3 Cr2O(OH)4 Cd2SSe RED OCHRE
ZINC YELLOW Iron (III) oxide, Fe2O3
Zinc chromate, ZnCrO4
2014 COMPOUND INTEREST - WWW.COMPOUNDCHEM.COM

TRANSITION METAL
ION COLOURS
3+ 2+ 3+ 4+ 5+ 2+ 3+ 6+
Transition metals form coloured compounds
and complexes. These colours can vary
depending on the charge on the metal ion,
and the number and type of groups of atoms
(called ligands) attached to the metal ion. In
aqueous solutions, the ions form complexes
with the colours shown to the right.
OH2
H2O OH2 TITANIUM VANADIUM CHROMIUM
Mn+ Ti V Cr
H2O OH2
OH2
HYDRATED TRANSITION METAL ION
Electrons are arranged around the nucleus of

the metal atom in orbitals. Transition metals,
unlike other metals, have partially filled d
orbitals, which can hold up to 10 electrons.
When ligands are present, some d orbitals 2+ 7+ 2+ 3+ 2+ 2+ 2+
become higher in energy than before, and
some become lower. Electrons can then move
between these higher and lower d orbitals by
absorbing a photon of light. This absorption
of light affects the percieved colour of the
compound or complex. The wavelength of the
light absorbed is affected by the size of the
energy gap between the d orbitals, which is
in turn affected by the type of ligand and the
charge on the metal ion. MANGANESE IRON COBALT NICKEL COPPER
Mn Fe Co Ni Cu
THE CHEMISTRY
OF FIREWORKS
Colours in fireworks are generated by pyrotechnic
stars, which produce coloured light when
ignited. The stars contain five basic ingredients: RED YELLOW
STRONTIUM SALTS
Strontium Nitrate ORANGE SODIUM SALTS GREEN
COLOUR-PRODUCING COMPOUNDS Strontium Carbonate Sodium Bicarbonate BARIUM SALTS
Strontium Sulfate CALCIUM SALTS Sodium Nitrate
Calcium Carbonate Barium Nitrate
Specific compounds which produce an intense colour Strontium Chloride Sodium Chloride Barium Carbonate
Calcium Chloride
when burned. Some of the commonly used colour Calcium Sulfate Barium Chloride
producing compounds are listed on the right; generally Barium Chlorate
they tend to be metal salts.
FUEL OXIDISER
Allows the star to burn; Usually nitrates, chlorates
gunpowder, which contains or perchlorates; required
a mix of potassium nitrate, to provide oxygen for the
sulfur and charcoal, is combustion of the fuel.
often used.
BINDER CHLORINE DONOR

Hold the mixture together;
the most commonly used
Chlorine donors can help
strengthen some colours.
BLUE SILVER
binder is a type of starch
called dextrin, dampened
Sometimes the oxidiser
can also act as the
COPPER SALTS
Copper (I) Chloride PURPLE WHITE HOT
MAGNESIUM &
WHITE
with water. chlorine donor. Copper Carbonate COMBINE COPPER BURNING METAL
Copper Oxides ALUMINIUM Magnesium
& STRONTIUM Aluminium
COMPOUNDS Titanium

FLAME TEST COLOURS
LITHIUM SODIUM POTASSIUM RUBIDIUM CAESIUM CALCIUM

Li+ Na+ K+ Rb+ Cs+ Ca2+

Sr2+ Ba2+ Ra2+ Cu2+ Fe2+/Fe3+ B3+
INDIUM LEAD ARSENIC ANTIMONY SELENIUM ZINC

In3+ Pb2+ As3+ Sb3+/Sb5+ Se2+/Se4+ Zn2+
A flame test is an analytical procedure used by chemists to detect the presence of

particular metal ions, based on the colour of the flame produced. When heated,
the electrons in the metal ion gain energy and can jump into higher energy levels.
Because this is energetically unstable, the electrons tend to fall back down to
where they were before, releasing energy as they do so. This energy is released as
light energy, and as these transitions vary from one metal ion to another, it leads
to the characteristic colours given by each metal ion.

pH INDICATOR COLOURS
0 2 4 6 pH 8 10 12 14
RED GREEN PURPLE
UNIVERSAL INDICATOR
NONE NONE PINK
PHENOLPHTHALEIN
RANGE: 8.3 - 10.0
RED YELLOW YELLOW
METHYL ORANGE
RANGE: 3.1 - 4.4
PINK YELLOW BLUE
THYMOL BLUE
RANGE: 1.2 - 2.8, 8.0 - 9.6
YELLOW GREEN BLUE
BROMOTHYMOL BLUE
RANGE: 6.0 - 7.6
YELLOW PINK PINK
PHENOL RED
RANGE: 6.4 - 8.0

THE CHEMISTRY OF GLOW STICKS
RED ORANGE YELLOW GREEN BLUE

N O N+
Cl-
CO2H
RHODAMINE B 5,12-BIS(PHENYLETHYNYL)NAPHTHACENE RUBRENE 9,10-BIS(PHENYLETHYNYL)ANTHRACENE 9,10-DIPHENYLANTHRACENE
O
O
H OH
O
O
HOW DO GLOW STICKS PRODUCE LIGHT?
O + O O 2 +
O
H
O O
When glow sticks are bent, the inner glass tube is broken,
DIPHENYL
releasing hydrogen peroxide solution. This then reacts OXALATE & DYE
SOLUTION
O with a diphenyl oxalate, producing 1,2-dioxetanedione;
O this product is unstable, & decomposes to carbon dioxide,
+ Dye 2CO2 + Excited Dye releasing energy. The energy is absorbed by electrons in
HYDROGEN
O dye molecules, which subsequently fall back to their ground PEROXIDE
O state, losing excess energy in the form of light.

THE CHEMISTRY OF FIREWORK COLOURS
RED YELLOW BLUE SILVER

STRONTIUM SALTS
Strontium Nitrate
ORANGE SODIUM SALTS
GREEN COPPER SALTS
Copper (I) Chloride PURPLE WHITE HOT WHITE
Sodium Nitrate BARIUM SALTS MAGNESIUM &
Strontium Carbonate CALCIUM SALTS Sodium Oxalate
Copper Carbonate COMBINE COPPER BURNING METAL
Strontium Sulfate Calcium Carbonate Barium Nitrate Copper Oxide ALUMINIUM Magnesium
Calcium Chloride
Cryolite Barium Carbonate & STRONTIUM Aluminium
Calcium Sulfate Barium Chloride COMPOUNDS Titanium
Barium Chlorate
COLOUR PRODUCERS FUEL OXIDISER BINDER CHLORINE DONOR

Gunpowder Composition
CH2OH CH2OH CH2OH
NO3 - Nitrate
O O O
Sr Ba Cu ClO3 - Chlorate
75% 15% 10% OH OH OH
ClO3 - Chlorate
OH
O O OH
Potassium Nitrate Charcoal Sulfur OH OH OH
n
Ca Na Mg KNO3 C S
- Perchlorate
ClO4 - Perchlorate
ClO4 Dextrin
ENERGY DENSITY
3 MEGAJOULES PER KG (common binder)
Metal compounds which produce Allows firework to burn; Usually nitrates, chlorates or Hold the mixture together; the Chlorine donors help strengthen
an intense colour when burned. gunpowder, (potassium nitrate, perchlorates; required to provide most commonly used is a starch, some colours. Some oxidisers can
Some are listed above. sulfur & charcoal), is often used. oxygen for the combustion of fuel. dextrin, dampened with water. also act as chlorine donors.

COLOURS OF P H INDICATORS
0 2 4 6 pH 8 10 12 14
UNIVERSAL INDICATOR
PHENOLPHTHALEIN
RANGE: 8.3 - 10.0
METHYL ORANGE
RANGE: 3.1 - 4.4
THYMOL BLUE
RANGE: 1.2 - 2.8, 8.0 - 9.6
BROMOTHYMOL BLUE
RANGE: 6.0 - 7.6
PHENOL RED
RANGE: 6.4 - 8.0
C 2014 COMPOUND INTEREST - WWW.COMPOUNDCHEM.COM

INORGANIC PAINT PIGMENT COMPOUNDS
A number of inorganic compounds can be used as pigments in paints. Many of these compounds are coloured due to the absorption of light
energy by electrons in d orbital subshells, meaning we see colours depending on which wavelengths of light are not absorbed by the compound.
CARBON BLACK CERULEAN BLUE CHROME GREEN COBALT VIOLET CADMIUM ORANGE
Carbon, C Cobalt (II) stannate, Co2SnO4 Chromium (III) oxide, Cr2O3 Cobalt (II) phosphate, Co3(PO4)2 Cadmium sulfoselenide, Cd2SSe
TITANIUM WHITE ULTRAMARINE BLUE VIRIDIAN GREEN CADMIUM YELLOW CADMIUM RED
Titanium dioxide, TiO2 Sulfur-containing sodium silicate, Na 6 Al4 Si6S 4O20 Hydrated chromium oxide, Cr2O3 Cadmium sulfide, CdS Cadmium selenide, CdSe
ANTIMONY WHITE PRUSSIAN BLUE CADMIUM GREEN CHROME YELLOW RED OCHRE
Antimony trioxide, Sb2O3 Ferric hexocyanoferrate, Fe7(CN)18 Cadmium sulfide & chromium (III) oxide Lead chromate, PbCrO4 Iron (III) oxide, Fe2O3
ZINC WHITE COBALT BLUE ZINC YELLOW

Zinc oxide, ZnO Cobalt (II) aluminate, CoAl2O4 Zinc chromate, ZnCrO4

THE CHEMISTRY OF GEMSTONE COLOURS
Gemstone colours stem from their chemical structures, which absorb different wavelengths of light. Their hardness is measured on the Mohs hardness scale (1-10).
PEARL TURQUOISE OPAL JADE PERIDOT GARNET

Formula: CaCO3 Formula: Al6 (PO4) 4 (OH) 8 .4H2O Formula: SiO2 .nH2O Formula: NaAlSi2O6 Formula: Mg2SiO4 Formula: Mg3 Al2 (SiO4) 3
Mohs hardness: 2.5–4.5 Mohs hardness: 5.0–6.0 Mohs hardness: 5.5–6.0 Mohs hardness: 6.5–7.0 Mohs hardness: 6.5–7.0 Mohs hardness: 6.5–7.5
Produced in soft tissue of shelled Colour caused by the presence ‘Play of colours’ caused by Colour from chromium and iron Colour caused by iron 2+ ions Colour caused by iron 2+ ions
molluscs. The thinner the layers of of copper ions coordinated to the interference and diffraction of impurities. The mineral nephrite replacing magnesium ions in replacing magnesium ions in
the pearl, the finer the lustre. hydroxide ions and water. light passing through structure. is also referred to as jade. some locations in the structure. some locations in the structure.
AMETHYST CITRINE TOURMALINE ZIRCON AQUAMARINE EMERALD

Formula: SiO2 Formula: SiO2 Formula: Na3Li3 Al6 (BO3) 3 (SiO3) 6F4 Formula: ZrSiO4 Formula: Be3 Al2 (SiO3) 6 Formula: Be3 Al2 (SiO3) 6
Mohs hardness: 7.0 Mohs hardness: 7.0 Mohs hardness: 7.0–7.5 Mohs hardness: 7.5 Mohs hardness: 7.5–8.0 Mohs hardness: 7.5–8.0
Colour caused by irradiation of iron The yellow colour of citrine is Colour due to manganese Many colours depending on Colour caused by iron 2+/3+ Colour caused by chromium
3+ ions in place of silicon in some due to the presence of either ions replacing lithium and impurities. Colourless forms are ions replacing aluminium ions in ions replacing aluminium in
locations in the structure. aluminium or iron impurities. aluminium ions in some sites. popular diamond substitutes. some locations in the structure. some locations in the structure.
SPINEL TOPAZ ALEXANDRITE RUBY SAPPHIRE DIAMOND

Formula: MgAl2O4 Formula: Al2SiO4 (F,OH)2 Formula: Al2BeO4 Formula: Al2O3 Formula: Al2O3 Formula: Cn
Mohs hardness: 7.5–8.0 Mohs hardness: 8.0 Mohs hardness: 8.5 Mohs hardness: 9.0 Mohs hardness: 9.0 Mohs hardness: 10
A variety of colours are possible, Pure topaz is colourless; blue & Colour caused by chromium ions Colour caused by chromium ions Colour caused by titanium and Colourless; can be faintly coloured
caused by impurities such as iron, brown varieties are caused by replacing aluminium in some sites. replacing aluminium ions in some iron ions replacing aluminium ions by the trapping of nitrogen or
chromium and nickel. atomic level imperfections. Colour varies in different light. locations in the structure. in some locations in the structure. boron atoms in the crystal.

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THE CHEMISTRY OF THE DIFFERENT COLOURs OF BLOOD
Red Blue Green Violet

HUMANS AND THE MAJORITY OF SPIDERS, CRUSTACEANS, SOME Some Segmented WORMS, SOME MARINE WORMS INCLUDING PEANUT
OTHER VERTEBRATES MOLLUSCS, OCTOPUSES & SQUID LEECHES, & SOME MARINE WORMS WORMS, PENIS WORMS & BRAChIOPODS
HAEMOGLOBIN HAEMOCYANIN CHLOROCRUORIN HAEMERYTHRIN
R R O
NH NH HN
H O
O2 O2 O
N N N N N
N N R O
Fe O N
HN Fe
HN Fe Fe N NH
N N N Cu Cu N N N
O NH N OO OO N
R N N
N N
HN HN H H
O OH O OH R R O OH O OH
HAEM B HAEMOCYANIN CHLOROCRUORIN HAEMERYTHRIN

(oxygenated form) (oxygenated form; R = histidine residues) (oxygenated form) (oxygenated form)
Haemoglobin is a protein found in blood, built up Unlike haemoglobin, which is bound to red Chemically similar to haemoglobin; the blood Haemerythrin is only 1/4 as efficient at oxygen
from subunits containing ‘haems’. These haems blood cells, haemocyanin floats free in the blood. of some species contains both haemoglobin & transport when compared to haemoglobin.
contain iron, and their structure gives blood its Haemocyanin contains copper instead of iron. chlorocruorin. Light green when deoxygenated, it In the deoxygenated state, haemerythtin is
red colour when oxygenated. Deoxygenated When deoxygenated, the blood is colourless, but is green when oxygenated, although when more colourless, but it imparts a violet-pink colour
blood is a deep red colour - not blue! when oxygenated, it gives a blue colouration. concentrated it appears light red. when oxygenated.

BY NC ND
TESTING FOR CATIONS: SODIUM HYDROXIDE & AMMONIA PRECIPITATES
SODIUM HYDROXIDE SOLUTION OR AQUEOUS AMMONIA SOLUTION CAN BE ADDED TO SOLUTIONS CONTAINING METAL IONS IN ORDER TO DISCERN THEIR IDENTITY. THE COLOUR
PRECIPITATE FORMED BY THE REACTION CAN BE USED TO DETERMINE THE METAL IDENTITY. IN SOME CASES, THE PRECIPITATE DISSOLVES IN EXCESS NaOH or NH3.
CALCIUM (Ca2+) CHROMIUM (Cr3+) MANGANESE (Mn2+) IRON (Fe2+) IRON (Fe3+)
Excess Excess Excess Excess Excess Excess Excess Excess Excess Excess
NaOH NH 3 NaOH NH 3 NaOH NH 3 NaOH NH 3 NaOH NH 3
COBALT (Co2+) NICKEL (Ni2+) COPPER (Cu2+) ZINC (Zn2+) ALUMINIUM (Al3+)

THE CHEMISTRY OF AUTUMN LEAF COLOURS
CHLOROPHYLL CAROTENOIDS & FLAVONOIDS CAROTENOIDS ANTHOCYANINS & CAROTENOIDS

OH OH
OH
HO
N N LUTEIN HO O+
ß-CAROTENE
A type of carotenoid A type of carotenoid
Mg
N N Carotenoids and flavonoid pigments are always Sugar

Carotenoids also contribute orange colours.
present in leaves, but as chlorophyll is broken OH
Beta-carotene is one of the most common
down in the autumn their colours come to the
carotenoids in plants, and absorbs green and ANTHOCYANINS
fore. Xanthophylls, a subclass of carotenoids, are
C20H39 blue light strongly, reflecting red and yellow light (general structure)
responsible for the yellows of autumn leaves.
O and causing its orange appearance. It is also
O O One of the major xanthophylls, lutein, is also the
responsible for the orange colouration of carrots. Anthocyanin synthesis is kick-started by the
O compound that contributes towards the yellow
O colour of egg yolks. Carotenoids in leaves start degrading at the same onset of autumn. As sugar concentration in the
time as chlorophyll, but they do so at a much leaves increases, sunlight initiates anthocyanin
CHLOROPHYLL A
A type of chlorin slower rate; some fallen leaves can still contain production. The purpose they serve isn’t clear; it
measurable amounts. is suggested that they may play a light-protective
role. It was previously thought they might delay
Chlorophyll gives plant leaves their green colour. O O leaf fall, but this has been discounted.
Plants require warm temperatures and sunlight OH
to produce chlorophyll. In autumn, the amount O

OH
produced begins to decrease, and existing O
chlorophyll is slowly broken down, diminishing the O O HO
green colour of the leaves. FLAVONOL FLAVONE VIOLAXANTHIN LYCOPENE

(general structure) (general structure) A type of carotenoid A type of carotenoid
© Andy Brunning/Compound Interest 2018 - www.compoundchem.com | Twitter: @compoundchem | FB: www.facebook.com/compoundchem

Ci This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. BY NC ND
SCIENCE & TECHNOLOGY
PeriodicGraphics
CEN.ACS.ORG 32 S E PTE M BE R 2 1 , 20 1 5
Periodic graphics
More
online
To see more of
Brunning’s work, go
to compoundchem.
com. To see all of
Andy Brunning, author of the popular C&EN’s Periodic
Graphics, visit cenm.
graphics blog Compound Interest ag/periodicgraphics.
JANUARY 16, 2017 | CEN.ACS.ORG | C&EN 23

THE CHEMISTRY OF HIGHLIGHTER COLOURS
YELLOW BLUE ORANGE PINK
-
Na+
O O- Na+
O O
CH3 S
O S O O HO
N O
Na+ Na + O
- O -
O S H H O
O O N N
S O -
O O +
S Na+ O N+ Cl-
O O - S
O O
N N N O N+
OH
O N+
PYRANINE - SOLVENT GREEN 7 ACID BLUE 9 SOLVENT RED 49
(Pyrene dye) (Triphenylmethane dye)
O Cl- (Rhodamine dye)
BASONYL RED 485 (TOP) & BASIC YELLOW 40

Pyranine, a pyrene dye, is the dye commonly A triphenylmethane dye such as Acid Blue 9 is (Xanthene dye and Coumarin dye) A rhodamine dye can impart a pink colour to
used in yellow highlighters. Fluorescein can commonly used to achieve a blue ink colour; it the highlighter ink. A rhodamine dye can also be
also be used. Mixing a pyrene dye with a is used in combination with a colour-brightening A mix of a xanthene dye and a coumarin dye is combined with a triphenylmethane dye in order
triphenylmethane dye gives a green ink. compound, e.g. an anionic stilbene derivative. required to achieve an orange colour. to produce a purple-coloured highlighter.

MAKING AN INDICATOR FROM RED CABBAGE
The compounds that give red cabbage its colour can be extracted and used as a pH indicator solution. Here we look at the method and the colours!
MAKING THE INDICATOR
ROUGHLY CHOP
THE CABBAGE
BOIL FOR A 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14
FEW MINUTES
ACIDIC pH ALKALINE
O O O O
3 + O
O O O O O O – O O –
O O O O
STRAIN AND O O O O
LET COOL O O O O
RED (pH <3) VIOLET (pH 4–7) BLUE (pH 7–8) YELLOW GREEN (AT pH >8)

4
The red cabbage extract can be used to determine whether substances are acidic or
USE AS AN alkaline. The structures of the anthocyanin pigments which give the red cabbage its colour
INDICATOR! are subtly changed at varying pH. These different structures give a range of colours.

THE CHEMISTRY OF BODILY FLUID COLOURS
Blood, urine, and faeces are quite distinct. However, the compounds that give them their colours are chemical relatives! We take a look at them here.
BLOOD: HAEMOGLOBIN BILE: BILIVERDIN & BILIRUBIN

CH2 CH3 H2C CH3 H 2C CH3
CH2 O O O O
Haemoglobin is a protein H3C
NH HN
H3C
NH HN
H3C CH2 CH2
O2
found in blood, built up of BILIVERDIN
N N NH N NH HN
smaller sub-units containing H3C CH3 H3C CH3
Fe BILIRUBIN
‘haems’. These haems contain
N N iron, and their structure gives COOH COOH COOH COOH
H3C CH3 our blood its red colour when
oxygenated.
Haem in old and damaged red blood cells can
be broken down, first into the green pigment
As blood dries it gradually
O OH O OH biliverdin, which itself is converted to the brown
turns brown, as haemoglobin is
pigment bilirubin. Both are found in bile, and can
oxidised to methaemoglobin.
HAEM B also cause the colouration around bruises.
URINE: UROBILIN FAECES: STERCOBILIN

COOH COOH COOH COOH
H3C CH2 H3C CH3
H3C H3C CH3 H3C H3C H3C CH3 H3C
UROBILIN STERCOBILIN
O O O O
N N N N N N N N
H H H H H H
Bilirubin is broken down by microbes in the intestines, Urobilinogen produced by breakdown of bilirubin in the
producing urobilinogen. This can then be absorbed into the intestines can continue through the digestive system and
bloodstream, and oxidised to produce urobilin. Urobilin is be reduced to stercobilin. This is excreted from the body in
excreted by the kidneys, and gives urine its yellow colour. the faeces, and is responsible for their brown colouration.

THE CHEMISTRY OF COLOURED GLASS
Glass is coloured in 3 main ways. It can have transition or rare earth metal ions added; it can be due to colloidal particles formed in the glass; or
it can be due to particles which are coloured themselves. This graphic shows some of the typical chemical elements that are used to colour glass.
SODA-LIME GLASS
COMPOSITION
SiO2 70-74%
SILICON DIOXIDE
CaO 10-14%
CALCIUM OXIDE IRON IRON-SULFUR COPPER CHROMIUM NICKEL GOLD COPPER-TIN
2+ 2+ 3+ 2+
Fe Fe-S Cu Cr Ni Au Cu-Sn
Na2O 13-16%
SODIUM OXIDE
Soda-lime glass is the
most common glass
type, making up an
estimated 90% of all
manufactured glass. Its
uses include containers,
windows, bottles, and
drinking glasses. The
above percentages are MANGANESE COBALT URANIUM NEODYMIUM Erbium SELENIUM-CADMIUM CADMIUM
Mn 3+
Co2+
U 4+/5+/6+
Nd 3+ 3+
Er Se-Cd as CdS
a general composition
only; other compounds
These are typical colours, and can be affected by the type of glass as well as the concentration of the colourant.
are also present in
smaller amounts. Combination with other elements and compounds can also have an effect on the final colouration of the glass.

THE CHEMISTRY OF LED LIGHTS
LED lights come in a full range of colours – this graphic takes a closer look at the chemistry behind how their light and varied hues are achieved.
RED ORANGE YELLOW GREEN BLUE VIOLET
GaAsP GaAsP GaAsP GaP InGaN InGaN
AlGaInP AlGaInP AlGaInP GaN AlGaN AlGaN
GaP GaP GaP InGaN ZnSe GaN
HOW DO LEDS WORK? HOW ARE DIFFERENT COLOURS MADE?

P-TYPE
Light emitting diodes (LEDs) use semiconducting

materials to produce light and colour. Many of the BLUE
GREEN
materials used are based on gallium, such as gallium ORANGE RED
POWER
phosphide (GaP) and gallium nitride (GaN).

LIGHT
Layers of the semiconductor are "doped" with
impurities. This creates an n-type layer, which has A variety of colours are made possible by the use of
electrons spare, and a p-type layer, which has different semiconducting materials, and "doping"
electron "holes". When a current is applied, electrons them with different types and amounts of impurities.
from the n-type layer combine with the "holes" in the This affects the energy gap between the n-type
p-type layer. When the electrons fall into these holes,
N-TYPE and p-type layers, affecting the wavelength of light
they release energy in the form of visible light. produced when a current passes through the LED.

THE CHEMISTRY OF PERMANENT HAIR DYES
There are a number of different types of hair dyes, but the most commonly used are permanent (oxidative) dyes. These dyes have a range of different
components that react with each other to produce the desired end colour. In this graphic, we examine some of these chemicals, and how they form dyes.
1 PRIMARY INTERMEDIATES 3 COUPLING AGENTS
H2N NH2 H2N OH

NH2 H 2N NH2
HO OH HO NH2
PARAPHENYLENEDIAMINE (PPD) & PARA-AMINOPHENOL H2N OH H2N O

All permanent hair dyes contain a ‘primary intermediate’;
these are often p-diamines or p-aminophenols. They are
oxidised by hydrogen peroxide to give reactive species RESORCINOL m-AMINOPHENOL 2-METHYL-5-AMINOPHENOL p-PHENYLENEDIAMINE 2,4-DIAMINOANISOLE
GREENISH YELLOW LIGHT BROWN MAGENTA DARK BROWN PURPLE-BLUE
which then go on to react with couplers to produce dyes.
The exact structure of the reactive species produced by
oxidation is still the subject of some debate.
OH
N
HO NH2 OH
H2N NH2
2 OTHER COMPOUNDS OH
O H2 N
O
HO
OH
H HO
N 1,5-DIHYDROXYNAPHTHALENE 4-METHOXY-3-AMINOPHENOL 2,4-DIAMINOPHENOXYETHANOL m-DIETHYLAMINOPHENOL p-AMINO-o-CRESOL
O O H H BLUE-VIOLET GREEN DARK BLUE OLIVE BROWN DARK RED
H H NH2
Coupling agents, also referred to as colour couplers, are the other component in the dye mixture. Independently,
HYDROGEN PEROXIDE, AMMONIA, & ETHANOLAMINE they contribute little in the way of colour, but they can react with primary intermediates in the presence of an
oxidising agent to produce dye molecules, some examples of which are shown below. Most dyes will contain a mix
Hydrogen peroxide is the agent responsible for oxidation of different coupling agents, rather than just one. Primary intermediates can, in some cases, couple to themselves
of primary intermediates, and also lightens the natural to produce colouration. In the end, multiple different dye products are formed from a single formulation of hair dye.
pigments present in the hair, the melanins eumelanin and
H H N
pheomelanin. The dye-forming reactions are carried out N N N N
at an alkaline pH, which is why ammonia is also required
in the dye mixture. This raised pH causes the hair cuticle
H2N HO O NH2 H2N H2N O NH2 H2N H2N O
to swell, which in turn allows hydrogen peroxide and dye
molecules to pass into the cortex. Ethanolamine can be
GREEN INDO DYE BROWN INDO DYE MAGENTA INDO DYE
used as an alternative, milder alkaline agent. FROM PPD & RESORCINOL FROM PPD & m-AMINOPHENOL FROM PPD & 2-METHYL-5-AMINOPHENOL

THE CHEMISTRY OF POINSETTIA PLANTS
Poinsettia Plants & pH
The poinsettia plant can be used to make an indicator solution to
test for pH. This is because the red leaves contain anthocyanin
pigments, the structure of which subtly changes at varying pH.
Red cabbage contains similar pigments, and as such can be also
be used. Some possible structures & colours are shown below.
OH
HO O+
OH
OH
OH
OH
OH HO O
OH
RED (pH < 3)
OH
O OH
HO O COLOURLESS (pH 3 - 4)
OH
O
OH
OH HO O
O-
VIOLET (pH 4 - 7)
OH
OH OH
OH
BLUE (pH 7 - 8)
HO O
O -
Poisonous Poinsettias?
OH
OH
Poinsettia plants have a false reputation for being poisonous. Whilst
eating a lot of the leaves could cause stomach pain and vomiting,
YELLOW-GREEN (pH > 8)
this is unlikely due to their awful taste!

THE CHEMISTRY OF SPARKLERS
METALLIC FUEL EJECTION OF BURNING METAL PRODUCES SPARKS
Aluminium & Iron Titanium Ferrotitanium

Magnesium
THE POWDERED METALS REACT WITH O2 , AND PRODUCE METAL OXIDES
OXIDISERS PRODUCE OXYGEN TO BURN THE MIXTURE
NO3- Nitrate ClO3- Chlorate ClO4 - Perchlorate
BINDERS HOLD MIXTURE TOGETHER COLOURANTS METAL SALTS

CH2OH CH2OH CH2OH
O O O Sr Ba Cu Ca Na
OH OH OH Dextrin
(common binder)
OH O O OH OPTIONAL; CHLORIDE AND NITRATE
OH OH n OH
SALTS ARE COMMONLY USED

C Photo: Creative Commons BY license, Nina Hale (https://www.flickr.com/photos/94693506@N00/)
BY NC ND
THE COLOUR OF ALEXANDRITE
MAIN LOCATIONS
absorbance
350 nm wavelength of light 800 nm
ALEXANDRITE STRUCTURE
absorbance
chemical formula: Al2BeO4
= Al = BeO4 tetrahedra
CHROMIUM
Cr3+ Al3+ IMPURITIES
(occurs in <0.5% of aluminium sites)
ALEXANDRITE LIGHT TYPE LIGHT SPECTRUM

Alexandrite’s colour is formula: Al2BeO4 solid line: alexandrite absorbance
due to small amounts
of chromium impurities. Alexandrite appears blue-green in sunlight because not much blue or green
These cause it to absorb light is absorbed. In incandescent light, alexandrite appears purple-red; this
some colours of light while is because incandescent light contains a greater amount of red light than
others pass through. sunlight, as well as much less blue and green light.

THE CHEMISTRY OF FAKE TAN
Sunless tanning has become a popular way of getting a tanned look for the summer without the potential skin damage from
sun exposure. This graphic takes a look at how fake tanning products work, and some of the safety concerns surrounding them.
TAN LOTION CHEMICALS O

O
OH
HO
HO OH
OH
DIHYDROXYACETONE ERYTHRULOSE
a.k.a. DHA - most often used in combination
commonly used with DHA
LAStS 3-10 DAYS 1-15% DHA The ‘tan’ produced by tanning
2-4 HOURS TO APPEAR % USUALLY 5% IN STORE

lotions only has an SPF of around
3. Because of this, many tanning
lotions also contain some sun
Darkens for around 24 to 72 hours The FDA approved DHA for use in block in their formulations in order
after application. Erythrulose takes tanning lotions in 1977. Use in spray to help guard against UV light from
longer to develop its full effect. tanning booths isn’t approved. the sun.
1 2 3
REACTS
APPLIED TAN
HOW IT WORKS
The DHA in tanning lotions reacts with amino acids in the dead layer of skin on
the skin’s surface. This occurs via the Maillard reaction - the same type of reaction
that occurs in baking and roasting of foods such as meat during cooking. This
reaction leads to the production of melanoidins, which are the chemicals that
cause the appearance of a tan.
THE CHEMICALS USED IN FAKE TANNING PRODUCTS ALSO HAVE SOME POTENTIAL RISKS;
PARTICULARLY IN SPRAY TAN BOOTHS, WHERE THERE IS THE POSSIBILITY OF INHALATION.
POTENTIAL MUTAGEN? UV ABSORPTION SKIN ABSORPTION

Conflicting evidence.
Not at tanning lotion
concentrations.
UV Skin more sensitive to
ultraviolet light for 24hrs
after application.
11% Some DHA is absorbed into
living layers of skin. Effects
unknown.

BY NC ND
COSMETIC CHEMISTRY – RED LIPSTICK
OTHER DYES,
CASTOR
65% OIL 15% BEESWAX 65%
10% WAXES 5% LANOLIN 5% PIGMENTS &
PERFUME
Note that these figures are for an average composition. Actual composition varies from brand to brand, and there is likely to be some deviation from these percentages.
WAXES & OILS PIGMENTS & DYES

OH O
Waxes provide the structure of lipstick. A number of OH
different natural waxes are used, including beeswax, HO OH
Carnauba wax, and Candelila wax. Carnauba wax has O
the highest melting point of any wax, and is therefore O OH Br Br
HO
important to prevent lipstick from melting too easily.
Waxes also give emollient properties and glossiness. OH O O
HO OH HO O O
OH Br Br
CARMINE RED EOSIN
The approximate number of chemical
284 compounds that make up beeswax. Lipstick colour originates from a range of different pigments and dyes. Carmine red is a
pigment derived from scale insects. Eosin, also known as D&C Red No. 22, is a dye which
O
reacts with the amino groups in the proteins of the skin to produce a deep red colour. Titanium
dioxide can be used to dilute colours and give pink shades.
O
TRIACONTYL PALMITATE OTHER COMPOUNDS

One of the principal chemical components of beeswax
A number of other compounds are also added to lipstick; this can include different fragrances,
Oils give lipstick its gloss, and also provide lubrication to mask the smell of the other chemicals present. Also, capsaicin, the compound found in chilli
for the application of the lipstick. Castor oil is the most peppers, is sometimes included, as its skin irritant effect can induce plumping of the lips in
common, though other synthetic oils are also used. small quantities.
OH O OH
CAPSAICIN
OH H Major capsaicinoid compound
N found in chilli peppers
RICINOLEIC ACID O
Major component of castor oil (90% of fatty acid content)
O

THE CHEMISTRY OF MOISTURISERS
Whether you’re suffering from sunburn in the summer, or dry skin in the winter, moisturisers are on hand to help. This graphic takes a look at some
of the different compounds that moisturisers combine, and how each of the groups of compounds act to help produce a moisturising effect.
SKIN & WATER LOSS

OCCLUSIVE BARRIER
O O
H H TEWL H H
O O PETROLATUM Mixture of hydrocarbons with 25+ carbon atoms

H H H H Other occlusives include lanolin & silicones
O
EPIDERMIS H H
EPIDERMIS Occlusive agents prevent water loss by forming a

DERMIS hydrophobic barrier over the stratum corneum (the upper
layer of the epidermis). Vaseline is an example of an occlusive
HYPODERMIS
OCCLUSIVES moisturiser. Though effective, they make skin feel greasy.
The skin has 3 main layers. The OH OH

middle layer, the dermis, has several H
O
H
OH
roles which include storing water. OH
Transepidermal water loss (TEWL) is a
HO OH HO
EPIDERMIS
normal process of water loss through OH OH
the epidermis; moisturisers aim to
Other humectants include urea,
reduce this water loss. O O
GLYCERIN (L) & SORBITOL (R) sodium lactate, & hyaluronic acid
H H H H
O
H H
Humectants are hydrophilic, and help draw water from the
THE EPIDERMIS DERMIS dermis to the epidermis. At humidity higher than 80%, they
can also draw water from the atmosphere. Evaporation from
CHOLESTEROL
HUMECTANTS skin as a result can also cause extra dryness, however.
25
CERAMIDES 50
10 FATTY ACIDS O
15 OH H
OTHER O
EMOLLIENT LAYER H H
Approx. lipid composition of stratum corneum
HO
The epidermis is composed of five Others: ceramides,

GLYCOL STEARATE (L) & CHOLESTEROL (R)
sub-layers. The uppermost of these is H
O
H H
O
H
squalene, & fatty acids.
O
the stratum corneum, which is made H H
up of dead skin cells surrounded by Like occlusives, emollients can form a barrier to TEWL when
proteins. Ceramides, fatty acids and EPIDERMIS applied heavily. They can also reduce TEWL by helping ‘plug’
cholesterol fill the gaps between cells, the gaps between corneocytes (dead skin cells), replacing
limiting transepidermal water loss. EMOLLIENTS absent natural skin lipids, and help smooth roughened skin.

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 licence. BY NC ND
DEODORANTS VS. ANTIPERSPIRANTS
Deodorants and antiperspirants both help fight body odour – but they both do so in different ways. This graphic takes a look at what each of them
do to prevent body odour, how they do it, and some of the different chemical compounds that they employ to keep you from smelling terrible!
DEODORANTS ANTIPERSPIRANTS
Deodorants help to reduce body odour by targeting the Antiperspirants fight body odour by cutting down
bacteria under your arms that produce the various bad- on sweating. They do this by including aluminium or
smelling compounds. Some do this using anti-bacterial zirconium-based compounds that form a polymeric
compounds such as triclosan. Both deodorants and plug that physically blocks perspiration from being able
antiperspirants often use cyclomethicones, which are to escape sweat glands. This plug slowly breaks down
fast-drying silicone compounds, as solvents. over time, so reapplication can be required.
Cl O
TRICLOSAN PORE
O EPIDERMIS
Antibacterial compound
Another commonly used
antimicrobial compound is
Cl Cl chlorhexidine.
DERMIS
CYCLOMETHICONES
Solvent compounds
Si
O e.g. cyclopentasiloxane SWEAT GLAND
O Si
More common than alcohol
Si
solvents, which can also
O O
be used. Compounds such
AlnCl(3n-m)(OH)m Al(HCOO)3
as sodium benzoate are
Si Si ALUMINIUM CHLOROHYDRATE ALUMINIUM FORMATE
also present to act as a
O preservative and help to
extend the shelf life of the Al4Zr(OH)12Cl4 Gly . nH2O
product.
ALUMINIUM ZIRCONIUM TETRACHLOROHYDREX GLYCINE
(solid filled atoms represent carbon; smaller outlined atoms represent hydrogen)

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives Internation 4.0 licence. BY NC ND
THE CHEMISTRY OF SUNSCREEN
Summer sun brings with it the risk of sunburn, so we’ll all be slapping on the sunscreen to guard against it. But what
are the chemicals that keep you from turning as red as a lobster? This graphic looks at them and how they work.
TYPES OF UV RADIATION
UVA 320-400nm
wavelength
17
SUNSCREEN ACTIVE
Accounts for 95% of solar UV radiation reaching
INGREDIENTS
Earth’s surface. Penetrates deepest into skin, and APPROVED
contributes to skin cancer via indirect DNA damage. IN THE USA
wavelength
UVB 290-320nm
Accounts for 5% of solar UV radiation reaching
Earth’s surface. Causes direct DNA damage, and
is one of the main contributors to skin cancer. 28
wavelength SUNSCREEN ACTIVE
UVC 290-100nm
Filtered out by ozone in the Earth’s atmosphere,
INGREDIENTS
APPROVED
IN THE EU
and as a result does not reach the surface of the
Earth, and doesn’t cause skin damage.
Inorganic chemicals in sunscreen, such as zinc oxide and titanium oxide,

both absorb and scatter UV light. Organic chemicals are also used –
the chemical bonds in these absorb UV radiation, with the chemical
structure affecting whether they absorb UVA, UVB, or both. Several
different chemicals are used in sunscreen to ensure full protection.
UVA BLOCKERS UVB BLOCKERS UVA & UVB BLOCKERS

O O O O
O
O
O
OCTYL METHOXYCINNAMATE O OH
AVOBENZONE
OXYBENZONE
O O
O O HO
S
NH2 O
NH2
OH O O
O OH
MENTHYL ANTHRANILATE HOMOSALATE SULISOBENZONE
O
HO
S
OTHER UVB BLOCKERS OTHER UVA & UVB BLOCKERS
O (Italicised = not approved in USA) (Italicised = not approved in USA)
O
PABA Octylocrylene Dioxybenzone Neo Heliopan AP
O Padimate O Ensulizole Mexoryl XL Uvinul A Plus
O Cinoxate Octyl triazone Tinosorb S UVAsorb HEB
S
OH Octyl salicylate Enzacamene Tinosorb M
O
ECAMSULE Trolamine salicylate Amiloxate All currently approved in EU, Canada & Australia

BY NC ND
THE CHEMISTRY OF NAIL POLISHES
FILM-FORMING POLYMERS PIGMENTS & OTHER AGENTS
NO2 O2N Pigments in nail polish are either inorganic
O pigments (such as iron oxide) or organic
O2N O (carbon-based) pigments. Thermochromic and
O O O photochromic pigments are also possible.
O O O
O2N O
THERMOCHROMIC NAIL POLISH
O2N O COLD HOT
NO2
NITROCELLULOSE
n SOLVENTS & PLASTICISERS PHOTOCHROMIC NAIL POLISH
O O O
Conventional nail polish contains a polymer
dissolved in a solvent. When applied the solvent Pearlescent effects are due to materials such as
evaporates and the polymer forms a film. The O O
titanium dioxide and mica. Some polishes also
most common polymer is nitrocellulose. contain glitter. Thickeners (e.g. stearalkonium
ETHYL ACETATE BUTYL ACETATE ACETONE
hectorite) suspend these in the polish.
O BENZOYL PEROXIDE O
O
O R Ethyl acetate and butyl acetate are commonly used O WITHOUT
O
O
METHACRYLATE solvents, and give nail polish its characteristic smell. Ethyl
acetate and acetone are used in nail polish removers.
UV LIGHT Plasticisers (below) stop polish from cracking or chipping.
WITH
PHOTOINITIATOR MONOMER POLYMER BENZOPHENONE-1
DIBUTYL PHTHALATE
O O
O O
Gel nail polish is made up of methacrylate Previously used as a P As some nail polishes can last for up to two
monomers and a photoinitiator such as benzoyl plasticiser but phased out O weeks, stabilisers are added to prevent the
peroxide. Exposed the mixture to UV light due to health concerns. Its polishes changing colour when exposed to
use in nail polish is now
triggers polymerisation and solidification. CAMPHOR TRIPHENYLPHOSPHATE
sunlight. Benzophenone-1 is commonly used.
banned in the EU.

PeriodicGraphics
A collaboration between C&EN and Andy Brunning, author of the popular graphics blog Compound Interest
(compoundchem.com). To see all of C&EN’s Periodic Graphics, visit http://cenm.ag/periodicgraphics.
CEN.ACS.ORG 31 JANUARY 1 1 , 20 16
PeriodicGraphics
A collaboration between C&EN and Andy Brunning, author of the popular graphics blog Compound Interest
(compoundchem.com). To see all of C&EN’s Periodic Graphics, visit http://cenm.ag/periodicgraphics.
C EN.ACS.ORG 39 FE BRUARY 2 2 , 20 16
TWELVE WOMEN IN CHEMISTRY
CAROLYN BERTOZZI DARLEANE HOFFMAN JENNIFER DOUDNA
CHEMICAL BIOLOGIST NUCLEAR CHEMIST MOLECULAR BIOCHEMIST
Bertozzi researches the role of sugars Hoffman was one of the researchers Doudna was a leading figure in the
on the surface of cells in diseases such who confirmed the existence of element development of CRISPR gene editing,
as cancer, and develops technology to 106, Seaborgium. She also captured and technology that could in future lead to
advance biomedical research. analysed elements heavier than uranium. treatments for a range of diseases.
ADA YONATH CAROL ROBINSON TU YOUYOU

CRYSTALLOGRAPHER PHYSICAL CHEMIST PHARMACEUTICAL CHEMIST
Yonath’s research on the structure of The first female chemistry professor at Won a Nobel Prize in Medicine for her
the ribosome, which helps cells build both Cambridge and Oxford University. discovery of artemisinin, a compound
proteins, won her a Nobel Prize. She also Uses mass spectrometry to reveal the derived from the wormwood plant and
worked on modes of action of antibiotics. structure and reactivity of proteins. used as an drug to treat malaria.
SUSAN SOLOMON PRATIBHA GAI LESLEY YELLOWLEES

F
ATMOSPHERIC CHEMIST MATERIALS CHEMIST INORGANIC CHEMIST
Cl C Cl
Solomon’s work helped confirm that Gai co-invented a type of microscope that The first female president of the Royal
chlorine-containing compounds deplete allows visualisation of reactions at the Society of Chemistry. Her research
Cl ozone, and explained why this depletion atomic scale. She chose not to patent it so focuses on electron transfer reactions,
was focused over the Earth’s poles. it could be easily used by others. solar energy, and EPR spectroscopy.
PAULA HAMMOND JACQUELINE BARTON POLLY ARNOLD

CHEMICAL ENGINEER BIOPHYSICAL CHEMIST ORGANOMETALLIC CHEMIST
Hammond’s research focuses on Barton studies the chemical and physical Arnold’s research focuses on synthetic
nanoscale polymers for drug delivery and properties of DNA, and the role of charge chemistry and theories of bonding and
other applications. She co-founded the transport chemistry in DNA repair. She has reactivity, with the aim of understanding
MIT Institute for Soldier Nanotechnology. received numerous awards for her work. the behaviour of nuclear waste.

MORE WOMEN IN CHEMISTRY HISTORY
ELIZABETH FULHAME JANE MARCET ANNA SUNDSTRÖM
BORN ? DIED ? BORN 1769 DIED 1858 BORN 1785 DIED 1871
The first person to describe catalytic Published ‘Conversations on Chemistry’, Thought to have been the first woman
processes in her only publication in 1794. the most popular 19th century chemistry chemist in Sweden. Worked with Jöns
She also stained cloth with light sensitive textbook. A standard text in U.S. girls’ Jacob Berzelius, but her employment was
silver salts, later used in photography. schools, it also inspired Michael Faraday. forcibly ended when Berzelius married.
ANNA VOLKOVA ELLEN SWALLOW RICHARDS AGNES POCKELS

BORN ? DIED 1876 BORN 1842 DIED 1911 BORN 1862 DIED 1935
Claimed to have been the first woman to The first American woman to gain a Had no education in chemistry, but
graduate as a chemist, in 1870. She was chemistry degree. Her work led to the carried out experiments in her kitchen
also the first woman to publish her own first water quality standards in America on the surface tension of water. Now
chemical research from a modern lab. and the first modern sewage plant. considered a pioneer of surface science.
LUCY EVEREST BOOLE MARGARET SEWARD ANNIE MALONE

BORN 1862 DIED 1904 BORN 1864 DIED 1929 BORN 1869 DIED 1957
The first woman to research pharmacy Tutored, researched, and lectured in Malone, a chemist and entrepreneur,
in England, and the first woman to co- chemistry. Carried out vital work on food developed hair care products for black
author a pharmaceutical research paper. nutrition during the First World War, and women. Her success made her the first
Also the first female fellow of the RSC. was later awarded an MBE for her work. African-American woman millionaire.
EDITH HUMPHREY MAUD MENTEN ELLEN GLEDITSCH

BORN 1875 DIED 1977 BORN 1879 DIED 1960 BORN 1879 DIED 1968
The first British woman to obtain a PhD Carried out key research in biochemistry. In her early career, Gleditsch worked
in chemistry. Carried out key research on In 1913, she co-devised the Michaelis- under Marie Curie. She established the
inorganic complexes, but was forced out Menten equation for study of the rate of half-life of radium and contributed to the
of a research career by sexist attitudes. enzyme-catalysed reactions. confirmation of the existence of isotopes.

Periodic graphics
More
online
To see more of
to compoundchem.
com. To see all of
MARCH 6, 2017 | CEN.ACS.ORG | C&EN 37

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With Compound Interest sale in the U.K. at
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CEN.ACS.ORG 38 OCTOBE R 1 2 , 20 1 5
CRIME SCENE CHEMISTRY - LUMINOL
What triggers luminol’s chemiluminescence?
O
NH
NH
BLOOD BLEACH FAECES URINE HORSERADISH
NH2 O The reaction that triggers luminol’s chemiluminescence has to be catalysed. The iron in blood can carry
out this role, but luminol can also be oxidised by bleach to achieve the same effect. Enzymes in faeces
and horseradish can also help trigger the reaction.
How luminol reacts to produce light

O O O
*
Base
NH O- O-
H2O2 + + Light
- -
NH Catalyst O O
NH2 O NH2 O NH2 O
Luminol solution also contains an oxidising agent, such as hydrogen peroxide, and a base. In the
presence of a catalyst, the reaction produces energy, promoting electrons in the product to higher
energy levels, before they fall back down and release their excess energy as light.

C Luminol image: Flickr.com,. Jack Spades, Creative Commons BY Licence.
BY NC ND
CRIME SCENE CHEMISTRY: FINGERPRINT DETECTION
Crime scene fingerprints sometimes require chemical techniques to make them visible. Here, we take a look at four key techniques used.
TYPES OF FINGERPRINT LATENT FINGERPRINT POWDERS CYANOACRYLATE FUMING
O
PIGMENTS C Al Zn Cu N
Includes aluminium, zinc, and copper powders, and colloidal carbon O
BINDERS ROSIN GUM AR ABIC
PATENT PRINT Wide variety used IRON POWDER LYCOPODIUM METHYL CYANOACRYLATE
The name given to finger

A range of powders of varying compositions, but Surfaces where latent fingerprints may be found can be
prints on hard surfaces which
commonly consisting of a pigment and a binder. When exposed to cyanoacrylate fumes to make them visible.
are visible. These can be
brushed on a surface, the powder clings to the moist and Cyanoacrylates are used in superglue, and polymerise on
photographed without the aid of
oily residue left by fingerprints, visualising them. contact with fingerprint residue, making a white 3D matrix.
chemicals to improve visibility.
LATENT PRINT
CHEMICAL DEVELOPERS VACUUM METAL DEPOSITION (VMD)
Fingerprints made by the body's O O –
O Print residue, including oils/fats.
oils and sweat remaining on
hard surfaces after contact. Not OH
N Au Gold deposits over entire surface;
it diffuses into any fat present.
visible, so various techniques are OH
used to make them visible.
O O O
PLASTIC PRINT Zn Zinc deposits on regions of gold

NINHYDRIN RUHEMANN'S PURPLE nuclei but not on fatty deposits.
Three-dimensional fingerprints
left on soft surfaces such as wax Ninhydrin is a commonly used chemical developer. It reacts This process involves layers of metal atoms being left on a
or wet paint. Already visible, so with amino acids in sweat, producing a purple compound. surface under vacuum conditions to visualise latent prints.
can be photographed without Other developers, such as 1,2-diazafluoren-9-one (DFO), The usual combination is gold followed by zinc. It works
the use of additional techniques. make fingerprints glow in certain colours of light. because the zinc doesn't deposit on fatty regions.

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives International 4.0 licence.
Fingerprint by Wilson Joseph, CC-BY licence: https://thenounproject.com/search/?q=fingeprint&i=36332 BY NC ND
A BRIEF HISTORY OF CHEMICAL SHARK REPELLENTS
1943-1974 1984-2000 1990-PRESENT
COPPER ACETATE, ‘SHARK CHASER’ SURFACTANTS: SLS & OTHERS SEMIOCHEMICAL REPELLENTS
O O O
O O HN HN
O
S Na+ O O
O-
H3C O- Cu2+ -O CH3 O
COPPER ACETATE SODIUM LAURYL SULFATE SUCCINIMIDES
Thought to repel sharks by mimicing Of a number of surfactant chemicals, Compounds exuded by the American
the presence of decomposing shark sodium lauryl sulfate, commonly found Crocodile were found in studies to
meat. It was combined in a ‘cake’ with a in toothpaste, was found to have some induce immobility in juvenile sharks in
black dye as the repellent named ‘shark repellent effect - but it needed to be at controlled trials. However, field trials of
chaser’, which was standard issue for US too high a concentration in the water to the particular compounds used in this
military personnel. meet the US navy’s criteria for a non- study have yet to be attempted.
directional shark repellent.
Researchers later determined that ‘shark
In other studies, an extract that was
chaser’ had no significant repellent
obtained from putrified shark carcasses
value, with the dye’s visual deterrent
has been noted to produce repellent
being falsely interpreted as a repellent
responses in several coastal shark
effect. Taken out of service in 1974.
species. Research is still ongoing.
N N
N NH © COMPOUND INTEREST 2014

n
WWW.COMPOUNDCHEM.COM
SHARED UNDER A CREATIVE COMMONS
AT TRIBUTION-NC-ND LICENCE
C
ANILINE BLACK DYE
THE CHEMISTRY OF LED LIGHTS
LED lights come in a full range of colours – this graphic takes a closer look at the chemistry behind how their light and varied hues are achieved.
RED ORANGE YELLOW GREEN BLUE VIOLET
GaAsP GaAsP GaAsP GaP InGaN InGaN
AlGaInP AlGaInP AlGaInP GaN AlGaN AlGaN
GaP GaP GaP InGaN ZnSe GaN
HOW DO LEDS WORK? HOW ARE DIFFERENT COLOURS MADE?

P-TYPE
Light emitting diodes (LEDs) use semiconducting

materials to produce light and colour. Many of the BLUE
GREEN
materials used are based on gallium, such as gallium ORANGE RED
POWER
phosphide (GaP) and gallium nitride (GaN).

LIGHT
Layers of the semiconductor are "doped" with
impurities. This creates an n-type layer, which has A variety of colours are made possible by the use of
electrons spare, and a p-type layer, which has different semiconducting materials, and "doping"
electron "holes". When a current is applied, electrons them with different types and amounts of impurities.
from the n-type layer combine with the "holes" in the This affects the energy gap between the n-type
p-type layer. When the electrons fall into these holes,
N-TYPE and p-type layers, affecting the wavelength of light
they release energy in the form of visible light. produced when a current passes through the LED.

PeriodicGraphics
CEN.ACS.ORG 30 JANUARY 1 2 , 20 1 5
CARBON DIOXIDE AND OCEAN ACIDIFICATION
Climate change is a much-discussed effect of rising carbon dioxide levels, but they can also affect our oceans. This graphic takes a look at how.
THE BASICS THE CHEMISTRY OF OCEAN ACIDIFICATION THE EFFECTS OF OCEAN ACIDIFICATION
AB S Atmospheric carbon dioxide dissolves in seawater (1) and reacts with 1 EFFECT ON CALCIFYING ORGANISMS AND CORAL
CO2 OR
B
ED
the water to form carbonic acid (2). Carbonic acid dissociates (splits
up) into its ions (3); hydrogen ions produced by this dissociation
increase acidity, lowering seawater pH. Increased atmospheric carbon
dioxide ultimately produces more hydrogen ions, lowering pH further.
pH 8.1 LESS CARBONATE DISSOLUTION
CaCO3 Ca2+ + CO32–

pH 7.7
pH INCREASED CARBONATE DISSOLUTION
ACIDITY CO2 ATMOSPHERIC CARBON DIOXIDE

As ocean pH drops, hydrogen ions react with carbonate ions.
Calcifying organisms such as clams, oysters and crustaceans use
the carbonate ions from seawater to make shells. When calcium
Atmospheric carbon dioxide has carbonate is undersaturated in seawater, their shells can start
increased by 40% from pre-industrial 1 HYDROGEN IONS + BICARBONATE IONS dissolving. Coral skeletons can also be affected.
levels due to burning of fossil fuels
and deforestation. Ocean acidification 2 3
occurs when atmospheric carbon
dioxide dissolves in seawater. CO2 + H2O H2CO3 H+ + HCO3– 2 EFFECT ON FOOD WEBS AND FISHING
PRE-
INDUSTRIAL 2013 2100 DISSOLVED CARBONIC 4 £$€
CARBON DIOXIDE ACID
Calcifying organisms are at the root of a number of marine food
pH pH pH webs. Negative effects on their population could have a knock-on
8.2 8.1 7.7 HYDROGEN IONS + CARBONATE IONS 2H+ + CO32– effect on species that feed on them, impacting fishing industries.
25% more acidic (Projected)
3 EFFECTS ON ANIMAL CHEMICAL SIGNALLING

Acidity and alkalinity are measured on Hydrogencarbonate ions can dissociate further to form carbonate ions
the logarithmic pH scale. A pH over 7 is
alkaline; below 7 is acidic. A change of
one unit represents a tenfold change
(4) but this is less favoured. Consequently hydrogencarbonate ions are
the most abundant form of inorganic carbon in the oceans. Calcium
carbonate can also react with dissolved carbon dioxide in seawater to
pH 8.1 Egg
Ventilation
(VS. CONTROL)
pH 7.7 Egg
Ventilation
(VS. CONTROL)
in acidity or alkalinity. Seawater is form more hydrogencarbonate ions (5).

Many marine species use chemical signals for detecting
alkaline, but average ocean surface pH predators, settlement, and reproduction. Ocean acidification can
has dropped by 0.1 since pre-industrial alter signalling molecules, which could in turn have potentially
times, a 25% increase in acidity. 5 CaCO3 + CO2 + H2O Ca2+ + 2HCO3– detrimental effects on a number of different species.

THE PERIODIC TABLE’S ENDANGERED ELEMENTS
1 2
H
HYDROGEN
LIMITED AVAILABILITY – FUTURE RISK TO SUPPLY Hehelium
3 4 5 6 7 8 9 10
Li Be RISING THREAT FROM INCREASED USE B C N O F Ne

Lithium BERYLLIUM Boron carbon NITROGEN oxygen fluorine neon
11 12 SERIOUS THREAT IN THE NEXT 100 YEARS 13 14 15 16 17 18
Na Mg Al Si P S Cl Ar
SODIUM MAGNESIUM Aluminium silicon PHOSPHORUS sulfur chlorine argon
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K
Potassium
Ca
calcium
Sc
Scandium
Ti
Titanium
V
vanadium
Cr
chromium
Mn
manganese
Feiron
Co
cobalt
Ni
Nickel
CuCopper
Zn zinc
Ga
Gallium
Ge
germanium
As
arsenic
Se
selenium
Br
bromine
Kr
krypton
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb
RUBIDIUM
Sr
Strontium
Y
yttrium
Zr
ziRconium
Nb
NIOBIUM
Mo
molybdenum
Tc
Technetium
Ru
ruthenium
Rh
Rhodium
Pd
Palladium
Ag
SILVER
Cd
Cadmium
In
Indium
Sn Tin
Sb
antimony
Te
tellurium
I
iodine
Xexenon
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs
CAESIUM
Ba
Barium
E57-71 Hf
Hafnium
Ta
tantalum
W
Tungsten
Re
Rhenium
Os
osmium
Ir
iridium
Pt
Platinum
Au gold
Hg
Mercury
Tl
Thallium
Pblead
Bi
Bismuth
Po
polonium
At
astatine
Rnradon
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra E89-103 Rf Db Sg Bh Hs Mt Ds Rg Cn Uut Fl Uup Lv Uus Uuo

FRANCIUM RADIUM Rutherfordium dubnium seaborgium bohrium hassium meitnerium Darmstadtium ROENTGENIUM copernicum Ununtrium flerovium ununpentium Livermorium ununseptium ununoctium
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
lanthanum Cerium praseodymium Neodymium prometheum samarium europium gadolinium terbium Dysprosium holmium erbium thulium Ytterbium Lutetium
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
Ac
actinium
Th
thorium
Pa
protactinium
U
uranium
Np Pu
plutonium
Am
americium
Cm curium
Bk
berkelium
Cf
californium
Es
einsteinium
Fm
fermium
Md
mendelevium
No
nobelium
Lr
Lawrencium
neptunium
SOURCE: CHEMISTRY INNOVATION KNOWLEDGE TRANSFER NETWORK
Produced for the ACS Green Chemistry Institute by Andy Brunning/Compound Interest.
Ci Shared under a Creative Commons BY-NC-ND 4.0 International license. BY NC ND
THE CHEMISTRY OF PETROL & DIESEL
There's a lot behind the fuel we put in our cars – in this graphic, we take a look at the differences between diesel, leaded petrol, and unleaded petrol.
PETROL & DIESEL – THE DIFFERENCE OCTANE RATINGS & KNOCKING
PETROL
35–200 ˚C 5–12 CARBONS
33.7 MJ
PER LITRE
DIESEL
250–300 ˚C 10–15 CARBONS
36.9 MJ
PER LITRE
n-HEPTANE ISOOCTANE
OCTANE RATING: 0 OCTANE RATING: 100
Petrol and diesel are both obtained by fractional Knocking occurs when fuel's combustion doesn't
distillation of crude oil. However, they differ in their LEADED UNLEADED DIESEL
occur in sync with the engine cycle. This causes lower
composition. Diesel is a fraction of crude oil that engine efficiency and engine damage. Octane ratings
is removed at a higher boiling point, and contains gauge how well fuel avoids this problem, with higher
a larger amount of energy per litre, meaning more values indicating less knocking. Isooctane (100) and
miles can be covered with the same volume of fuel. n-heptane (0) are used as references.
Sorry
out of
use
HOW ENGINES WORK LEADED & UNLEADED PETROL
1 INTAKE AIR, FUEL INJECTED (PETROL ENGINES)
2 COMPRESSION HIGHER COMPRESSION WITH DIESEL Pb

3 COMBUSTION FUEL INJECTED (DIESEL ENGINES) OCH3
4 EXHAUST WASTE GASES FROM COMBUSTION
TETRAETHYL LEAD MTBE BENZENE
SPARK PLUG FUEL IN
(petrol engine only) (diesel)
AIR IN
Compounds can be added to petrol to boost its
FUEL IN
(petrol only) octane rating. Tetraethyl lead was one of these, but
is now banned in most countries as it releases toxic
lead fumes. Alternative anti-knocking agents used in
unleaded petrol include methyl tertiary-butyl ether
(MTBE), ethanol, benzene, and toluene.
1 2 3 4

RECYCLING RATES OF SMARTPHONE METALS
COLOUR KEY: < 1% RECYCLE RATE 1–10% RECYCLE RATE 10–25% RECYCLE RATE 25–50% RECYCLE RATE > 50% RECYCLE RATE NON-METAL (OR RECYCLE RATE UNKNOWN)
SCREEN ELECTRONICS
49
49
TOUCH: INDIUM TIN OXIDE WIRING & MICROELECTRONICS 29 47
In
Indium 8 Used in a transparent film over Copper is used for wiring, and for Cu
COPPER
Ag
Indium 8 SILVER
O the phone’s screen that conducts micro-electrical components along

50
OXYGEN
Oxygen
electricity. This allows the screen to with gold and silver. Tantalum is 79 73
function as a touch screen. This is the major component in micro-
Sn TIN the major use of indium. capacitors.
AuGOLD
Ta
TANTALUM
66
13 14
GLASS: ALUMINA & SILICA MICROPHONES & VIBRATIONS 28 59
Al
Aluminium
Si
SILICON On most phones the glass is Nickel is used in the microphone Ni
NICKEL
Dy Pr
PRASEODYMIUM
DYSPROSIUM
aluminosilicate glass, a mix of and for electrical connections.
aluminium oxide & silicon dioxide. Rare earth element alloys are used
It also contains potassium ions
8 19 65 60 64
in magnets in the speaker and
O
OXYGEN
K
POTASSIUM which help strengthen it. microphone, and the vibration unit. Tb
TERBIUM
Nd
NEODYMIUM
Gd GADOLINIUM
39 57 65
COLOURS: RARE EARTH METALS THE SILICON CHIP 14 8 51
Y La Tb Pure silicon is used to manufacture Si O Sb

Yttrium LANTHANUM TERBIUM A variety of rare earth metal- SILICON OXYGEN ANTIMONY
containing compounds are used the chip, which is then oxidised to

to help to produce the colours in produce non-conducting regions.
Other elements are added to allow
33 15 31
59 65 66
Pr Eu Dy a smartphone’s screen. Some of

the chip to conduct electricity.
As P Ga
PRASEODYMIUM Europium DYSPROSIUM these compounds are also used ARSENIC PHOSPHORUS GALLIUM
to help reduce light penetration

64
into the phone. Many of the ‘rare
Gd earths’ occur commonly in the CONNECTING ELECTRONICS 50 82
GADOLINIUM Earth’s crust, but often at levels too Tin & lead were used in older Sn Pb
low to be economically extracted. solders; newer, lead-free solders
TIN LEAD
use a mix of tin, copper & silver.
BATTERY CASING
Magnesium alloy is used to make some phone
3 27
Most phones use lithium ion batteries, composed
6 12
Li
LITHIUM
CoCOBALT of lithium cobalt oxide as a positive electrode cases, whilst many others are made of plastics, C Mg
8 CARBON
which are carbon-based. Plastics will also include
MAGNESIUM
O and graphite (carbon) as the negative electrode.

6 13
OXYGEN
Sometimes other metals, such as manganese, are flame retardant compounds, some of which contain
used in place of cobalt. The battery casing is often bromine, whilst nickel can be included to reduce
35 28
C Al electromagnetic interference. Br Ni
CARBON ALUMINIUM
made of aluminium. BROMINE NICKEL

The 12 Principles of
GREEN CHEMISTRY
Green chemistry is an approach to chemistry that aims to maximize efficiency and minimize hazardous effects on human
health and the environment. While no reaction can be perfectly ‘green’, the overall negative impact of chemistry research
and the chemical industry can be reduced by implementing the 12 Principles of Green Chemistry wherever possible.
1. WASTE PREVENTION 7. USE OF RENEWABLE FEEDSTOCKS

Prioritize the prevention of waste, Use chemicals which are made from
rather than cleaning up and treating renewable (i.e. plant-based) sources,
waste after it has been created. rather than other, equivalent
Plan ahead to minimize waste at chemicals originating from
every step. petrochemical sources.
2. ATOM ECONOMY 8. REDUCE DERIVATIVES

Reduce waste at the molecular Minimize the use of temporary
level by maximizing the number of derivatives such as protecting
atoms from all reagents that are groups. Avoid derivatives to reduce
incorporated into the final product. reaction steps, resources required,
Use atom economy to evaluate and waste created.
reaction efficiency.
3. LESS HAZARDOUS CHEMICAL SYNTHESIS 9. CATALYSIS

Design chemical reactions and Use catalytic instead of
synthetic routes to be as safe as stoichiometric reagents in reactions.
Choose catalysts to help increase
! possible. Consider the hazards of
all substances handled during the selectivity, minimize waste, and
reaction, including waste. reduce reaction times and energy
demands.
4. DESIGNING SAFER CHEMICALS 10. DESIGN FOR DEGRADATION

Minimize toxicity directly by Design chemicals that degrade and
molecular design. Predict can be discarded easily. Ensure
and evaluate aspects such as that both chemicals and their
physical properties, toxicity, and degradation products are not toxic,
environmental fate throughout the bioaccumulative, or environmentally
design process. persistent.
5. SAFER SOLVENTS & AUXILIARIES 11. REAL-TIME POLLUTION PREVENTION

Choose the safest solvent available Monitor chemical reactions in
for any given step. Minimize the real-time as they occur to prevent
total amount of solvents and the formation and release of any
auxiliary substances used, as these potentially hazardous and polluting
make up a large percentage of the substances.
total waste created.
6. DESIGN FOR ENERGY EFFICIENCY 12. SAFER CHEMISTRY FOR ACCIDENT PREVENTION
Choose the least energy-intensive Choose and develop chemical
chemical route. Avoid heating and procedures that are safer and
cooling, as well as pressurized and inherently minimize the risk of
vacuum conditions (i.e. ambient accidents. Know the possible risks
temperature & pressure are optimal). and assess them beforehand.
© COMPOUND INTEREST 2015; WWW.COMPOUNDCHEM.COM

C Shared under a CC Attribution-NonCommercial-NoDerivatives licence. BY NC ND
THE CHEMISTRY OF BIODEGRADABLE PLASTICS
COMMON BIOPOLYMERS & SOURCES EVERYDAY USES OF BIOPOLYMERS ADVANTAGES AND DISADVANTAGES
POLYLACTIC ACID (PLA) GLOBAL PLASTIC PRODUCTION

CONVENTIONAL BIODEGRADABLE &
Biodegradable coffee cups are PLASTICS BIOPLASTICS
O paper cups with a PLA lining to

make the paper waterproof.
333 2.11
million tonnes million tonnes
O n
Use of bioplastics is increasing, but they still account for

Obtained from fermented plant starch from corn, less than 1% of the global plastics market (as of 2018).
cassava, sugar cane or sugar beet.
PLA has the second largest
production volume of any
CONDITIONS FOR BIODEGRADING
POLYHYDROXYALKANOATES (PHAs) biopolymer (behind TPS). It
is also used in plastic films,
CH3 O bottles, and food containers.
O2
H
O OH MOISTURE OXYGEN MICROORGANISMS pH TEMPERATURE
n poly-(R)-3-hydroxybutyrate (P3HB)
Compostable plastics need specific conditions to break

Extracted from bacteria, which produce it via the PLA and TPS both find use down – and take much longer to do so completely if they
fermentation of sugar or lipids. in the manufacture of plastic go to landfill instead of being recycled. However, they still
cutlery that’s biodegradable. break down faster than conventional plastics.
THERMOPLASTIC STARCHES (TPS)

CH2OH CH2OH CH2OH
CO 2
OH
O
OH
O
OH
O CH4
TPS is also used in food waste
O O OH
OH bags and some magazine
OH OH 300–600
OH
wrappers. PHAs have fewer Biodegradable plastics are more expensive than plastics
uses, but have medical uses derived from fossil fuels on weight basis, and require
Starches from plant materials are heated with water, such as in surgical sutures. land to grow raw materials. However, the greenhouse gas
then mixed with plasticisers or other polymers. emissions associated with their production are lower.

Ci This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 licence. BY NC ND
HOW DID AMMONITE FOSSILS FORM?
HOW AMMONITE FOSSILS FORM FOSSILISATION AND MINERALS
Dead ammonites were buried by sediment Over time the chambers of the buried
millions of years ago. Chemical processes ammonite shell can fill with mineral
then eventually produced a fossil. deposits. This produces detailed fossils
and some shell can remain intact. In other
cases the shell dissolves and mineral
deposits fill the cavity to produce a cast.
SILICIFICATION PYRITIZATION
AMMONITE SHELLS SiO2 FeS2

Ammonite shells are made of the calcium
Silica Iron sulfide
carbonate mineral aragonite. Over long
time periods the aragonite can change
Grey/black Golden
into a more stable mineral form of calcium appearance appearance
carbonate, called calcite.
Calcium carbonate Calcium carbonate
Calcium carbonate
In silicification, silica-rich solutions replace
CaCO3 calcium carbonate with silica. Pyritisation
occurs in sediment saturated with iron
sulfides. Pyritised fossils can oxidise and
Aragonite Calcite slowly disintegrate in humid conditions.

WATER TREATMENT – FROM RESERVOIR TO HOME
We take the water coming from our taps for granted – but what happens to it before it gets there? Here’s how chemistry helps!
Al2(SO4)3
FeCl3
CARBON
RAW WATER SCREENING COAGULANTS ADDED SEDIMENTATION
Water is drawn Screening helps to remove large Coagulants such as aluminium Under slow mixing, the clumped
from lakes, rivers, matter from the water, such as sulfate and ferric chloride are mixed particles increase in size, a process
or reservoirs, or leaves and rubbish, using a wire into the water. These make particles called flocculation. Most of them SAND
can be drawn from mesh. This prevents the debris from of dirt and dissolved substances in sink to the bottom and form a
groundwater using causing obstructions within the the water clump together so that sludge, which can be removed from
boreholes. facility, making treatment easier. they can be removed. the water, treated and disposed of.
GRAVEL
O
Cl Cl HO P OH CaCO3
OH
TO HOMES CHLORINATION ANTI-CORROSION AGENTS pH CORRECTION FILTRATION
Residual chlorine in Chlorine is added to water to kill Agents such as orthophosphates can Water that is too acidic can lead Some particles remain in the
the water safeguards bacteria and viruses, preventing be added to the water, particularly in to water pipe corrosion. It can be water after sedimentation; these
against pathogens. water-borne diseases like cholera areas with lead pipes. These agents passed through a filter containing are removed by filtration through
Fluoride can be added
and typhoid. Ozone can be used form lead-phosphate complexes on crushed limestone (mainly calcium coal, sand, and gravel beds. They
after chlorination to
help to prevent tooth instead of chlorine, and avoids the inside of the pipes, stopping lead carbonate) to raise pH. Acids can be are cleaned by pumping air and
decay. disinfection byproducts. getting into the water. added if the pH is too high. water backwards through them.

EVERYDAY COMPOUNDS: SALICYLIC ACID
SALICYLIC ACID IS FOUND NATURALLY IN MANY PLANTS, & CAN BE ISOLATED FROM WILLOW TREE BARK. UNRIPE FRUITS & VEGETABLES ARE NATURAL SOURCES OF SALICYLIC ACID.
AS A KERATOLYTIC AGENT AS AN ANTI-DANDRUFF AGENT

O
Salicylic acid is present in acne creams As a keratolytic agent, salicylic acid is
& wart treatment as a keratolytic also found in anti-dandruff shampoos.
agent; it softens keratin, the proteins OH
It helps loosen dry skin on the scalp
that make up the outer layer of skin, and remove dry skin flakes.
by increasing the amount of moisture
in the skin, and assists the exfoliation OH Most of the anti-dandruff shampoos
of skin cells. that use it will contain around 2-3%
salicylic acid.
SALICYLIC ACID
AS AN ANTIBACTERIAL AGENT 2-Hydroxybenzoic acid AS A PRECURSOR MOLECULE
O White, crystalline solid
O OH
C7H6O3
Na+
O- O
ACNE CREAM
OH O
SHAMPOO
SODIUM SALICYLATE ASPIRIN (ACETYL SALICYLIC ACID)
Sodium salicylate is the sodium salt Salicyclic acid is reacted with acetic
of salicylic acid, and has antibacterial anhydride, using sulfuric acid or
properties. It is for this reason that phosphoric acid as a catalyst, to produce
TOOTHPASTE
it can be found in some toothpastes aspirin. Aspirin has analgesic and anti-
MEDICINE
& mouthwashes. Sodium salicylate is inflammatory properties. It is one of the

also used, along with salicylic acid, as a most widely used medications in the
food preservative due to its antiseptic world, with around 40,000 tonnes of it
properties. being consumed each year.

EVERYDAY CHEMICALS: ALUMINIUM CHLORHYDRATE
Aluminium chlorohydrate is an inorganic polymer, with the general formula AlnCl3n-m(OH)m. It is synthetically produced from other aluminium compounds,
and is a common active ingredient in anti-perspirants, along with other aluminium-containing compounds. It also finds applications in water treatment.
ANTIPERSPIRANTS SAFETY
PORE
EPIDERMIS
OH OH Amount of aluminium
DERMIS
HO Al Al OH
0.012% absorbed through the skin
from antiperspirants
SWEAT GLAND
Cl OH
Aluminium chlorohydrate is the active ingredient in many There is no scientific evidence that aluminium
anti-perspirants, used at a concentration of 10-25%. compounds in anti-perspirants can cause cancer, despite
The exact manner in which it helps prevent perspiration claims to the contrary. Research shows that only 0.012%
has been debated, but it is now generally accepted that of aluminium contained in anti-perspirants is absorbed
it forms a gelatinous aluminium hydroxide-protein gel, ALUMINIUM CHLOROHYDRATE through the skin. This is less than would be expected to
which acts to obstrut the sweat glands. be absorbed from food during the same time.
White powder
OTHER ALTERNATIVES Al2Cl(OH)5 WATER & WASTE MANAGEMENT
Al3+ Zr4+
ALUMINIUM AND ZIRCONIUM
COMPLEXES Flocculation
A range of similar aluminium-containing compounds Aluminium chlorohydrate is also commonly used

can also be found in antiperspirants, and act to prevent in water and waste management processes to help
perspiration in a similar manner. Generally, they are remove dissolved organic matter and small particles of
either types of aluminium chlorohydrates, or aluminium WATER
TREATMENT impurities. It acts as what is known as a ‘flocculating
zirconium chlorohydrates. Aluminium zirconium agent’, causing particles to lump together so they can
chlorohydrates are thought to be more effective. then be removed from water.

C Graphic shared under a CC Attribution-NonCommercial-NoDerivatives licence. Glowstick photo: Jonathan Stonehouse, CC-BY, https://goo.gl/3nKp8F BY NC ND
EVERYDAY CHEMICALS: SODIUM LAURYL SULFATE
Sodium lauryl sulfate (also known as sodium dodecyl sulfate, or more simply abbreviated to SLS) is a surfactant chemical found in many cleaning
and hygiene products, including toothpaste, shampoo, shaving cream and bubble baths. These, along with several other uses, are detailed below.
IN SHAMPOOS IN TOOTHPASTES
HYDROPHILIC (WATER-LOVING) O O
PART OF SURFACTANT MOLECULE
H3C O S -
Na+
OIL O O O O
+ n
HYDROPHOBIC (WATER-HATING) H3C S Na
PART OF MOLECULE O O-
10 SODIUM LAURETH SULFATE
(a common SLS alternative)
Sodium lauryl sulfate (SLS) is a surfactant, meaning SLS is added to toothpaste as a foaming agent; it also
the molecule contains a water-soluble portion and a interacts with taste receptors in the mouth. It suppresses
water-insoluble portion. It attaches to oil and grease, sweet receptors and breaks down phospholipids that act
suspending them in water and allowing them to be as inhibitors on bitter receptors. Drinking orange juice
removed. It also lowers the surface tension of water, SODIUM LAURYL SULFATE after brushing your teeth tastes bad, as SLS dulls the
acting as a foaming agent and allowing bubbles to form. sweet taste and promotes the bitter.
White powder
IN ENGINE DEGREASERS CH3(CH2)11OSO3Na AS A POTENTIAL SHARK REPELLENT
O O
O O HN HN
H3C S -
Na+ O CH3 O CH3
O O
10
H3C H3C
HYDROPHOBIC HYDROPHILIC
SEMIOCHEMICALS SHOWN TO HAVE SHARK-REPELLING PROPERTIES
Sodium lauryl sulfate is found in some engine A 2001 study confirmed that sodium lauryl sulfate
degreasers, where it acts in a similar capacity to remove acts as a shark repellent, as a result of its hydrophobic
grease. Generally it’s present at a higher concentration in properties. Despite this, it does not meet the required
these cleaners than it is usually found at in shampoo. It’s criteria for use as a non-directional, cloud-based
also used in industry as a leather-softening agent, wool- repellent. Semiochemicals and rare earth metal magnets
cleaning agent, and as a floor cleaner. have both been suggested as better alternatives.

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 licence. BY NC ND
E VERY DAY COMPOUNDS: GLYCEROL
ALSO KNOWN AS GLYCERIN, GLYCEROL IS PRODUCED AS A BY-PRODUCT OF SOAP-MAKING, & CAN ALSO BE PRODUCED SYNTHETICALLY
IN THE FOOD INDUSTRY IN PERSONAL CARE PRODUCTS

There are a number of different uses Glycerol is used as a method of
for glycerol in the food industry. OH improving smoothness in toothpaste,
It can be used as a sweetener in skin care products, shaving cream,
drinks, as an important moistening HO OH soaps, and hair-care products. It
agent for baked goods, and is also serves as an emollient and lubricant
added to confectionary to prevent in these products. It is also found in
sugar crystallisation. Additionally, it pharmaceuticals, where it is commonly
is often used as a solvent for food used as a humectant to stop creams
colourings, and higher levels can have drying out, and as a tablet-holding
a preservative effect. GLYCEROL agent.
Propane-1,2,3-triol
Colourless, odourless,
IN ANTI-FREEZE viscous liquid
AS A PRECURSOR TO EXPLOSIVES
C3H8O3
Glycerol was historically used as an Glycerol can be reacted with a mixture
anti-freeze, since it can form strong of sulfuric acid & nitric acid to produce
hydrogen bonds with water, lowering nitroglycerin, an explosive liquid
the freezing point. It was succeeded SOAP commonly used in dynamite and other
by ethylene glycol (shown below), but propellants. This compound is also
as this is toxic to humans, glycerol is used as a medication for ischemic heart
being reconsidered as an non-toxic disease. O
alternative. N+
O O-
HO -
O O O O-
+ +
N N
OH ANTI O O
FREEZE
ETHYLENE GLYCOL NITROGLYCERIN
C © COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM

BY NC ND
EVERYDAY COMPOUNDS: SODIUM HYPOCHLORITE
A SOLID COMPOUND WHICH, WHEN DISSOLVED IN WATER, IS COMMONLY KNOWN AS BLEACH. FREQUENTLY USED AS A DISINFECTANT.
IN BLEACH IN SWIMMING POOLS

70% of sodium hypochlorite produced Chlorinated swimming pool water
is used to make bleach, which consists isn’t chlorinated with chlorine, which
O
of around 3-8% sodium hypochlorite; is difficult to handle. Instead, sodium
sodium hydroxide is often also present Na+ hypochlorite is used. In water it forms
to prevent the sodium hypochlorite Cl the disinfectant hypochlorous acid.
decomposing. When it’s dissolved in Calcium hypochlorite is an alternative.
water, hypochlorous acid (HOCl) is
formed, a very strong oxidising agent The uric acid in urine can react with
that can react with and break down hypochlorous acid to produce toxic
many molecules, including dyes. SODIUM HYPOCHLORITE cyanogen chloride, though not in high
Antiformin, bleach enough levels to be harmful to health.
Bleach shouldn’t be mixed with other White powder
O
cleaners, as reaction with acids can Green/yellow solution in water
produce toxic chlorine gas: NaClO H
N
HN URIC
O ACID
HClO + HCl Cl2 + H2O O N
N
H
H
BLEACH
IN ANTIBACTERIAL SPRAYS
NERVE AGENT NEUTRALISATION
Solutions containing around 0.5%
Sodium hypochlorite is used in a 50% sodium hypochlorite can be used as
solution for blister and nerve agent disinfectants effective against a wide
decontamination, and works via its range of bacteria. The hypochlorous
oxidising action. It’s also used in a 0.5% acid attacks the proteins in the cells
solution to reduce tissue damage to of microbes, and also causes their cell
blister agent victims. membranes to burst.
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BY NC ND
EVERYDAY CHEMICALS: HYDROGEN PEROXIDE
Hydrogen peroxide is a colourless liquid that resembles water; in fact, its chemical formula is very similar to that of water, but it contains an extra oxygen
atom. It is a strong oxidiser, and is commonly used as a bleaching agent & disinfectant. It’s also one of the compounds that helps make glow sticks glow.
BLEACHING PAPER & STAINS IN HAIR DYES
H NH2
O O- H
PERHYDROXYL ION O O H2N
Primary oxidising species
H PARAPHENYLENEDIAMINE
Around half of the two million tons of hydrogen peroxide Hydrogen peroxide is used in hair dyes as an oxidiser,
produced each year is used to bleach paper. In homes, oxidising the natural melanin pigments in hair and
it’s found in some bleaches as an alternative to chlorine causing them to lose their colour. It also aids the dyeing
bleaches. It’s also used in some stain remover sprays as process by oxidising other chemicals in the dye mixture,
a bleaching agent, as it destroys the parts of chemical HYDROGEN PEROXIDE such as paraphenylenediamine (PPD), to help produce
structures, called chromophores, that cause colouration. the dye molecules that then colour the hair.
Colourless liquid
DISINFECTING WOUNDS H2O2 IN GLOW STICKS
O O
H OH
O O
O + O O 2 +
2H2O2 2H2O + O2 O
H O
O
O
O
DECOMPOSITION OF + Dye 2CO2 + Excited Dye
O
HYDROGEN PEROXIDE O
GLOWSTICK REACTIONS
Hydrogen peroxide is sometimes used as a disinfectant Hydrogen peroxide is included in a compartment of glow
for cuts, though its efficacy is debated. When it comes sticks. An ester compound is in the other compartment.
into contact with blood, it foams. This isn’t due to any When the glow stick is snapped, the hydrogen peroxide
kind of cleaning or disinfectant action, but because an and the ester compound react, and the product of this
enzyme in blood catalyses the breakdown of hydrogen reaction then decomposes, produces energy that excites
peroxide into water and oxygen gas. dye molecules and leads to emitted light.

C Graphic shared under a CC Attribution-NonCommercial-NoDerivatives licence. Glowstick photo: Jonathan Stonehouse, CC-BY, https://goo.gl/3nKp8F BY NC ND
EVERYDAY CHEMICALS: ACETIC ACID
Acetic acid, also referred to as ‘ethanoic acid’, is well known as the acidic component of vinegar. However, it also has a range of applications, particularly as
a precursor to a number of other important substances, outside of its normal household use. Here, we take a look at some of these common applications.
IN VINEGAR & FOOD MAKING GLUE & OTHER CHEMICALS

O O O
OH + O2 + H2O
OH
OXIDATION OF ETHANOL H3C OH O
(in presence of bacterial enzymes) VINYL ACETATE
Acetic acid is best known for its presence in vinegar, Approximately one third of all acetic acid is used in
produced by fermentation & oxidation of ethanol. Table the production of vinyl acetate. Polymerisation of vinyl
vinegar is a solution of 4-8% acetic acid in water. Trace acetate monomer produces the polymer polyvinyl
molecules contribute colour and nuances of flavour to acetate (PVA), the main component in PVA glue. Acetic
different types of vinegars. Acetic acid is also used in ACETIC ACID acid is also used as a solvent, and as a precursor to
foods as an acidity regulator, with the E number E260. photographic film, inks & dyes, and synthetic fibres.
Colourless liquid
AS A HOUSEHOLD CLEANER CH3COOH VINEGAR & BICARBONATE VOLCANO
O O O O
2 + CaCO3 Ca2+ + H2CO3 + NaHCO3 + CO2 + H2O
-
OH O OH O Na
2
REACTION OF ACETIC ACID WITH LIMESCALE REACTION OF ACETIC ACID WITH SODIUM BICARBONATE
Vinegar is often recommended as a household cleaner, Acetic acid in the form of vinegar can also be used in
for removing smears and streaks from windows and a common household science experiment. It can be
mirrors. It’s found in some descalers for removing reacted with baking powder (sodium bicarbonate) to
limescale, as it reacts with the calcium carbonate that produce a volcano-like effect. The acid reacts with the
limescale is primarily composed of. Studies have also bicarbonate in a neutralisation reaction, which also
shown acetic acid to have a good antibacterial effect. produces carbon dioxide, causing a frothing effect.

C Shared under a CC Attribution-NonCommercial-NoDerivatives licence. Vinegar volcano photo: Kate Ter Haar, CC-BY, https://goo.gl/u17tJb BY NC ND
EVERYDAY CHEMICALS: PIPERINE
Piperine is an alkaloid most commonly known for its presence in black pepper. However, it has some other surprising uses. Here, we document a selection.
IN BLACK PEPPER MEDICAL EFFECTS

O O
O O N
N
O N
O O
O O
O
N
PIPERINE CHAVICINE O
O
Alkaloid in pepper Isomer of piperine ANTIEPILEPSINE
Also known as ilepcimide
Piperine is 3-9% of black pepper. Black pepper’s ‘hot’ Black pepper was traditionally used as a remedy for
taste is due to piperine; it acts like capsaicin, the constipation and diarrhoea due to its piperine content.
compound in chilli peppers that causes their spiciness, It increases bioavailability of some medications, and also
though it is only 1% as hot. It triggers tongue nerves has some analgesic, anti-inflammatory, anti-mutagenic
which cause the sensation of heat. Piperine can irritate PIPERINE and anti-tumour properties. A piperine analogue,
nerve endings in the nose, causing sneezing. antiepilepserine, can be used in epilepsy treatment.
Yellow powder
AS AN INSECTICIDE C17H19NO3 IN FOODS & DRINKS
H
O N R
N S O
O2
O
PIPERINE-BASED PHENYLSULFONYLHYDRAZONE ACROLEIN
R = various phenyl-containing groups Formed during distillation of some spirits
Piperine can be used as a repellent against animals, Piperine is added to brandy in small amounts as a
and combined with other compounds can be used flavouring additive, in order to impart a pungent taste.
in insecticides against flies, lice and various other Some of the peppery flavour, however, comes from small
pests. Derivative compounds, such as piperine-based amounts of acrolein which can form during distillation.
phenylsulfonylhydrazones, can also show potent Piperine is also found in trace amounts in several foods,
delayed insecticidal activity. including cheese, sugar, and several meats.
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THE CHEMISTRY OF SPIDERWEBS
October is mating season for some spiders. Like them or loathe them, these arachnids use some
fascinating biochemistry to spin webs with unique material properties that scientists want to emulate.
SPIDER SILK'S ELASTICITY AND STRENGTH
HOYOH
NH 2
ALANINE GLYCINE SERINE
Spider silk is a protein fiber. Major amino acids in the silk proteins are
alanine and glycine. Serine and praline are also present in significant
quantities in some types of silk. Glycine-rich regions give spider silk
its elasticity, forming amorphous areas in its structure. Alanine-rich
regions link together through hydrogen bonds to form crystalline
areas that give spider silk its strength .
EUROPEAN GARDEN SPIDER SILK VS. KEVLAR SYNTHETIC SPIDER SILK
KEVLAR
Materials scientists want to find a way to reproduce spider silk's strength
and stretchiness. So far their attempts have been met with mixed
success; they've yet to produce synthetic spider silk on a large scale.
27°/o 270°/o 2.7°/o ~98°/o

ELASTICITY ELASTICITY ELASTICITY
(% increase in length
when stretched)
when stretched)
when stretched) 20/~ TER
1.1
STRENGTH
o.s
STRENGTH
3.6
STRENGTH
SILICA AND
CELLULOSE
(GPa) (GPa) (GPa)
180
TOUGHNESS
150
TOUGHNESS
so
TOUGHNESS
Some research has
used bacteria to
produce spider-silk-
like proteins.
In the U.S.. goats were
genetically modified
to produce spider silk
proteins in their milk.
U.K. researchers made
artificial spider silk with
silica- and cellulose-
based fibers.
(MJ•m- 3 ) (MJ• m-3 ) (MJ• m-3 )
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THE CHEMISTRY OF A CHILLI
C APSAICINOIDS
CAPSAICIN
OH
H
N
OCH3
O
DIHYDROCAPSAICIN
OH
H
N
OCH3
O T H E S C O V I L L E H E AT I N D E X
The spiciness of chillis is due to the presence of
compounds called capsaicinoids. The two
compounds above are the main capsaicinoids
in chilli peppers. They cause a burning
sensation when they come into contact with
mucous membranes, due to their interaction with JALAPEÑO CAYENNE PEPPER HABANERO GHOST PEPPER PEPPER SPRAY PURE CAPSAICIN
pain and heat sensing neurons. 8,000 50,000 350,000 1,400,000 5,300,000 16,000,000
Capsaicin is also used in some brands of pepper The Scoville scale is a taste detection based method for rating the heat of chil-
spray, and studies have shown it may be li peppers. A measured amount of pepper extract has sugar added to it incre-
capable of killing prostate and lung cancer cells. It mentally until the heat is undetectable through taste. Though it is an impre-
is toxic in large quantities. cise method, it has been estimated that 1 unit corresponds to 18µM.

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THE SIX POLYMORPHS OF CHOCOLATE
The molecules in cocoa butter can be stacked together in different ways - these are
known as ‘polymorphs’. Tempering chocolate is required to obtain only form V, the most
desirable. This is achieved by allowing the chocolate to cool at room temperature, which
leads to some of all the polymorphs except VI forming, then heating gently to just below
the melting point of form V, so it is the major form remaining.
FORM & MELTING

FORM & MELTINGPOINT
POINT DESCRIPTION
DESCRIPTION &
& PROPERTIES
PROPERTIES
BOTH SOFT AND CRUMBLY WITH
17.3˚C
NOTICEABLE BLOOMING
I Form I is produced by cooling melted
INCREASED STABILIT Y & DENSIT Y

chocolate rapidly (e.g. by putting it in the
freezer).
Form II is produced by cooling melted
23.3˚C
chocolate at 2˚C per minute. Form I crystals
II also gradually become Form II after a short

time of freezing temperature storage.
BOTH FIRM, BUT DON’T GIVE A GOOD
III 25.5˚C
‘SNAP’, AND SHOW SOME BLOOMING
Form III is produced by cooling at 5-10˚C.

Form II becomes Form III after storage at
low temperatures above freezing.
Form IV is produced by allowing melted
IV 27.3˚C
chocolate to cool at room temperature;
Form III also becomes Form IV after storage
at room temperature for some time.
SHINY, SMOOTH TEXTURE, GOOD
33.8˚C
‘SNAP’, AND MELTS IN THE MOUTH
V Formed by tempering chocolate slowly at
room temperature. Most desirable!
HARD AND MELTS SLOWLY IN THE
VI 36.3˚C
MOUTH, SHOWS SOME BLOOMING
Can’t be formed from melted chocolate -
can only be formed after solid, tempered
chocolate has rested for at least 4 months.

BY NC ND
T HE C HE MIS T R Y OF C HO C OL AT E
IS CHOCOLATE AN APHRODISIAC?
NH2
PHENYLETHYLAMINE
Phenylethylamine occurs naturally in the brain,

and is often referred to as ‘the love drug’ due
to its ability to produce feelings of well-being
and contentment. It is also present in significant
concentrations in chocolate, but since it is broken
down after ingestion, it has been ruled out as
causing a significant aphrodisiac effect. WHY IS CHOCOLATE TOXIC TO DOGS?
Tryptophan is a chemical in the brain linked to
the production of serotonin, the neurotransmitter O Theobromine is a mild stimulant, similar in
effect to caffeine, found in chocolate. This
that produces feelings of elation. It is present in
compound is harmless to humans at the levels
chocolate, but only in small quantities, and it is
N found in chocolate - a fatal dose would require
unlikely that it causes any aphrodisiac effect. HN eating tens of kilograms of milk chocolate!
O In cats & dogs, theobromine has a much

TRYPTOPHAN O N N more potent effect; small doses can lead to
OH vomiting & diarrhoea, whilst as little as 50g
of dark chocolate could kill a small dog.
HN NH2 THEOBROMINE

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MAJOR ORGANIC COMPOUNDS IN HERBS & SPICES
The herbs and spices used regularly in cooking are all a complex mix of organic compounds. This poster highlights some of the main organic
compounds found in each herb and spice that contribute to their flavour, aroma, or colour.
THYME ROSEMARY SAGE O R EG A N O O

M A RJ R A M
HO
OH
OH
sa
te
α - P IN E N E bin
THY MOL ma n ool car
va c r o l ene h ydra
BASIL TARRAGON PARSLEY DI LL MINT

O O
OH
1, 3 ,
e
en
-p- i
est r est m e n t h at r
8
a g o le r a g o le ca r v o n e m en thol
NDER LEAV SAFFRON BAY LEAF TURMERIC C H IV E S

RIA O O
CO
ES
OH
HO OH
OH
OH O O
HO
O
O
HO OH
O HO OH
O O
OH
OH
O
OH O O
O
S S
O OH O O
HO
OH OH
pr
di
de
-d e c i α - c r o cin 1, 8 - C o p y l i s u lf i
2
ceno ic a I N E O LE c u r c u min d
CA R
DA M O M CLOVES CUMIN RIANDER SEED L EM
ONGRASS
O OH
C
OH
O
O
O
UM O
1, 8 - c HYD
C
i n e o le eugenol IN A LD E l i n a lo o l ci t ra l
CARAWAY CINNA MON VANILLA STAR ANISE NUTMEG

OH
O
O O
O
O
nn
a m al d e h y d
ci
CARVONE v a n i ll i n a n e t h o le sa b i n e n e
GINGER paprika OH
PEPPER cayenne M A CE
O
O O
N
OH
O
H
N
HO O
OH
TE
O
z in
g ib e r e n e
cap
s a n t hin P I P ER I N E cap s aicin R P IN E N -4- O L

T HE C HE MI S T R Y O F A G R A P E F R UI T
INTERACTIONS WITH DRUGS
O O
O
BERGAMOTTIN
Grapefruit, and grapefruit juice, is known to WHAT CAUSES A GR APEFRUIT’S COLOUR?

interact with a large number of drugs, usually
resulting in adverse effects. These interactions
are caused by a class of compounds called
furanocoumarins, in particular the compounds
bergamottin and dihydroxybergamottin.
LYCOPENE
These compounds inhibit some forms of an
enzyme responsible for breaking down drugs in The colour of pink and red grapefruits is caused by the compound lycopene.
the body. As the prescribed dose of drugs takes This is a compound composed entirely of carbon and hydrogen atoms. The
into account how quickly the drug is broken down compound absorbs all but the longest wavelengths of visible light, causing it to
in the body, this can lead to higher concentrations appear red.
of the drug in the bloodstream, which in turn can
result in unpleasant side effects. Lycopene is also the compound responsible for the colouration of tomatoes. It
is also used as a food colouring due to its strong colour and lack of toxicity.

Image by Aleph, http://commons.wikimedia.org
THE CHEMISTRY OF A LEMON
WHAT MAKES LEMONS SOUR?
O OH
O O
HO OH
OH
CITRIC ACID
The sour taste of lemons is caused by the presence

of organic acids. The major acid in lemons is citric
acid, which makes up around 5 to 6% of the lemon’s
juice.
V ITA MIN C , LEMON S & SCURV Y
Other acids are also present, although in much
lower concentrations than citric acid. Malic acid Lemons contain high levels of vitamin
is one of these, present at around 5% of the HO C, also known as ascorbic acid. The
concentration of citric acid. OH levels in lemons are around 50mg per
100g, on a par with oranges and around
O double the amount of limes.
O Vitamin C deficiency can lead to scurvy,
HO O OH a disease that causes loss of teeth,
OH jaundice, and eventually death. In the
1700s, all British ships were required to
OH provide a lemon juice ration to seamen
O OH to guard against this disease.
VITAMIN C (ASCORBIC ACID)
MALIC ACID

Photo: A Brunning. Graphic shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. BY NC ND
The Chemistry of AN ONION
AMINO ACID SULFOXIDES
S
O
1-PROPENESULFENIC ACID
S
O N I O N O D O U R & T H I O S U L F I N AT E S
SYN-PROPANETHIAL-S-OXIDE
O O ALLICIN
As onions are sliced, they release a class of
enzymes, allinases, which break down amino
acid sulfoxides. A specific compound produced S R' S
during this process is 1-propenesulfenic acid,
which is rearranged by another enzyme, called R S S
lachrymatory factor synthase, to produce syn-
propanethial-S-oxide. Production of this gas Thiosulfinates are the primary flavour and odour producing molecules
peaks 30 seconds after mechanical damage to in an onion. These compounds are not present in intact bulbs, but are
the onion, and it stimulates sensory neurons in formed via enzymatic reaction from sulfur amino acids. Allicin is one of
the eye causing a stinging sensation; the eye these compounds, which in turn quickly breaks down to form other sulfur-
therefore produces tears to flush it out. containing compounds.

T HE CHEMIS T RY OF ASPA R AGUS
ASPARAGUSIC ACID
O
S
S
OH
ASPARAGUSIC ACID
Asparagusic acid is a type of organosulfur

compound which also contains a carboxylic acid
group. It is seemingly unique to asparagus and
not found in other related vegetables. WHY DOES ASPARAGUS MAKE URINE SMELL?
It has been hypothesised that the breakdown of S All four of the compounds on the left
asparagusic acid into a variety of compounds, H3C SH have been identified as being probable
shown to the right, could be responsible for the H3C CH3
contributors to the smell of urine after
odour detected in the urine of some people after METHANETHIOL DIMETHYL SULFIDE eating asparagus.
eating asparagus.
O O It has been suggested by several
Strangely, research has suggested that some studies that methanethiol & dimethyl
people who secrete the compounds in their sulfide are the primary odour-causing
H3 C S CH3
urine can’t smell them, whilst some people don’t S compounds, whilst dimethyl sulfoxide
secrete the compounds but can smell them in & dimethyl sulfone modify the smell to
the urine of others. It is currently unknown as to H3C CH3 O
give a ‘sweet’ aroma.
whether this complicated combination of traits DIMETHYL SULFOXIDE DIMETHYL SULFONE
has a simple genetic basis.

T H E C H E M I S T R Y O F A N AV O C A D O
WHAT MAKES AVOCADO GO BROWN?
OH O
OH O
ENZYME
(polyphenol oxidase)
OXYGEN
CATECHOL 1,2-BENZOQUINONE
(type of polyphenol)
Avocados contain a class of compounds called

phenols. These compounds can be converted
to compounds called quinones when exposed to
oxygen in the air - this process is hastened by the PREVENTING THE BROWNING OF AVOCADOS
enzyme polyphenol oxidase.
Some of these quinone compounds are toxic to

bacteria, and so the process is beneficial for the
fruit. However, the quinones can also react with
themselves to form long polymer chains, causing
the brown colouration. This also occurs in many 3 HOURS 6 HOURS 9 HOURS 12 HOURS
0 HOURS
other fruits. Avocados brown quickly as they have
a large amount of polyphenol oxidase.
Contrary to popular belief, leaving the stone in the avocado or guacamole
The polymeric compounds causing the brown doesn’t slow browning, as it doesn’t block oxygen. Covering with clingfilm
colouration are melanin pigments. Melanin is also can block oxygen, and hence delay browning. Adding lemon or lime juice, or
the primary pigment determining skin colour in chilling the avocado, can also delay browning, as it inhibits the activity of the
humans. polyphenol oxidase enzyme.

This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives Licence. Photo: © Andy Brunning 2014. BY NC ND
T HE C HE MI S T R Y O F B E E T R O O T
WHY IS BEETROOT RED?
OH
O
RO OH
RO N NH
OH
O-
O O
BETACYANINS
A class of compounds called betacyanins are
responsible for the red colouration of beetroot. The
major compound responsible for the colour is betanin;
this can be extracted from beetroots and used as a WHY CAN BEETROOT MAKE URINE RED?
red food dye called ‘beetroot red’, which has the E
HO
number E162. O
The same chemical compounds that are responsible
HN
The compounds vulgaxanthin & indicaxanthin are HO for the red colour of beetroot are also responsible for
also found in beetroot, and also contribute towards -
its ability to turn urine red.
O O
its colouration. O
N Betanin is the compound that causes ‘beeturia’.It has
O HO O been suggested that the pigment is usually degraded
O
OH
HO
OH by stomach acid, explaining why the effect is not
N N HO OH always evident - only when the stomach acid’s pH is
NH NH O OH
O not low enough to degrade the pigments are large
O- OH O enough amounts present in urine. However, it has also
O OH OH
O
O been suggested that genetic factors could influence
OH whether people experience beeturia.
INDICAXANTHIN VULGAXANTHIN
BETANIN

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THE CHEMISTRY OF CLOVES
WHY DO CLOVES HELP TOOTHACHE?
OH
O
EUGENOL
The essential oil of cloves is often touted as a

remedy for dental pain; it is composed mainly of
70-85% eugenol, 15% eugenyl acetate, and 5-10%
ß-caryophyllene.
Eugenol has antiseptic and anti-inflammatory

WHAT GIVES CLOVES THEIR AROMA?
properties. As well as this, it has anaesthetic O
properties, due to its ability to inhibit movement O
of sodium ions in peripheral nerves. Additionally, it
can act as an antifungal and antibacterial agent. O
However, the FDA believes there is currently not
enough evidence of its effectiveness for it to be
recommended in treating tooth pain - though some OH
research has shown it may be of use in creams for
2-HEPTANONE METHYL SALICYLATE
the treatment of premature ejaculation.
The aroma of cloves is partly influenced by eugenol, but minor compounds
Eugenol can also have toxic side effects in larger such as 2-heptanone and methyl salicylate are also significant contributors.
quantities - as little as 5-10 ml of undiluted essential Interestingly, 2-heptanone is also a compound secreted by honeybees; they
oil could cause these. It can damage the liver and
secrete it when biting intruders in their hives, and the anaesthetic effect
respiratory system.
paralyses the intruding creature and allows it to be removed.

PICTURE: Tijmen http://www.freeimages.com, ID:359963
THE CHEMISTRY OF COFFEE
WHY IS COFFEE BITTER?
5-CAFFEOYLQUINIC ACID
OH
HO
O
HO OH
O
OH
O
HO
Chlorogenic acids account for up to 8% of the

composition of unroasted coffee beans. More than
40 different varieties have been identified in green
coffee beans, with 5-caffeoylquinic acid the most
prevalent. T H E C A F F E I N E CO N T E N T O F CO F F E E
Chlorogenic acid content decreases when The caffeine content of coffee is
coffee beans are roasted, as they react to form O CH3 variable but is approximately 100mg
quinolactones, phenylindanes & melanoidins. in a cup.
These contribute to flavour and bitterness. H3C N
3-CAFFEOYLQUINIC-1,5-LACTONE O
N Caffeine works by blocking the action
of a group of brain chemicals called
O adenosines, which work to naturally
O N trigger tiredness.
HO OH O N
O The amount of caffeine in your
OH
CH3 bloodstream peaks 15 to 45 minutes
HO after ingestion.

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THE CHEMIS TRY OF CORIANDER
CHEMICAL COMPOSITION
O
OH
2-DECENOIC ACID
A range of aldehyde compounds are largely

responsible for the aroma of coriander leaves.
The largest proportion of these are those
aldehydes with 6-10 carbon atoms, particularly
decyl (10) and nonyl (9) aldehydes.
Other ma jor constituents of the leaves are

2-decenoic acid, decanoic acid (also known as WHY CAN CORIANDER TASTE ‘SOAPY’?
capric acid) and tetradecenoic acid.
Coriander leaves contain high levels of
organic compounds called aldehydes.
The chemical composition of coriander seeds is O
The same aldehydes, or similar, are often
slightly different, with the alcohol linalool being DECANAL commonly found in soaps and lotions.
the ma jor constituent.
O However, perception of this facet of

HO coriander’s taste isn’t purely chemical.
2-DECENAL
Scientists have discovered that dislike of the
O
taste of coriander may also be influenced, to
an extent, by genetic factors. Studies have
also suggested that crushing coriander
2-UNDECENAL
LINALOOL leaves may lead to faster breakdown of
aldehydes, diminishing the soapy taste.

THE CHEMISTRY OF GARLIC
WHAT CAUSES GARLIC BREATH?
There are four major volatile organic compounds responsible for

‘garlic breath’: diallyl disulfide, allyl methyl sulfide, allyl mercaptan,
and allyl methyl disulfide. None of these compounds are present in
garlic until it is crushed or chopped.
O
S S
S GARLIC'S ANTIBACTERIAL PROPERTIES
ALLICIN ALLYL METHYL SULFIDE S S S S

S S
When garlic is mechanically damaged, enzymes convert the DIALLYL SULFIDE DIALLYL DISULFIDE DIALLYL TRISULFIDE
compound alliin to allicin (which gives chopped garlic its aroma). This
is broken down further into the afore-mentioned volatile compounds.
Sulfur-containing organic compounds give garlic antibacterial properties.
Allyl methyl sulfide is broken down in the body more slowly than the Antimicrobial effects have been shown to increase as the number of sulfur
other three compounds, so it is the primary volatile responsible for atoms in the compounds increases.
garlic breath. It is excreted via sweating, breathing, and through the The organosulfur compounds can penetrate the cell membranes of bacteria
urine, and its effects can last up to a day! cells, and combine with certain enzymes or proteins to alter their structure,
A few foods have been shown to have some effect on reducing garlic injuring the cells. Allicin, formed initially when garlic is crushed, also has
breath, including parsley & milk. antibacterial properties.

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T HE C HE MI S T R Y O F H O NE Y
HOW DO BEES MAKE HONEY?
OH
HO HO O
O OH
HO O SUCROSE
OH primary sugar in
many nectars
HO OH
When bees harvest nectar, it is stored in their honey
stomachs, separate from their normal stomach. The
nectar is mixed with enzymes which break down
the larger sugars in the nectar, such as sucrose,
into the smaller sugars glucose and fructose.
WHY DOESN’T HONEY GO OFF?
The forager bee then passes it on to a house bee,
who regurgitates and re-drinks the nectar over a OH OH O
20 minute period, breaking down the larger sugars H
further. HO
OH O O
OH
O OH
OH
O
OH
OH OH H
GLUCONIC ACID HYDROGEN PEROXIDE
HO
HO OH
Honey has such a low water content, it draws water from its surrounding
OH HO OH
environment, meaning it can dehydrate bacteria, thus preventing spoilage.
GLUCOSE FRUCTOSE
Gluconic acid is the dominant acid in honey, produced by the action of bee
The nectar is deposited in the honeycomb, and the secretions on glucose. It, and other acids, give honey a low pH of between 3
bees fan it to hasten water evaporation, until the and 4; this, along with the fact it also contains small amounts of hydrogen
water concentration falls to around 17%. peroxide, makes it too hostile for bacterial growth.

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THE CHEMISTRY OF JAM-MAKING
SUGAR FRUIT ACIDS
HO O OH
O O
OH
O HO OH
HO OH
OH CITRIC ACID
O O
HO (occurs naturally in citrus fruits)
SETTING & PECTINS A frequent cause of jam not
HO OH setting is a lack of acidity. Fruits
COOH OH COOCH3 OH themselves provide some acids
OH
naturally, but often extra acid
O O O O O will need to be added - this is
SUCROSE OH OH
OH OH commonly in the form of citric
(table sugar) O O
O O acid, but tartaric acid can also be
used. A pH of between 2.8-3.3 is
The majority of jam-making OH COOCH3 OH COOH needed to help the pectin form
recipes call for an equal weight n
a gel and allow the jam to set
of fruit and sugar. Sugar boosts PECTIN properly.
the gel-forming capability of (typical chemical structure)
the jam by drawing water away
from pectins. It binds the water, Pectin is made up of a large number of sugar molecules bonded together OH O
meaning that with high levels in a long chain. The pectin content varies from fruit to fruit; fruits lower in
of sugar, there is no longer pectin require more pectin to be added, either in the form of commercial HO
enough water available in the pectin or by addition of fruit whose pectin content is higher. The ‘setting OH
jam to support microbial growth, point’ when boiling jam is ~104˚C; the pectin chain binds to itself, forming a
gel network that traps liquid as the jam cools and helps it set. O OH
therefore imparting a natural
preservative effect. TARTARIC ACID
(found in grapes)
65-69%
Required FINAL SUGAR LOW IN PECTIN
Pears, peaches, cherries, strawberries, raspberries,
HIGH IN PECTIN
Apples, gooseberries, blackcurrants,
2.8-3.3
CONTENT OF JAM blackberries, sweet plums, blueberries, elderberries. sour plums, grapes, citrus rind. OPTIMAL pH FOR SETTING

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THE CHEMISTRY OF NUTMEG
WHY IS NUTMEG HALLUCINOGENIC?
MYRISTICIN
Nutmeg contains compounds that lend it a

hallucinogenic effect in larger quantities than
those usually used in cooking. Around a tablespoon
is enough to produce mild effects.
WHAT ARE THE ADVERSE EFFECTS?
One of the main compounds responsible for this
effect is myristicin, which accounts for up to 1.3% of
raw nutmeg. The exact manner in which myristicin In large doses, nutmeg can cause nausea, vomiting,
induces these effects is unclear, however, and the
O O flushing, an elevated heart rate, euphoria and
same effects are not observed with ingestion of hallucinations. A dose of 10-15g is required before
pure myristicin, suggesting other compounds, such acute intoxication occurs, and the side effects can
O
as elemicin & safrole, must also contribute. last for several days after ingestion.
O It has been suggested that nutmeg’s hallucinogenic

O O
NH2
properties could be the result of myristicin being
broken down into MMDA, a compound similar to
Ecstasy, in the liver. However, this has only been
O
O observed in rats, and there has been no proof of
MMDA this breakdown occuring in humans.
ELEMICIN SAFROLE

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T HE C HE MIS T R Y OF R A S P B E R R IE S
THE AROMA OF RASPBERRIES
O
HO
RASPBERRY KETONE
4-(4-hydroxyphenyl)butan-2-one
The chemical compound commonly referred to

as ‘raspberry ketone’ is the primary compound
responsible for the aroma of raspberries. Around 1
to 4 milligrams of the compound can be extracted IS THE GALAXY RASPBERRY-FLAVOURED?
from a kilogram of raspberries.
Ethyl formate is one of a number of chemicals that contribute towards
Raspberry ketone, also found in cranberries and the flavour of raspberries. In 2009, astronomers detected ethyl formate
blackberries, is commonly used as an aroma molecules at the centre of our galaxy, prompting a spate of news articles
compound in perfumes, as well as in cosmetics proclaiming that the galaxy tastes of raspberries. Other simple molecules,
and in small amounts as a food additive. Because such as methanol, have also been detected, however, so the notion that the
it occurs in quite low amounts, natural raspberry galaxy tastes of raspberries is something of a romanticised one!
ketone is an expensive additive, though synthetic
versions of the compound are cheaper.
O
Studies in rodents have suggested that raspberry ETHYL FORMATE
ketone may have an anti-obesity effect, but there Tastes of raspberries, smells like rum
is currently no reliable scientific evidence for this
effect being observed in humans. H O

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THE CHEMISTRY OF TEA
POLYPHENOLS IN TEA
OH
OR2
OH
O
HO O
OH
THEAFLAVINS
HO O
OH
OR1
OH THE EFFECT OF MILK ON POLYPHENOLS

A strong cup of tea usually contains around 180-
240mg of polyphenol compounds, Compounds OH The compounds in tea derived from
called catechins are the building blocks of black catechins can have antioxidant effects
OH
tea polyphenols; they are oxidised to form on the body - research has shown
theaflavins and thearubigens. these could have beneficial effects on
HO O cardiovascular health.
R
Theaflavins comprise 3-5% of black tea, and are
responsible for its red-orange appearance. It’s suggested that the casein proteins
in milk could bind to polyphenols and
OR1
‘Thearubigens’ is the term for a wide range of as a result prevent their antioxidant
polyphenols whose structures remain largely OH effects, but research on this subject
CATECHINS remains conflicted.
unknown, but they are also thought to contribute
to tea’s colour & taste.

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A GUIDE TO THE DIFFERENT TYPES OF FAT
Fat is an essential part of our diets, and has a number of important roles in the body. However, there are different types, and there are health
concerns surrounding eating too much of some types of fat. Here, we look at what distinguishes different types of fat, and their effects on the body.
TRIGLYCERIDES & FATTY ACIDS SATURATED FATS MONOUNSATURATED FATS
O O
OH OH
OLIVE
Contain no carbon-carbon double bonds. Saturated fats Contain one carbon-carbon double bond. They are liquids
are solids at room temperature. They increase levels at room temperature, but solidify when chilled. They reduce
of LDL in the bloodstream. They have previously been levels of LDL in the bloodstream, thereby decreasing the
associated with heart disease, though more recent studies total cholesterol to HDL ratio (HDL helps take cholesterol
and reviews have called this association into question. back to the liver where it can be disposed of).
O
POLYUNSATURATED FATS TRANS FATS
O
H2C O O
O
HC O OH
OH
O
H2C
O
CANOLA
Triglycerides account for around 95% of the fat in our diet, and
are formed from the combination of glycerol and three fatty
acid molecules. The three fatty acids are often different, and Contain two or more carbon-carbon double bonds. They Contain carbon-carbon double bonds in a trans rather than
the chemical structures of these fatty acids defines the type are liquids at room temperature, but they start to solidify cis configuration. Formed artificially, via a process called
of fat. Cholesterol is made in the liver, and transported around when chilled. They are split into omega-3 and omega-6 hydrogenation; also found naturally in small amounts in
the body by low density lipoproteins (LDL) and high density fatty acids. Polyunsaturated fats help reduce LDL levels, meat and dairy products. They raise LDL, and are associated
lipoproteins (HDL). Different fats affect LDL and HDL differently. decreasing the total cholesterol to HDL ratio. with heart disease. Many countries are phasing them out.

Aroma Chemistry
THE AROMA OF FRESH-BAKED BREAD
WHAT CREATES BREAD’S AROMA?
INGREDIENTS FERMENTATION BAKING
The compounds that help to generate baked bread’s aroma

are influenced by the ingredients of the bread, and also by
compounds generated during the fermentation process.
Caramelisation and non-enzymatic Maillard reactions during
baking help produce characteristic aroma compounds.
A SELECTION OF SIGNIFICANT AROMA COMPOUNDS FROM BAKED BREAD
O O O O
OH O
O OH N N
MALTOL ISOMALTOL 2-ACETYL-1-PYRROLINE 2-ACETYLTETRAHYDROPYRIDINE
Both formed from D-fructose. Well- Key odorant in wheat- Also a significant crust odorant. It
known contributors to bread and bread bread crust, responsible for and 2-acetyl-1-pyrroline are both
crust flavour and aroma. cracker-like properties. have low odour thresholds.
O O S
O
(E)-2-NONENAL
3-METHYLBUTANAL METHIONAL
3-methylbutanal (malty), found in the crust, has a significantly

O higher value in the crust of rye breads, as does methional (also a
key odorant in the crumb). Diacetyl adds buttery notes.
(E,Z)-2,6-NONADIENAL
No one compound conjures up the smell of
Amongst the key odorants of bread crumb; baked bread; instead a mixture of compounds
also found in the crust. Weirdly enough,
IN SHORT are responsible. 2-acetyl-1-pyrroline is a
these are also key odorants of cucumber. significant contributor to the crust aroma.

THE CHEMICAL STRUCTURES OF VITAMINS
Vitamins are the essential nutrients that our body needs in small amounts. More specifically, an organic compound is defined as a vitamin when
it is required by an organism, but not synthesised by that organism in the required amounts (or at all). There are thirteen recognised vitamins.
VITAMIN A VITAMIN B1 VITAMIN B2 VITAMIN B3 VITAMIN B5

OH
O O O O
N N+ HO
OH OH
OH HO
N S OH NH2 N OH
NH2
OH H
RETINOL THIAMIN OH
active form in mammalian tissues N N O
can also occur in pyrophosphate ester form N N
NH PANTOTHENIC ACID
Important for eyesight. Also strengthens Used to keep nerves & muscle tissue NICOTINIC ACID NICOTINEAMIDE also occurs in pyrophosphate ester form
N
immune system and keeps skin and linings healthy. Also important for processing of niacin is collective name for these compounds
of parts of the body healthy. carbohydrates and some proteins. O Important for manufacturing red blood cells
Helps with digestion and digestive system health. and maintaining a healthy digestive system.
RIBOFLAVIN
excess turns urine bright yellow Also helps with the processing of carbohydrates. Also helps process carbohydrates.
VITAMIN B6 VITAMIN B7 Important for body growth, red blood cell

production, and keeping the eyes healthy.
Also helps processing of carbohydrates.
VITAMIN C VITAMIN D
O
O O
NH H O
HO
HO P OH
O OH HN OH VITAMIN B12
OH HO
H S O
N H2NOC O OH
PYRIDOXAL PHOSPHATE BIOTIN OH
active form in mammalian tissues produced by intestinal bacteria CONH2
ASCORBIC ACID CHOLECALCIFEROL
H2NOC deficiency can cause scurvy natural form; different form used in supplements
Helps make some brain chemicals; needed Needed for metabolism of various CONH2
N R N
for normal brain function. Also helps make compounds. Often recommended for
Co + Important for a healthy immune system; Important for bone health and maintaining
red blood cells and immune system cells. strengthening hair, but evidence is variable.
H helps produce collagen, used to make skin the immune system function. May also have
N N
and other tissues. Also helps wound healing. a preventative role in cancers.
H2NOC
VITAMIN E VITAMIN B9 CONH2
O
NH
N VITAMIN K Key
O OH N
O HO O
Vitamins can be divided broadly into two classes.
HO
OH O
O N O
H
O N O O P O WATER-SOLUBLE VITAMINS
HN N
H These vitamins are not stored in the body.
O-
H2N N N HO As such, generally, they are required more
O frequently than the fat-soluble vitamins.
ALPHA-TOCOPHEROL FOLIC ACID COBALAMIN MENADIONE
group includes tocopherols & tocotrienols found as tetrahydrofolate in food usually contains CN as the R group
all K vitamins are menadione or derivatives FAT-SOLUBLE VITAMINS
These vitamins are stored in the liver and
An antioxidant that helps prevent damage Important for brain function & mental Important for the nervous system, for Helps blood clot properly, & plays a key role fatty tissues until required. As such, they can
to cells and may have a preventative role in health. Aids production of DNA & RNA. making red blood cells, and helps in the in bone health. Newborns receive vitamin K be harmful if too much is taken in.
cancer. Also helps make red blood cells. Important when tissues are growing quickly. production of DNA and RNA. injections to prevent bleeding.

THE CHEMISTRY OF BRUSSELS SPROUTS
THE BITTER TASTE OF SPROUTS
OH
O -
HO O OH
S N S
HO O
OH O
R
GLUCOSINOLATES
Family of compounds in cruciferous vegetables
Glucosinolates are a class of compounds found
naturally in a range of green vegetables, including
brussel sprouts. They are broken down into
compounds called isothiocyanates when the plant is
damaged or cooked.
These isothiocyanates have similarities with the POTENTIAL BENEFITS OF SULFORAPHANE

synthetic compounds PTC & PROP. PTC only tastes
bitter to around 70% of people. To the other 30%, N O
S
it is completely tasteless. Although it is not the only
factor in dislike of brussels sprouts, ability to taste
C R C S
PTC & PROP and sensitivity to bitter vegetables S N
appear to be strongly correlated, and has a heritable ISOTHIOCYANATES SULFORAPHANE
genetic basis. Breakdown products of glucosinolates Formed from glucosinolates
SH
S
One of the isothiocyanates that glucosinolates can be broken down into is
HN N
sulforaphane. This compound is partly responsible for the bitterness of overcooked
N NH2 brussels sprouts, but it is also being studied for its antioxidant properties.
H O
Additionally, it has been suggested that it could have a protective effect against
PHENYLTHIOCARBAMIDE PROPYLTHIOURACIL neurodegenerative disorders, but more research is required to investigate this.
(PTC) (PROP)

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T HE CHEMIS T RY OF GINGER
FLAVOUR, AROMA & PUNGENCY
ZINGIBERENE
30% of essential oil
Ginger’s flavour is influenced by a number of

compounds. The pungency of fresh ginger comes
from gingerol, whilst flavour also comes from
zingiberene.
Cooking ginger breaks down gingerols into the POTENTIAL HEALTH BENEFITS OF GINGER
compound zingerone, which is less pungent, and a
O O OH
significant contributor to ginger’s flavour. Another
class of compounds formed during cooking are O O
the shogaols, which also contribute to flavour &
pungency. HO HO
O SHOGAOL GINGEROL
Produced when ginger is dried/cooked Active constituent of fresh ginger
O
A number of the compounds in ginger are bioactive. Shogaol has a strong anti-
coughing effect, whilst gingerol has anti-inflammatory & analgesic properties.
Studies have also suggested that [6]-gingerol inhibits production of new blood
HO vessels, which may make it useful in the treatment of tumours. Ginger has
ZINGERONE
additionally been found to be more effective than a placebo for treating nausea
Formed when ginger is cooked during pregnancy and chemotherapy.

A GUIDE TO COMMON FRUIT ACIDS
Most people probably know that lemons and other citrus fruits contain citric acid – but it’s just one of a number of different organic
acids that can be found in fruits. Here we look at a number of the most common acids, and the various fruits that they are found in.
H H
O O O O O
H
O C O
H O C H C H O C H C
C H C O H
C C O
C H C H C H H
H O C C O H
H
O H O O O O
H
H H
CITRIC ACID MALIC ACID TARTARIC ACID
The main acid in citrus fruits is, unsurprisingly, citric acid. Malic acid is the main acid in most stone fruits such as cherries, Tartaric acid is the principal acid in fewer fruits than citric and
Lemons and limes have particularly high levels of this apricots, peaches, and nectarines. It’s also found in high amounts malic acid. However, it is the main acid in grapes, which also
compound. It is also the main acid in a number of berry fruits, in apples, and in lower amounts in bananas. Though watermelons contain malic acid. Red grapes have higher levels of tartaric
including strawberries, raspberries and gooseberries. have a low acid content, their principal acid is also malic acid. acid. The main acid of avocado and tamarind is also tartaric acid.
O
O O O O OH
OTHER ORGANIC ACIDS O O HO
HO
OH
HO HO
OH OH OH HO OH
HO
Citric, malic, and tartaric acids are not the only organic acids OH
O O OH
present in fruit – a number of other acids are also present,
albeit in significantly smaller quantities. To the right, a small
selection of these compounds are shown, along with a brief SUCCINIC ACID OXALIC ACID BENZOIC ACID ISOCITRIC ACID QUINIC ACID
note of some of the fruits in which they’re often found. Apples and some berries Small amounts in berries Present in cranberries Present in blackberries Plums & kiwifruit

THE CHEMISTRY OF ICE CREAM
Ice cream is a combination of air, ice crystals, fat globules, and a liquid syrup. These are combined to make a colloid, a solution with very small
insoluble particles suspended in it. This graphic looks in detail at the components of this colloid, and some molecules that produce ice cream flavours.
FATS, PROTEINS, & EMULSIFIERS FLAVOURS AND COLOURS

O
C
H2C O R
O 1 LIQUID FAT R5
H
R6 HO N
HC O
C
R2 EMULSIFIER MOLECULES R1 O+
R7
O O
C
MILK PROTEINS R2 R4 H3CO
R3 CH3
H2C O R3
FAT CRYSTALS
FAT ( TRIGLYCERIDE) ANTHOCYANINS VANILLIN SKATOLE
R = fatty acids
Fats are important for the creaminess of ice cream. Proteins from Natural ice cream flavours contain a number of flavour-contributing
milk form a membrane around the fat droplets, making it harder compounds. Flavouring can also be achieved artificially. Artificial
for them to come in contact with each other. Emulsifiers replace vanilla flavouring is often simply vanillin; other artificial flavours are
some milk protein on the surface of the fat droplet. As ice cream is more complex. Other compounds can be used as flavour enhancers
made, some of the fat in the droplet solidifies, and the fat ‘needles’ – an unusual example is skatole, also found in faeces, but which has a
that form help droplets to partially cluster. These clusters, along floral odour at lower concentrations. Colours can be added artificially;
with milk proteins, help stabilise air bubbles in the ice cream. anthocyanins from plants are amongst the colouring agents used.
THE STRUCTURE OF ICE CREAM STABILISERS

ICE CRYSTALS 30% ALGINIC ACID
OH
AIR BUBBLES 50% OH OH Sodium alginate is the
O O
sodium salt of alginic
FAT DROPLETS 5% O O acid. Another stabiliser
HO OHO O that can be obtained
LIQUID SYRUP 15% from seaweed is
O OH n
carrageenan.
% by volume for typical composition m
During freezing, most water is frozen into ice. Small ice crystals are Stabilisers are added in small amounts (~0.2%) to ice cream. Often
needed for smooth ice cream. Beating and aeration occur at the extracted from plants, a common example is sodium alginate,
same time as freezing to form small air bubbles, stabilised by de- the sodium salt of alginic acid, extracted from brown seaweeds.
emulsified fat. Air makes up 30-50% of ice cream’s final volume. Stabilisers reduce the rate at which ice cream melts, add
Sugar sweetens the ice cream, and lowers the freezing point of smoothness, and increase the viscosity of the liquid phase of ice
water, reducing the amount of ice. Soft ice cream contains less ice. cream. Use of multiple stabilisers can produce synergistic effects.

THE CHEMISTRY OF CAMEMBERT
Camembert is a surface-ripened cheese made from cow’s milk. What’s behind its strong smell and gooey texture? This graphic takes a look.
WHY DOES CAMEMBERT SOFTEN AS IT RIPENS?
LACTIC
O
ACID pH 4.6 pH 7.0
Formed by the OH As the lactic acid is broken down by the surface
breakdown of lactose
in the cheese mould, the acidity of the cheese decreases.
OH
Lactic acid is formed by the breakdown of lactose in the cheese.

The surface mould that forms on the camembert, called penicillium
camemberti, can then break down this lactic acid into carbon dioxide and WHAT MAKES CAMEMBERT SMELL SO STRONG?
water. This raises the pH of the cheese, from around 4.6 to 7.0.
O
pH 5.0 pH 7.0 O
O N
O S H H
2+ OH
–
P –
Ca O
H
O –
O
O
2 3
ISOVALERIC ACID DIACETYL METHIONAL AMMONIA
CALCIUM PHOSPHATE LOW Ca 3(PO 4) 2 HIGH Ca 3(PO 4) 2
A range of compounds contribute to camembert's aroma. These include

Calcium phosphate helps hold casein protein micelles together in the isovaleric acid, which smells of feet, diacetyl, which has a buttery aroma, and
cheese. As lactic acid is broken down and pH increases, calcium phosphate methional, which smells like boiled potatoes. Other compounds are 1-octen-3-
becomes less soluble, and precipitates on the cheese’s surface. This draws one (mushroom), methanethiol (cabbage) and butyric acid (sweaty). The smell
the calcium phosphate from the cheese's centre, making it soften. of ammonia increases as the cheese ripens and amino acids are deaminated.

THE CHEMISTRY OF BLACKCURRANTS
COLOUR & ACIDS
OH
OH OH
HO O+ HO O+
OH OH
R R
OH OH
CYANIDIN (L) & DELPHINIDIN (R) GLYCOSIDES

R group = sugar
The purple colour of blackcurrants is down to the

presence of anthocyanin glycosides. Of these, the
major glycosides present are those of cyanidin
and delphinidin. The sugar group present in these
glycosides can vary.
Blackcurrants have a very tart flavour, due to a BLACKCURRANTS & CAT URINE
relatively high acid content. Citric acid is the most
prevalent fruit acid in blackcurrants. From a nutrition SH
perspective, they also have a notably high vitamin C O
(ascorbic acid) content, which is more per 100g of
SH HS
fruit than oranges (~150-200mg vs. ~50mg).
O
O
HO
O OH OH p-MENTHA-8-THIOL-3-ONE 4-METHOXY-2-METHYL-2-BUTANETHIOL 4-MERCAPTO-4-METHYLPENTAN-2-ONE
O O
To some, the smell of blackcurrants and blackcurrant bushes is apparently
O strongly reminiscent of cat urine. This is due to the presence of a number of
HO OH O OH thiol-containing compounds. One of the key aroma components, is 4-methoxy-2-
OH
OH methyl-2-butanethiol. Another, 4-thio-4-methylpentan-2-one, is more commonly
known as ‘cat ketone’, because it’s also present in cat urine. At low concentrations,
CITRIC ACID (L) & ASCORBIC ACID (R) it smells of blackcurrant, whereas higher concentrations are less pleasant!

Graphic shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 licence. Photo: CC-BY license, http://www.torange.us/ BY NC ND
THE CHEMISTRY OF BREAD-MAKING
Baking bread may seem like a very simple process. It’s a combination of only four different ingredients: flour, water, yeast, and salt.
However, there’s a lot of science in how these four ingredients interact, and how varying them varies the bread’s characteristics.
1 MIX INGREDIENTS 2 KNEAD THE DOUGH 3 LEAVE TO FERMENT 4 BAKE THE BREAD
FLOUR, WATER & SALT STARCH & SUGAR YEAST & FERMENTATION OTHER INGREDIENTS
OH
FATS
PROTEINS STARCH O OH O
Specifically Composed of many Weaken the gluten
HO OH
glutenin and gliadin sugar molecules network, giving a softer
stuck together OH YEAST R OH bread. Also stabilise
gas bubbles, increasing
loaf volume.
GLUCOSE R = long hydrocarbon tail
WATER ENZYMES
O C O OH NaHCO3 BAKING SODA

GLUTEN GLUCOSE Sodium bicarbonate. Combined with moisture
and acidity, produces carbon dioxide, which
Viscoelastic network Used by yeast for CARBON DIOXIDE ETHANOL
can help bread rise. Can cause bitterness.
that traps gas fermentation. Helps bread rise Boils off during baking
NaHCO3 BAKING POWDER

+ CREAM OF TARTAR
Flour contains high levels of glutenin Flour contains starch, long chains of Yeast are single-celled fungi that help
and gliadin proteins. These classes of connected sugar molecules. Amylase convert sugars in the bread mix into Also sodium bicarbonate, but with cream
proteins are collectively referred to as converts starch to maltose; maltase in carbon dioxide. The bubbles of carbon of tartar (potassium bitartrate), an acid
ingredient that activates the bicarbonate.
gluten. When water is added, these yeast converts this to glucose. Along dioxide formed cause the bread to
proteins form a network held together with other sugars, this can be used rise; kneading makes their size more
by hydrogen bonds & disulfide by the yeast for fermentation, and is uniform. Sour dough breads contain HO
OH
cross-links. Kneading uncoils gluten also involved in the flavour-forming both bacteria and wild yeasts. The
proteins, strengthening the network browning reactions that help to form lactic acid produced by bacteria can O ASCORBIC ACID
O OH
and the dough. the bread’s crust. sometimes give a sour taste.
OH
OH OH More commonly known as vitamin C, it helps

THE ROLE OF SALT O
SOUR DOUGH O to strengthen the dough’s gluten network.
O OH HO O OH
ADDS FLAVOUR TO BREAD HO OH HO OH O OH 100:1 OH A POLYSACCHARIDE

THAT IS PRODUCED BY
SLOWS DOUGH FERMENTATION BACTERIA:YEAST THE BACTERIUM XANTHAN GUM
OH
HO OH
Both feed on sugars;
OH XANTHOMONAS
CAMPESTRIS
STRENGTHENS GLUTEN STRUCTURE yeasts in sour dough
can’t break down
MAKES DOUGH MORE ELASTIC GLUCOSE MALTOSE maltose, bacteria can. LACTIC ACID Used in the production of gluten-free breads.

THE CHEMISTRY OF CANDY
CRYSTALLINE CANDY NON-CRYSTALLINE CANDY
HO
OH
O
HO
OH
O O
HO
HO OH
OH
SUCROSE
FUDGE ROCK CANDY FONDANT LOLLIPOPS CANDY CANES CARAMEL
INTERFERING AGENTS
LOWER SUGAR CONCENTRATION THAN NON-CRYSTALLINE HIGHER SUGAR CONCENTRATION THAN CRYSTALLINE
OH
˚C SUCROSE SOLUTION BOILED AT LOWER TEMPERATURE O OH

˚C SUCROSE SOLUTION BOILED AT HIGHER TEMPERATURE
HO OH
CONTAIN MANY SMALL, FINE CRYSTALS OF SUCROSE OH FROM VERY SATURATED SOLUTION - NO CRYSTALS
GLUCOSE
Generally smooth and creamy. Crystalline candies OH OH Generally hard & brittle. Non-crystalline, or amorphous
contain crystals of sucrose in their finished form; the O candies, form when crystallization is prevented.
sucrose molecules are able to align and form large HO This can be accomplished by the addition of sugars
lattices. They are best formed by slow cooling and little such as glucose and fructose that interfere with the
mixing of a solution for crunchy candies, and faster HO OH development of crystals. Often, their mixtures are too
cooling and lots of mixing for smooth candies. FRUCTOSE viscous for crystals to form.

THE CHEMISTRY OF EGGS & EGG SHELLS
Eggs are one of the most versatile kitchen ingredients; there are numerous ways of cooking them on their own, and they can also
be used to help create a range of other foods. Here, we take a look at what they’re made of, and how they change during cooking.
EGG COLOUR & COMPOSITION COOKING EGGS

OH
HEAT
HO
LUTEIN
BEFORE COOKING AFTER COOKING
OH
Egg proteins begin in the raw egg as folded chains,

but as they are heated they begin to denature and
HO unfold. Interactions between the unfolded proteins
create a three-dimensional network, trapping the
ZEAXANTHIN water and causing the egg to solidify.
The yellow colour of egg yolks is due to the presence EGG SHELL COMPOSITION S FeS
of the carotenoid pigments lutein and zeaxanthin. H H
Artificial additives aren’t permitted, but additives O
such as beta-carotene and marigold petals can be HYDROGEN SULFIDE IRON (II) SULFIDE
2+ CALCIUM CARBONATE
added to chicken feed to influence the yolk’s colour. Ca -
C
O O-
Hydrogen sulfide, formed by the reaction of sulfur-
EGG WHITE PROTEINS containing proteins in the albumen, is the compound
Calcium carbonate is the main component of
eggshells. Nanoparticles of calcium carbonate are that gives cooked eggs their characteristic smell.
OVALBUMIN CONALBUMIN OVOMUCIN OTHERS When eggs are cooked for a long time it can react
arranged into ordered crystals by proteins, forming a
with iron in the yolk, forming iron sulfide, and giving
calcite shell. The colour of the eggshell comes from
a green hue to the yolk surface.
porphyrin pigments on the shell’s surface.
54% 12% 2% 32%
ALBUMEN pH pH AFTER
7.6 OF FRESHLY 9.2 SEVERAL DAYS
HOOC
N HN PROTOPORPHYRIN IX LAID EGG OF STORAGE
About 90% of the egg white is water; the rest of
its mass is mostly protein. Ovalbumin’s purpose Brown pigment; the presence of the
NH N
is thought to be nutrition for the developing HOOC pigment oocyanin causes eggs to have a Albumen pH increases as CO2 diffuses out through
chick; Ovomucin helps thicken the egg white; and blue or green colouration. the shell. Albumen adheres more strongly to the shell
conalbumin binds iron & guards against infection. at lower pH, making it harder to peel boiled eggs.

THE CHEMISTRY OF ELDERFLOWER & ELDERBERRIES
It's the time of year when elderflower bushes are bursting into bloom in the countryside. Here, we look at the chemistry of the flowers and the berries!
AROMAS OF ELDERFLOWER & ELDERBERRIES
O OH O O
cis-ROSE OXIDE HOTRIENOL NEROL OXIDE NONANAL
OH
OH O OH
LINALOOL α-TERPINEOL HEXANAL (Z)-3-HEXENOL
The compounds that make significant contributions to the aroma of ELDERBERRY COLOUR & TOXICITY
elderflowers are cis-rose oxide, nerol oxide, hotrienol, and nonanal.
OH
Other compounds that contribute to the floral odour include linalool and
OH OH
α-terpineol, whereas hexanal and (Z)-3-hexenol add grassy odours. Cl–
N
HO O+ O OH
CYANIDIN
3-SAMBUBIOSIDE
O O OH
O O
OH
O
O OH SAMBUNIGRIN OH
HO O
OH OH OH
O OH
OH
β-DAMASCENONE DIHYDROEDULAN 2-PHENYL ETHANOL PHENYLACETALDEHYDE

Coloured anthocynanins cause the colour of elderberries; the most abundant
is cyanidin 3-sambubioside. Their high citric acid content contributes to their
The key compounds that contribute towards the characteristic aroma of acidity. The leaves and stems of the plant, as well as elderberry seeds, contain
elderberries are β-damascenone and dihydroedulan, with 2-phenyl ethanol moderate amounts of the cyanide-producing compound sambunigrin and the
and phenylacetaldehyde also present. Several compounds present in the poisonous alkaloid sambucine. As such it's recommended that elderberries are
aroma of elderflowers also contribute, including linalool, and hotrienol. always cooked before eating, as this breaks down these compounds.

THE CHEMISTRY OF PLUMS & PRUNES
PLUM AROMA & WAX BLOOM
HO
O
BENZALDEHYDE LINALOOL
O
O
γ-DECALACTONE
The aroma of plums is down to a number of volatile WHY DO PRUNES HELP WITH CONSTIPATION?
compounds, which include benzaldehyde, linalool,
ethyl nonoate, methyl cinnamate, & γ-decalactone. PRUNES CHEWING GUM
Several six-carbon alcohols, aldehydes, and esters
OH OH
also contribute. OH
The dusty white coating visible on many plums is HO 15g VS 30g
referred to as a ‘wax bloom’. This bloom consists
of long chain alkanes and alcohols (mainly those OH OH
containing 29 carbon atoms), and adds to the flavour SORBITOL (SORBITOL CONTENT PER 100 GRAMS)
of the plum by trapping compounds such as nonanal.
Prunes are dried plums, and are often cited as a home remedy for constipation.
This is due to their relatively high natural levels of the known laxative compound
sorbitol (approximately 15g per 100g). Sorbitol is also responsible for the laxative
O effect of some chewing gums. Phenolic compounds, such as neochlorogenic
NONANAL acids, and the high fibre content of prunes may also aid the laxative effect.

This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives International 4.0licence. BY NC ND
T HE CHEMIS T RY OF R HUB A R B
COLOUR & LAXATIVE EFFECTS
Diferent species of rhubarb contain a wide variety of

anthraquinone compounds. Anthocyanin pigments
are the main compounds responsible for rhubarb’s
red colouration, but the anthraquinones are also
coloured.
Rhubarb also contains various derivatives of these WHY SHOULDN’T YOU EAT RHUBARB LEAVES?
anthroquinone compounds, including compounds
called sennosides. During digestion, these are turned
into active compounds which can have a laxative
efect. Chief among these is the metabolite called
rheinanthrone. Sennosides are also found in senna
plants, and are on the World Health Organisation’s
list of essential medicines.
Rhubarb leaves are relatively high in oxalic acid and oxalate salt content, which can
cause nausea and vomiting if ingested. In Britain in World War I, food shortages
led to recommendations to eat rhubarb leaves, with a number of documented
poisonings as a result. There is still some debate, however, as to whether other
poisonous compounds in the leaves may contribute. The stalks are safe to eat, as
they contain a lower oxalic acid content, the dominant acid being malic acid.
T HE C HE MI S T R Y O F T O M AT O E S
SHOULD TOMATOES BE STORED IN
THE FRIDGE?
O
(Z)-3-HEXENAL
Significant volatile compound in tomatoes
Chilling damages cell membranes in tomatoes, and

inhibits enzyme activity, which can lead to a drastic
loss of volatile compounds. Some of these, such
as the C6 (six carbon) volatiles, do not contribute
significantly to flavour, but others, such as geranial,
WHAT CAUSES THE COLOUR OF TOMATOES?
have a noted impact on factors such as sweetness.
Taking tomatoes out of the fridge for 24 hours
can lead to some recovery of volatile compounds,
however, though only within a week of fridge
storage. It’s also worth noting that storing ripe LYCOPENE
Absorbs all but the longest wavelengths of visible light
tomatoes in the fridge can obviously be beneficial,
to stop them from going off!
Green tomatoes are so coloured because of the presence of chlorophyll. As
they ripen, the pigment lycopene develops; this compound absorbs light
across most of the visible light spectrum, except the red portion, causing
O the tomato to appear red. It absorbs most visible light as a result of its highly
conjugated structure - that is to say, it has lots of alternating double and
GERANIAL
Contributor to sweetness of tomatoes single bonds.

T HE CHEMIS T RY OF WAT ER MEL ON
COLOUR & AROMA
LYCOPENE
Pigment that causes watermelon’s pink colour, also found in tomatoes
The pink colouration of red watermelon flesh is due

to the presence of lycopene. This compound is also
responsible for the colour of tomatoes, but it is found
in even higher levels in watermelon.
The aroma of watermelon is contributed to by
a variety of chemicals, generated by enzymatic
oxidation of fatty acids when the watermelon is cut.
The primary aroma-impact compounds are thought
to be C6 and C9 aldehydes. EXPLODING WATERMELONS
The aldehyde (Z,Z)-3,6-nonadienal is of particular
significance, and is often itself described as having a O N FORCHLORFENURON
fresh, watermelon-like odour. (Z)-3-hexenal, another A growth-promoting chemical approved in the
aldehyde present, also contributes to the smell of US for use on kiwi fruits, raisins, and grapes. It
fresh-cut grass. N N Cl is normally used in low quantities.
H H
O In 2011, farmers in Eastern China were hit by a spate of exploding watermelons.
This was a result of their treatment with forchlorfenuron, a plant growth regulator.
O Forchlorfenuron acts with plant auxins, naturally present hormones that play
an important role in plant growth, to promote cell division and growth. It was
LEFT: (Z,Z)-3,6-NONADIENAL suggested that overuse of forchlorfenuron during wet weather resulted in the
ABOVE: (Z)-3-HEXENAL exploding watermelons, affecting an area of approximately 115 acres.

Graphic shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 licence. Photo: Sanda 2, http://www.freeimages.com/photo/799970 BY NC ND
THE CHEMISTRY OF WILD GARLIC
Spring is in the air, and if you venture to a forest, so too is the smell of wild garlic. Here's a quick look at the chemistry of this common forest plant.
WILD GARLIC'S SMELL & COMPOSITION
O NH2 O NH2 O NH2

S OH S OH S OH
H3C
O O O
METHIIN ALLIIN ISOALLIIN
The smell of wild garlic stems from the presence of sulfur-containing

compounds called sulfoxides. Wild garlic contains a mix of methiin, alliin,
and isoalliin. These compounds can be further broken down to give volatile
thiosulfinate compounds, including allicin and methyl allyl thiosulfinate, as
CASES OF MISTAKEN IDENTITY
well as a range of others that contribute to the garlic odour.
O O
O
O O
O O CONVALLATOXIN
O
OH O
H O
S S HO OH
S H3C S H OH
COLCHICINE O N
H
O O
OH
ALLICIN METHYL-ALLYL THIOSULFINATE
Other plants can be mistaken for wild garlic. These include lily of the valley,
These breakdown compounds are produced by the plant as a consequence and the leaves of the autumn crocus. Lily of the valley contains a number
of mechanical damage. They serve an antimicrobial role; studies have of compounds known as cardiac glycosides, such as convallatoxin; autumn
shown that allicin shows inhibitory activity against both bacteria and fungi. crocus leaves contain poisonous alkaloids (such as colchicine). Ingesting small
Cows fed on wild garlic produce milk that tastes slightly of the plant as a amounts of either can lead to vomiting, diarrhoea, and even death. The leaves
consequence of some of the compounds present. of both of these plants are devoid of wild garlic's characteristic smell.

A GUIDE TO THE MAILLARD REACTION
The Maillard reaction occurs during cooking, and it is responsible for the non-enzymatic browning of foods when cooked. It actually consists of a number
of reactions, and can occur at room temperature, but is optimal between 140-165˚C. The Maillard reaction occurs in three stages, detailed here.
1 The carbonyl group on a sugar reacts with a protein or amino acid’s amino
group, producing an N-substituted glycosylamine.
Classes of Maillard Reaction Products
O
O O
O O
O O
O
N R
R
C C C O
O C C C N
O
N
+
OO C C C
N
OO C C C RR
The Maillard reaction produces hundreds of products; a small subset of these
OO
O
O
O O
O
O contribute to flavour and aroma, some groups of which are described below.
Melanoidins are also formed, brown, polymeric substances which contribute
SUGAR (GLUCOSE) + AMINO GROUP GLYCOSYLAMINE to the colouration of many cooked foods.
(+ WATER)
O
N NH R
The glycosylamine compound generated in the first step isomerises, by
2 undergoing Amadori rearrangement, to give a ketosamine. N
N
N
O O O O
GLYCOSYLAMINE
O O O O
PYRAZINES PYRROLES ALKYLPYRIDINES ACYLPYRIDINES

C C C N
N
N C C C N
N
N
RR RR cooked cereal-like bitter cracker-like
O
O C C C
OO C C C
roasted nutty burnt cereal
O
O
O
O
O
O
O
O toasted astringent
1,2-ENAMINOL AMADORI COMPOUND

O O O
O S
The ketosamine can react in a number of ways to produce a range of
3 different products, which themselves can react further.
N
O
O O
O
CONDITIONS
O FURANONES FURANS OXAZOLES THIOPHENES

CONDITIONS
O O C
C
ALKALINE
sweet meaty green meaty

ACIDIC
C C C C
C
O C O
O C C C C
O
C C O
C
C
caramel burnt nutty roasted
O
O
O
O
O
O
burnt caramel-like sweet
FISSION PRODUCTS REDUCTONES HYDROXYMETHYLFURFURAL

MAPLE SYRUP CHEMISTRY
Maple syrup is the largest commercially produced product derived from tree sap. The sweet
syrup has more constituents than just sugar, however. Here’s a brief look at a small selection.
SUGARS ACIDITY
HO
HO O
HO OH
O O HO
OH
HO O
OH O OH
OH HO
Sucrose is the main sugar in Maple syrup is slightly acidic
maple syrup, making up almost due to the presence of several
70% of its composition. The organic acids. The most
percentages of other sugars abundant of these is malic
are very low by comparison. acid, at around 0.5%.
PHENOLIC COMPOUNDS SOURCE OF COLOUR

HO
HO O
HO
O O
OH
N N N
O
R R R
VANILLIN (ABOVE) HO O EXAMPLE FRAGMENT OF A MELANOIDIN STRUCTURE
AND QUEBECOL (RIGHT) (Melanoidins are brown polymers formed by the Maillard reaction)
Phenolic compounds in maple syrup form from Maple syrup is graded according to its colour.
degradation of lignin in sap, though some, like However, we still don’t know the exact compounds
quebecol, form in the syrup-making process. Some behind its colouration. Maillard reactions,
contribute to the syrup’s flavour, though the exact caramelisation, and formation of polycarbonyl
combination of compounds remains unclear. compounds have all been implicated.

Image: CC BY-NC licence, The Wild Center, https://goo.gl/FmsdFE BY NC ND
THE CHEMISTRY OF BELL PEPPERS
Bell peppers go through a spectrum of colours as they ripen – here we look at the compounds behind their colour, aroma, and flavour.
BELL PEPPER COLOUR CHEMISTRY

R OH
HO
N N
LUTEIN
Mg
OH
N N
O
O
HO
C20H39
O O VIOLAXANTHIN
O
O O
CHLOROPHYLL BELL PEPPER AROMA

CHLOROPHYLL A: R = –CH3
β-CAROTENE
CHLOROPHYLL B: R = –CHO
N OCH3
Chlorophyll, used by plants for photosynthesis, gives bell peppers their

initial green colour. As the pepper ripens, these are decomposed, and a O O
N
range of carotenoid pigments appear. These include lutein, violaxanthin,
and beta-carotene, which give yellow and orange hues. Eventually red
carotenoid pigments including capsanthin and capsorubin appear. These BELL PEPPER PYRAZINE CUCUMBER ALDEHYDE (E)-2-HEXENAL
red pigments are almost exclusively found in peppers.
The aroma of bell peppers also develops as they ripen. In green peppers,
HO
the characteristic smell is largely due to a single chemical, 2-methoxy-3-
O
isobutylpyrazine ("bell pepper pyrazine"). Other minor contributors include
HO
OH
O
OH O
(E,Z)-2,6-nonadienal ("cucumber aldehyde"). The concentrations of most
volatile compounds drop during ripening, with the exception of (E)-2-hexenal
and (E)-2-hexenol, lending a sweeter, fruitier note to the aroma.
CAPSANTHIN CAPSORUBIN

THE CHEMISTRY OF CHERRIES
Cherries are a popular summer fruit, and come in both sour and sweet varieties. Here we look at the chemical differences between the two.
SWEET CHERRIES AND SOUR CHERRIES

OH
OH
HO O+
OH HO O+
OH
O CH3 O
OH OH HO OH OH
O O O
H3C O O O O
HO O OH
OH
OH OH
OH HO OH
HO OH
OH
OH
CYANIDIN-3-O-RUTINOSIDE CYANIDIN-3-GLUCOSYLRUTINOSIDE
POISONOUS PITS
Cherry colour is due to the presence of compounds called anthocyanins. OH

HO
Sweet and sour cherries usually contain both of the compounds shown, OH AMYGDALIN
O
but sweet cherries contain primarily cyanidin-3-o-rutinoside, whereas HO
in sour cherries cyanidin-3-glucosylrutinoside is more abundant. Sour

O HYDROGEN CYANIDE
HO
cherries also contain anthocyanins in greater concentrations. O
BLACK CHERRY RED CHERRY
HO
OH
O
N H C N ~2.7mg/g ~3.9mg/g
O
HO
MALIC ACID Sour: pH 3.1–3.6
OH Sour cherries: 1.2–1.9% Cyanogenic glycosides are found in the seeds of a number of fruits, including
O OH Sweet cherries: 0.7–0.9% Sweet: pH 3.7–4.5 apples and apricots, and cherries are no exception. Their pits contain
amygdalin, a compound which, when broken down during digestion, releases
The tart flavour of sour cherries is due to the presence of a greater poisonous hydrogen cyanide. While a large number of the pits would need
amount of malic acid. They have a titratable acidity of 1.2–1.9% of malic to be eaten by humans to see toxic effects, much less is needed for animals.
acid. Sour cherries also contain less sugar than sweet cherries. Other parts of the cherry tree, including the leaves, are also toxic to animals.

BLACKBERRY CHEMISTRY
Summer may now be past its peak, but blackberry season is now fast approaching. In this
graphic we briefly look at the compounds that give blackberries their purple-black colour.
OH
OH
HO O
O OH
O
HO OH
OH
OH
CYANIDIN 3-GLUCOSIDE
OH
OH
HO O
Pigment compounds called anthocyanins OH

O
give blackberries their purple to black HO
O
OH
colouration. They are a large group of OH
O O
pigments found in a number of other
plants and flowers. O
O O
Cyanidin 3-Glucoside is the predominant
anthocyanin in blackberries, but they HO
also contain cyanidin 3-dioxalylglucoside, O
thought to be unique to blackberries.
CYANIDIN 3-DIOXALYLGLUCOSIDE

BY NC ND
THE CHEMISTRY OF TURMERIC
Tumeric is a spice lauded for its supposed health benefits, and there are also some neat chemistry tricks you can do with it. Here we look at both!
TURMERIC FLUORESCENCE TURMERIC AS AN INDICATOR

O O O O
H H H H O O
H3C CH3
H O C C C H C C C O H
DIKETONE FORM
H C C C C C C C C C H
H H H H H
HO OH
C C H H
C C O OH
H O C C O H
H H
O O
H3C CH3
CURCUMIN KETO-ENOL FORM
HO OH
Curcumin is a key chemical component of turmeric,

and can also make it fluoresce in the right conditions. If Curcumin's chemical structure is subtly different in
turmeric is sprinkled into alcohol whilst illuminated by acidic and alkaline solution. This allows it to be used as
UV light, a bright green-yellow fluorescence can be seen. an indicator. When added to acids, it remains the yellow
Alcohol is used as curcumin is soluble in alcohol but not in colour of turmeric. However, when added to an alkaline
water, and this helps make the fluorescence visible. solution above pH 8, the shift of a hydrogen atom causes
the compound to change colour, giving a red hue.
EXCITED STATES EXCITED STATES EXCITED STATES
TURMERIC HEALTH BENEFITS

VISIBLE LIGHT
UV LIGHT
ANTI
OXIDANT
GROUND STATE GROUND STATE GROUND STATE

? ? ? ?
This fluorescence happens because the electrons in the Anti-inflammatory, anti-oxidant and anti-cancer properties
curcumin molecules absorb the ultraviolet light, causing of curcumin have been observed in animal and laboratory
them to gain energy and move to an excited state. Some studies. However, at present there have been too few
of the extra energy is lost as vibrational energy, and then clinical trials in humans to be able to confirm these effects.
the electrons fall back to the ground state, emitting visible Curcumin is poorly absorbed and rapidly metabolised and
light as they do so. This gives the green-yellow glow. eliminated when eaten, so little reaches our circulation.

THE CHEMISTRY OF POPCORN
POPCORN FLAVOUR & AROMA COMPOUNDS
O O 2-FURFURYLTHIOL
SH
CH3
(E,E)-2,4-DECADIENAL
2-ACETYL-1-PYRROLINE O CH3
Many aroma compounds are given off by freshly prepared

popcorn. Some of the most significant are 2-acetyl-1-
pyrroline (which is a contributor to the roasty, popcorn-
like aroma), (E,E)-2,4-decadienal (which has a fatty, fried
aroma) and 2-furfurylthiol (which in isolation has a roasted
coffee-like aroma). A range of other pyrazine, pyridine, and WHAT MAKES POPCORN POP?
phenol compounds also contribute to flavour and aroma.
O
CH3
2,3-BUTANEDIONE
O
14% HEAT
H3C
O
2,3-PENTANEDIONE H3C
O
CH3
H2O 180˚C
Flavourings added to popcorn can also contribute to
the aroma. For example, butter-flavoured popcorn can The content of popcorn kernels is about 14% water. When the kernels are
include the compounds 2,3-butanedione (diacetyl) heated, this turns into water vapour at water’s boiling point. However, it is
or 2,3-pentanedione. These compounds can cause trapped by the kernel’s shell until the pressure builds up enough to crack
respiratory problems in workers that inhale them while through. The ‘pop’ is due to the escape of this pressurised water vapour,
manufacturing the flavourings – the condition they can rather than the cracking of the kernel’s shell. The molten starch bursts
cause is known as ‘popcorn lung’. through the shell then rapidly cools, giving popcorn its fluffy appearance.

Chemical Concerns
DOES ACRYLAMIDE CAUSE CANCER?
O WHAT IS ACRYLAMIDE AND WHERE IS IT FOUND?
H
H C Acrylamide is a chemical formed by reactions

C that occur when carbohydrate-rich foods are
C N H
cooked at high temperature. Low levels of it are
H H found in foods including roast potatoes, toast,
and potato chips. It’s also found in roasted
coffee beans and in cigarette smoke.
ACRYLAMIDE
HOW DOES ACRYLAMIDE FORM IN FOODS? O

H H O H
H H
When carbohydrate-rich foods are cooked at H N C H C
C C
high temperature (above 120˚C) amino acids C H C O H
can combine with reducing sugars (such as O R

glucose) to form a range of products. The O
H
N
H
amino acid asparagine, combines with sugars to
produce acrylamide. Higher temperatures and
longer cooking times produce more acrylamide. ASPARAGINE REDUCING SUGAR
Acrylamide is classified as a probable human carcinogen; however, the amounts found in food are very low.
MAX. RECOMMENDED
TOASTED BREAD POTATO CRISPS AV. DAILY INTAKE DAILY INTAKE
4.8 MICROGRAMS 12.4 MICROGRAMS 30 MICROGRAMS 195 MICROGRAMS

(assumes 1 slice = 24 grams) (assumes packet = 32.5 grams) (assumes body weight = 75kg) (assumes body weight = 75kg)
O SHOULD I BE WORRIED ABOUT ACRYLAMIDE?
H
H
C
C
H
C
N
H
H
? Dietary levels of acrylamide are a minor concern
for a small increased lifetime risk of cancer.
This is based on animal studies – evidence for
increased risk in humans is currently minimal.
Increases in cancer risk associated with regularly
drinking alcohol or smoking are much higher.
The latest advice recommends cooking foods a
little less brown to reduce acrylamide content.
IN SHORT: ACRYLAMIDE HASN’T BEEN DECISIVELY LINKED TO INCREASED CANCER RISK AT LEVELS FOUND IN COOKED FOODS
MAKING AN INDICATOR FROM RED CABBAGE
The compounds that give red cabbage its colour can be extracted and used as a pH indicator solution. Here we look at the method and the colours!
MAKING THE INDICATOR
ROUGHLY CHOP
THE CABBAGE
BOIL FOR A 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14
FEW MINUTES
ACIDIC pH ALKALINE
O O O O
3 + O
O O O O O O – O O –
O O O O
STRAIN AND O O O O
LET COOL O O O O
RED (pH <3) VIOLET (pH 4–7) BLUE (pH 7–8) YELLOW GREEN (AT pH >8)

4
The red cabbage extract can be used to determine whether substances are acidic or
USE AS AN alkaline. The structures of the anthocyanin pigments which give the red cabbage its colour
INDICATOR! are subtly changed at varying pH. These different structures give a range of colours.

THE CHEMISTRY OF MANGOES
MANGO FLAVOUR & AROMA COMPOUNDS
A large number of compounds contribute to the flavour and the

aroma of mangoes. The cultivar, maturity, and geographical origin
of the mango all influence the compounds present.
270+ VOLATILE COMPOUNDS

DETECTED IN MANGOES
O O
H3C OH H3C O CH3

MANGOES & CONTACT DERMATITIS
O
ETHYL BUTANOATE Possible R groups
CH3 OH
R = (CH2)14CH3
HDMF OH URUSHIOL
R = (CH2)7CH CH(CH2)5CH3
H3C R = (CH2)7CH CHCH2CH CH(CH2)2CH3
γ-OCTALACTONE O
O R and others...
Esters such as ethyl butanoate account for fruity notes in mango Mangoes belong to the same family of plants as poison ivy. Urushiol,
aroma. A major contributor to sweet notes is HDMF (4-hydroxy- a mix of similar organic compounds which are found in poison ivy
2,5-dimethyl-3(2H)-furanone). Lactones such as γ-octalactone and can cause a rash to develop on contact with the skin, can also be
can lend a coconut-like aroma, while terpenes are also found in found in mango skin. This means that some people who are sensitive
significant quantities and make minor contributions. to urushiol get contact dermatitis when chopping or eating mangoes.

THE CHEMISTRY OF BROCCOLI
COOKING COLOUR CHANGES
Like other green vegetables, broccoli’s colour comes from

chlorophyll. Chlorophyll is found within the chloroplasts of
plant cells. What causes this colour to intensify during cooking?
N N
CHLOROPLASTS
Mg SULFORAPHANE AND CANCER
N N OH
O
HO OH S
C S
GLUCORAPHANIN N CH3
CHLOROPHYLL A OH
RO S O
R = C20H39 O O O
O OCH3 H3C O
S N S SULFORAPHANE
O-
O O
Pockets of air in the space between plant cells cause the

green of chlorophyll to be slightly clouded. During cooking Chopping broccoli releases the enzyme myrosinase from cells. This
these gas pockets expand and escape. This makes the green acts on the glucosinolate compound glucoraphanin; one of the
colour intensify. The effect doesn’t last long, however. Cooking products is sulforaphane. Sulforaphane has been investigated due
also causes plant cells to burst, releasing organic acids. to its ability to kill cancerous cells. As myrosinase is heat-sensitive,
Hydrogen ions from these acids react with chlorophyll to form cooking method affects the amount of sulforaphane present.
pheophytins, making the greens less vibrant. Other sulfur compounds give broccoli its odour when cooked.

THE CHEMISTRY OF EGG FLUORESCENCE
EXCITED STATE
2
EXCITED STATE
NH N 1 3
LIGHT
UV
N HN
GROUND STATE GROUND STATE
1 Molecule absorbs UV light
HOOC COOH 2 Loss of some energy (e.g. heat)
PROTOPORPHYRIN IX 3 Energy released as visible light
When a UV light is shone on an egg shell it fluoresces bright

red. This is due to the presence of protoporphyrin IX, which
is a precursor of haemoglobin. It’s also the compound which
gives chicken eggs their brown colour.

Ci Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. Photos © Hannes Hiller (@MicroXtals) BY NC ND
THE CHEMISTRY OF COW’S MILK
MILK’S COMPOSITION WHY IS MILK WHITE?
Milk is an emulsion of fat in water. It is also Milk contains hundreds of types of protein, of
a colloidal suspension of proteins. Other which casein is the main type. The milk proteins
compounds, including lactose and minerals, are form micelles. These micelles scatter light,
fully dissolved in the solution. causing milk to appear white.
WATER 87.5% CASEIN MICELLES

There are several models of casein micelle structure.
FAT 3.9% This diagram shows the supramolecular structure.
PROTEINS 3.4% CASEIN PROTEINS

LACTOSE & MINERALS 5.2% CALCIUM PHOSPHATE CLUSTER
FATS IN MILK LACTOSE & MILK
Droplets of fat in milk have an average size of 3–4 Lactose is a sugar found in milk. People who
micrometres. They consist mainly of triglycerides, are lactose intolerant are unable to digest it.
and also contain fat-soluble vitamins. Lactose can be fermented by microorganisms to
form lactic acid, causing the milk to sour.
H O R TRIGLYCERIDE HO O
OH
DIGESTION GALACTOSE
H C R R = fatty acid molecules HO O GLUCOSE
OH OH
H C O O O
PALMITIC ACID 23.6–31.4% HO FERMENTATION
H3C
OH
H C OLEIC ACID 14.9–22.0% OH OH
OH
STEARIC ACID 10.4–14.6%

H O R LACTOSE LACTIC ACID
MYRISTIC ACID 9.1–11.9%

THE CHEMISTRY OF SPINACH
THE IRON CONTENT OF SPINACH
Compared to many other vegetables, spinach does have a

higher iron content. However, iron in vegetables tends to have
low bioavailability – that is, it is not easily absorbed in the body.
1.7%
ABSORBED
20%
ABSORBED
SPINACH SIRLOIN STEAK
2.6mg per 100g 0.044mg 2.5mg per 100g 0.50mg WHAT CAUSES ‘SPINACH TEETH’?
Sources: USDA food composition database; Scrimshaw (1991)
O O
Low absorption of iron is partly due to polyphenol compounds HO O
2+
in spinach binding iron – not due to its oxalic acid content (as OH Ca O
previously thought). Though it might not be a great source of
iron, it’s a good source of vitamin A in the form of carotenoids. O O
OXALIC ACID CALCIUM OXALATE
Spinach contains high amounts of oxalic acid. When you eat spinach, it
can leave your teeth with a ‘chalky’ feel. This is caused by the oxalic acid
reacting with the calcium ions in the spinach and in your saliva. This
forms poorly soluble calcium oxalate crystals which coat your teeth.
β-CAROTENE – VITAMIN A PRECURSOR

THE CHEMISTRY OF AUBERGINES
THE COLOUR AND TEXTURE OF AUBERGINES
The purple colour of aubergines comes from anthocyanin pigments.

The main anthocyanin present is nasunin, named after the Japanese
name for aubergine (‘nasubi’). It is present as a mix of cis and trans
isomers; the trans isomer is the more stable of the two.
OH
OH
OH
NASUNIN OH
+
HO O
OH
HO O+
OH OH
O
HO O OH
O
HO O OH cis isomer O
OH O
HO O
O
HO O OH
H3C OH OH
O
O
HO
OH
HO O BITTER FLAVOUR AND BROWNING
OH H3C OH
O O
O OH
trans isomer HO
OH OH
O PHENOLIC COMPOUNDS
OH
R OH QUINONES
Aubergines have a spongy texture, caused by many tiny air pockets
between cells. This is why they shrink when cooked, and also soak O
COMPLEX
up cooking oil. The latter can be prevented by pre-cooking or adding POLYPHENOL OXIDASE
BROWN
salt to draw out water into the air pockets, collapsing the structure. OXYGEN
R O POLYMERS
Phenolic compounds cause the bitter flavour of aubergines.

These compounds also explain their browning when cut. Cutting
releases polyphenol oxidase enzyme from cells; it oxidises phenolic
NaCl compounds, leading to the eventual formation of brown polymers.

THE CHEMISTRY OF DECAFFEINATED COFFEE
SOLVENT DECAFFEINATION CO2 DECAFFEINATION WATER DECAFFEINATION
Solvent decaffeination uses solvents Solvent decaffeination removes ‘Swiss water decaffeination’ soaks
to selectively remove caffeine. caffeine but can also remove other beans in hot water to remove
Common solvents are methylene flavour compounds or precursors. caffeine and flavour compounds.
chloride and ethyl acetate. Carbon dioxide is more selective. Caffeine is removed from the water
by filtration but flavour compounds
Cl WATER
remain. The flavour-saturated water
O
removes caffeine from further bean
C WATER
Cl H H3C O CH3 batches without flavour loss.
H
Methylene chloride (left) and ethyl acetate (right)
COFFEE & CAFFEINE
WATER CARBON
SOLVENT FILTER
Temp. WATER WATER
CAFFEINE
A typical cup of coffee contains CO2 FLAVOUR FLAVOUR
between 70 to 140 milligrams of
caffeine. Caffeine can influence
the central nervous system, and Flavour-charged water used to remove
In direct solvent extraction (above)
can lead to sleep problems,
beans are steamed, then soaked in 65˚C caffeine from new batch of coffee beans
restlessness and discomfort.
solvent to remove caffeine, before Pressure
being steamed, dried, and roasted. ‘French water decaffeination’ soaks
O beans in hot water for 24 hours.
CH3
The beans are removed and dried,
H3C N WATER WATER
N and the water is filtered to remove
SOLVENT
CAFFEINE caffeine. The caffeine-free water is
O N N WATER 300 atm BEANS WATER
CAFFEINE added to the dried beans so that
CH3 they reabsorb flavour compounds.
In indirect solvent extraction (above) At high pressure carbon dioxide

There are several processes used beans are soaked in hot water. The dissolves caffeine. The caffeine is WATER DRY
to decaffeinate coffee. In the U.S. water is then mixed with a solvent to removed from the carbon dioxide
CARBON
decaffeination must remove 97% remove caffeine, before flavours in with water so it can be recirculated. WATER FILTER WATER
of the original caffeine content. the water are returned to the beans. The process lasts for up to 12 hours. CAFFEINE
FLAVOUR FLAVOUR

COFFEE CHEMISTRY: ARABICA VS ROBUSTA
ARABICA COFFEE BEANS ROBUSTA COFFEE BEANS
WORLD PRODUCTION WORLD PRODUCTION
ALTITUDE 600–2200m ALTITUDE 0–800m

70% RAIN 1200–2200mm RAIN 2200–3000mm
30%
TEMPERATURE 15–24˚C TEMPERATURE 18–36˚C
O O O O
N
N CAFFEINE CONTENT N
N
N
N CAFFEINE CONTENT N
N
O N
N
1.2–1.5% O N
N
O N
N
2.2–2.7% O N
N
CHLOROGENIC ACID CONTENT 5.5–8.0% CHLOROGENIC ACID CONTENT 7.0–10.0%

LIPID (FAT) CONTENT 15–17% LIPID (FAT) CONTENT 10.5–11.0%
SUGAR (SUCROSE) CONTENT 6.0–9.0% SUGAR (SUCROSE) CONTENT 3.0–7.0%
KEY FLAVOUR COMPOUNDS KEY FLAVOUR COMPOUNDS
CH3 O H3C N CH3 N OH

HO CH3
CH3
H3C OH H3C OH CH3 H3C
CH3
N H3C N OCH3
O O CH3 O
O
O CH3
3,5-DIMETHYL-2- 2,3-DIETHYL-5- 4-ETHYLGUAIACOL
SOTOLON ABHEXON FURANEOL ETHYLPYRAZINE METHYLPYRAZINE
These compounds give the coffee sweet caramel notes These compounds give the coffee spicy, earthy notes
Regions in which arabica is primarily grown
Arabica produces less coffee per hectare than Regions in which robusta is primarily grown Robusta is considered to have a harsher, more
robusta, and is consequently more expensive. It bitter flavour compared to the smoother flavour
is also more susceptible to disease. of arabica. It is often used in blends.
Regions in which arabica and robusta are grown

THE SCIENCE OF MAKING PORRIDGE
WHAT MAKES PORRIDGE THICKEN? WHAT ARE STARCH GRANULES MADE OF?
When oats are added to hot water, intermolecular Starch granules are built up from amylopectin
bonds in the oat starch granules weaken, causing them (approximately 70%) and amylose (approximately 30%).
to swell. The swelling causes the porridge to thicken.
This process is known as gelatinisation.
TEMPERATURE AND PORRIDGE THICKNESS

AMYLOSE AMYLOPECTIN
PORRIDGE THICKNESS
PEAK VISCOSITY
DESTRUCTION OF
STARCH GRANULES
= glucose molecule
START OF GELATINISATION
Another glucose polymer in oats is β-glucan. β-glucans
make up the bulk of oats’ soluble fibre, and have been
60 90 120
shown to decrease blood cholesterol levels.
TEMPERATURE (˚C)
OH OH
If heating of the oat starch granules continues, they
β-GLUCAN HO O O
eventually start to break down and disintegrate. This O O
STRUCTURE HO
breakdown causes a decrease in porridge thickness. OH OH
n m

Ci This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. Photos: www.pushdoctor.co.uk CC-BY-NC licence. BY NC ND
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FOOD INGREDIENTS
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MARCH 14, 2016 | CEN.ACS.ORG | C&EN 33

PeriodicGraphics
C EN.ACS.O RG 32 JU N E 15, 20 15
3
Li Group 1 - The Alkali Metals
Lithium THE GROUP 1 ELEMENTS ARE SHINY, SOFT, AND HIGHLY REACTIVE METALS, NONE OF WHICH OCCUR NATURALLY AS FREE ELEMENTS
ME LT I NG P OI N T S T H E A L K A L I M E TA L S R E A C T W I T H
11 WAT E R T O F O R M
Na M E TA L H Y D R O X I D E S
Sodium
0
Li 200 0
Na 200 0
K 200
LiOH NaOH KOH RbOH CsOH
180.5·C 97.7·C 63.4·C
19
K A L K A L I M E TA L S
Potassium
0
Rb 200 0
Cs 200 0
Fr 200 R E A C T W I T H Na+ Cl- Na+ Cl-
39.5·C 28.4·C 27.0·C
OX YG E N TO F O R M
ME TA L OXI DE S Cl- Na+ Cl- Na+
37 ALL
OF THE A L K A L I M E TA L S
Rb R E A C T W I T H
Na+ Cl- Na+ Cl-
G R O U P 1 M E TA L S
Rubidium K HAVE HALOGENS TO FORM Cl- Na+ Cl- Na+
ONE I O N I C S A LT S
55 VALENCE ELECT RON
U S E S O F T H E A L K A L I M E T A L S
Cs
Caesium
THE REACTIVITY OF THE GROUP 1 METALS
INCREASES DOWN THE GROUP RUBIDIUM
LITHIUM SODIUM POTASSIUM FRANCIUM
87 AS T H E OUT E R E L E C T RON G E TS & CAESIUM
Fr FURTHER FROM THE NUCLEUS ANTI

STREET LAMPS FERTILISERS ATOMIC
DEPRESSANTS RADIOACTIVE
Francium
& B E C OME S E A S I E R TO R E MOVE TABLE SALT SOAPS
CLOCKS
BATTERIES
WWW.COMPOUNDCHEM.COM
2 0 1 3 C OMP OU ND I N T E R E S T - W W W.C OMP OU NDI N T E R E S T.C OM
4
Be Group 2 - The A lk aline Earth Metals
Beryllium THE GROUP 2 ELEMENTS ARE SHINY, SILVERY-WHITE, AND SOMEWHAT REACTIVE METALS, SOME OF WHICH OCCUR NATURALLY AS FREE ELEMENTS
M E LTI NG P OI NTS
E XCE P T
12 T H E A L K A L I N E E A R T H M E TA L S FOR
MAGNESIUM BARIUM CALCIUM R E A C T W I T H W AT E R TO F O R M
Mg
Magnesium
650˚C 725˚C 839˚C M E TA L H Y D R O X I D E S . . .
Be
M (O H) 2 WHICH HAS A
PROTECTIVE
OXIDE L AY ER
PREVENTING
R E A C T I O N
20
Ca
R A D I U M
Calcium RADIUM STRONTIUM BERYLLIUM R E A C T W I T H
700˚C 764˚C 1278˚C
OX Y G E N TO F O R M
M E TA L OXI D E S
38 AL L
OF THE
Sr G R O U P 2 M E TA L S
R A DI U M IS A
RADIOACTIVE
Strontium Ca HAVE
R E A C T W I T H E L E M E N T
W H I C H U S E D TO
HALOGENS TO FO R M
T WO M E TA L H A L I DE S
B E US ED TO MA KE
GLOW IN THE
56 VA L E NC E E L EC T R O NS D A R K P A I N T
Ba USES OF THE ALKALINE EARTH M E TA L S

Barium THE REACTIVITY OF THE GROUP 2 METALS
I NCR E A S ES DOWN THE GROUP
AS THE OUTER ELECTRONS GET
88 F U R TH E R F R OM TH E N U C LE US
BERYLLIUM MAGNESIUM CALCIUM STRONTIUM BARIUM
Ra & B E CO M E E A S I E R TO R E M OV E
EMERALDS ALLOY
WHEELS
BONES FIREWORKS RAT POISON
TELESCOPE BLACKBOARD TREATING GLASSMAKING

Radium MIRRORS FLARES CHALK OSTEOPOROSIS
THEY ARE LESS REACTIVE THAN GROUP 1
5
B Group 3 - The Icosagens
47+28+8512A
Boron EXCEPT FOR BORON, THE GROUP 3 ELEMENTS ARE ALL METALS, KNOWN AS ‘POOR METALS’ DUE TO THEIR LOW MELTING POINTS & HARDNESS
MELTING POINTS
13 BORON IS Other A L U M I N I U M I S
GALLIUM THALLIUM BORON
A METALLOID
Fe
THE THIRD MOST
Al 30˚C 303˚C 2076˚C Al
A B UNDA NT E L E ME NT
Aluminium A N D T H E 8.1% O
IN THE EARTH’ S CRUST
O N L Y Si A N D T H E M O S T
N O N - M E TA L A B U N DA N T M E TA L
31 INDIUM ALUMINIUM IN GROUP 3
Ga 156˚C 660˚C G R O U P 3
Gallium E L E M E N T S 1 GRAM
ALL OF THE R E A C T WI T H
49 GROUP 3 ELEMENTS O X Y G E N
Al HAVE T O F O R M THE AVER AGE
In TH R E E VA LE N C E M E TA L OXI D E S LETHAL DOSE
Indium
E L E C TR O N S FOR THE
81
M 2O 3 TOXIC ELEMENT
G A L L I U M I S S O L I D T H A L L I U M
Tl AT ROOM TEM P E R ATU R E U S E S O F T H E I C O S A G E N S
Thallium BUT IS
L I QUI D AT A L A R GE R R A NGE
113 O F T E M P E R A T U R E S
BORON ALUMINIUM GALLIUM INDIUM THALLIUM
THA N A N Y OTHE R E LE M E N T
Uut GLASSWARE DRINK CANS
ELECTRONIC TOUCH
S O L ID LIQUID GAS RAT POISON
Ununtrium DETERGENT AIRCRAFT COMPONENTS SCREENS
0K 30 3 K 267 6 K 36 0 0 K
BODIES
6
C Group 4 - The Crystallogens
Carbon THE GROUP 4 ELEMENTS ARE A MIX OF METALS, METALLOIDS & NON-METALS, AND SHOW CONSIDERABLE DIVERSITY IN THEIR PROPERTIES
MELTING POINTS S I L I C O N
14
Si
TIN
232˚C
GERMANIUM
937˚C
CARBON
3730˚C
IS THE SECOND
MOST ABUNDANT
112
Sn 114
Sn 115
Sn 116
Sn 117
Sn
10 118
Sn 119
Sn 120
Sn 122
Sn 124
Sn
Silicon ELEMENT IN THE T I N I S T H E E L E M E N T W I T H T H E

EARTH’S CRUST LARGEST NUMBER OF STABLE ISOTOPES
AT
32 THE GROUP FOUR CARBON
Ge
LEAD
327˚C
SILICON
1410˚C 25.7% ELEMENTS
HYDRIDES
FORM
WITH
MAKES UP
Germanium
ALL
H Y D R O
EH 4
G E N
1 8.5%
OF THE OF THE
50 GROUP 4 ELEMENTS T E T R A H A L I D E S HUMAN BODY
Sn Si H A V E WITH HALOGENS IT ALSO FORMS
Tin FOUR EX 4 ORGANIC COMPOUNDS
VALENCE ELECTRONS THE STUDY OF WHICH
A N D A VA R I E T Y O F I S K N O W N A S
82 OXI DES WITH OXYG E N ORGANIC CHEMISTRY
1999
EXPOSURE FLEROVIUM
Pb T O L E A D IS ONE OF THE U S E S O F T H E C R Y S T A L L O G E N S
MAN-MADE
Lead CAN CAUSE ELEMENTS
L E A D P OI S O N I N G DISCOVERED IN
114 T H E N U M B E R O F CARBON SILICON GERMANIUM TIN LEAD
Fl
Flerovium
8 ALLOTROPES OF CARBON
INCLUDING DIAMOND, GRAPHITE
& B UCKMI NSTER FU L L ER I N E
DIAMONDS
CARBON
GLASS
ELECTRONICS
MICROSCOPE &
CAMERA LENSES TIN CANS
RADIATION
SHIELDING
DATING LEADED PETROL

7
N Group 5 - The Pnictogens
Nitrogen THE GROUP 5 ELEMENTS ARE ALL SOLIDS APART FROM NITROGEN, AND ARE A MIX OF NON-METALS, METALLOIDS AND A METAL
78+21+1A
MELTING POINTS
15 NITROGEN BISMUTH ANTIMONY
BISMUTH O
Other
N I T R O G E N I S
-210˚C 271˚C 631˚C IS THE ONLY THE MOST
P 78% A B U N DA N T E L E M E N T
Phosphorus ME TA L L I C N
IN THE EARTH’S ATMOSPHERE
ELEMENT
33
PRESENT T H E P N I C TO G E N S P H O S P H O R U S
PHOSPHORUS ARSENIC
44˚C 603˚C IN GROUP FIVE FO R M P NI C T I DE S C O N T A I N I N G
As
Arsenic
WITH MOST ELEMENTS CALCIUM PHOSPHATE
ALL PNICTOGENS FORM:
C O M P O U N D S
OF THE MA K E U P
51 GROUP 5 ELEMENTS HYDRIDES
P H A V E WI T H HY DRO G E N
Sb OXIDES 70%
Antimony
FIVE
VALENCE ELECTRONS WITH OXYGEN
HALIDES O F H U M A N
WI T H HA LO G E N S B O N E
83 ANCIENT EGYPTIANS
Bi U S E D T H E
U S E S O F T H E P N I C T O G E N S
Bismuth ANTIMONY COMPOUND
CALLED STIBNITE AS
E Y E M A K E - U P
115 NITROGEN PHOSPHORUS ARSENIC ANTIMONY BISMUTH
Uup 0 . 0 6 L E T HA L D O S E EXPLOSIVES SAFETY MATCHES
AMMUNITION
FLAME
RETARDENTS
X-RAY SHIELDS
Ununpentium
GRAMS O F A R S E N I C FERTILISERS SMOKE BOMBS MANUFACTURING
COSMETICS MEDICINES

8
O Group 6 - The Chalcogens
Oxygen THE GROUP 6 ELEMENTS ARE A MIX OF ELECTRONEGATIVE NON-METALS & METALLOIDS COMMONLY ASSOCIATED WITH METAL BEARING MINERALS
MELTING POINTS A L L O F T H E
16 OXYGEN SELENIUM TELLURIUM
ALL OF THE OX YG E N COMP OUNDS O F
SOLID MA K E S U P
S -219˚C 221˚C 450˚C
CHALCOGENS
HYDROGEN WITH
Sulphur
ARE SOFT
AND
65% CHALCOGENS
A R E T O X I C
OF THE
34 DON’TCONDUCT HUMAN BODY O
SULPHUR POLONIUM H E AT W E L L
Se 120˚C 254˚C H H
Selenium
ALLOTROPES
APART FROM WATER
ALL OF THE O X Y G E N SULPHUR
GROUP 6 ELEMENTS NINE TWENTY O X Y G E N
52 HAVE O2 O3 O4 O8 S 2 S3 S4 S8
I S T H E O N LY
Te S G A S E O U S
CHALCOGEN
Tellurium
S I X VA L E N C E
SELENIUM POLONIUM SELENIUM,
ELECTRONS F I VE T W O T E L L U R I UM &
POLONIUM
MAINLY Se8 α-Po & ß-Po A R E A L L
84 ALL THE GROUP 6 ELEMENTS ME TA L LOI D S
Po F O R M - 2 I O N S U S E S O F T H E C H A L C O G E N S
Polonium W H E N R E A C T I N G W I T H
E L E C T R O P O S I T I V E M E TA L S α
116 S UL P H UR DI OXI DE OXYGEN SULPHUR SELENIUM TELLURIUM POLONIUM
Lv REACTS WITH WATER VAPOUR MAKING STEEL GUNPOWDER PHOTOCOPIERS CD-RW DISCS ALPHA PARTICLE
Livermorium
TO FORM SULPHURIC ACID SULPHURIC
GENERATOR
ROCKET FUEL GLASS-MAKING SOLAR PANELS IN RESEARCH
AND CAUSE ACID RAIN ACID
9
F Group 7 - The Halogens
Fluorine GROUP 7 IS THE ONLY GROUP THAT CONTAINS ELEMENTS IN ALL THREE STATES OF MATTER. THEY ARE ALL REACTIVE NON-METALS
THE HYDROFLUORIC ACID

17 IODINE & ASTATINE H A LO G E N S L E ACH ES CA LCIU M FRO M
SOLIDS AT ROOM TEMPERATURE
Cl ALL FORM BONES AND CAN CAUSE
VERY PAINFUL BURNS
Chlorine B R O M I N E D I AT O M I C
LIQUID AT ROOM TEMPERATURE MOLECULES IT ALSO
EXCEPT D I S S O LV E S G L A S S
35 FLUORINE & CHLORINE
GASES AT ROOM TEMPERATURE
FOR
Br A S TAT I N E
THE HA LOGENS THE HALOGENS
Bromine R E A C T W I T H A R E U S E D A S
ALL O X Y G E N T O F O R M OXIDISING AGENTS
OF THE HA LOGE N OXI DE S WHI LS T
53 GROUP 7 ELEMENTS H A L I D E I O N S
I Cl HAVE THE HALOGENS A R E U S E D A S
Iodine S E VE N R E A C T W I T H REDUCING AGENTS
VA L E NC E E L EC T R O NS M E TA L S T O F O R M -
85
M E TA L H A L I D E S F2 I
IONS
T H E R E AC TIVIT Y O F T H E HA LO G EN S
At DECR E A S ES DOWN THE GROUP U S E S O F T H E H A L O G E N S
Astatine A S IT B ECOMES HA R DER TO
A D D A N E L E C T R O N
117 ESTIMATED AMOUNT OF FLUORINE CHLORINE BROMINE IODINE
Uus
Ununseptium 1 GRAM A S TAT I N E
IN THE EARTH’S CRUST
AT A N Y O N E T I M E
TOOTHPASTE
REFRIGERANT
GASES
BLEACH
CHEMICAL
WARFARE
FIRE RETARDANT
MATERIALS
DISINFECTANTS

2
He Group 8 - The Noble Gases
Helium THE GROUP 8 ELEMENTS ARE ALL ODOURLESS, COLOURLESS, MONOATOMIC GASES WITH A VERY LOW CHEMICAL REACTIVITY
BOILING POINTS THE COLOURS IN ‘ NEON’ S I GNS

10 THE
HELIUM ARGON XENON
NOBLE GASES A R E C A U S E D B Y I O N I S E D N O B L E G A S E S
Ne -269˚C -186˚C -107˚C
ARE ALL
Neon
MONOATOMIC He Ne Ar Kr Xe
AND
RARELY FORM
18 COMPOUNDS 1 2 3
R A D O N I S
NEON KRYPTON RADON RADIOACTIVE
Ar -246˚C -152˚C -62˚C
Argon
ALL H He O
75% 23% 1%
AND CAN ENTER
HOMES THROUGH
BASEMENTS AFTER
OF THE
36 GROUP 8 ELEMENTS
R A DI OA C TI VE
Kr Ar HAVE A
HELIUM D E C A Y OF R OC K S
I S T H E BELOW THE EARTH
Krypton FULL OUTER SHELL SECOND MOST
O F E L EC T R O NS 222
54
ABUNDANT ELEMENT
IN THE UNIVERSE
Rn
THE GROUP 8 ELEMENTS ARE
Xe V E R Y U N R E A C T I V E U S E S O F T H E N O B L E G A S E S
Xenon A S THE Y AL R E ADY HAVE A
F U L L VA L E N C E E L E C TR O N S H E L L NEON
-269˚C
86 H E L I UM HA S THE HELIUM NEON ARGON KRYPTON XENON
LOWEST BOILING POINT
Rn OF ALL ELEMENTS IN BALLOONS
NEON LIGHTS MEDICAL LASERS
CAMERA MEDICAL
Radon T H E P E R I O D I C TA B L E REFRIGERANT LIGHT BULBS
FLASHES IMAGING

T h e Tr a n s i t i o n M e t a l s
A LARGE GROUP OF METALS IN THE CENTRE OF THE PERIODIC TABLE, THEY ARE LESS REACTIVE THAN THE GROUP 1 & 2 METALS, AND HAVE HIGH MELTING POINTS & DENSITIES
21 22 23 24 25 26 27 28 29 30
Sc Ti V Cr Mn Fe Co Ni Cu Zn
Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc
39 40 41 42 43 44 45 46 47 48
Y Zr Nb Mo Tc Ru Rh Pd Ag Cd
Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium
72 73 74 75 76 77 78 79 80
Hf Ta W Re Os Ir Pt Au Hg
Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury
3422˚C
TUNGSTEN HAS N THERE ARE T R A N S I T I ON ME TA L S

T H E HI GH E S T THREE MAGNETIC METALS HAVE
MELTING POINT VARIOUS OXIDATION STATES
I RON , COBA LT
O F A NY -3 -2 -1 +1 +2 +3 +4 +5 +6 +7
ME TA L L I C S AND NICKEL M A N G A N E S E H A S
E L E M E N T T E N P O S S I B L E
ME R C URY I S T H E ON LY
TRANSITION METALS FORM L I Q UI D ME TA L AT
R O O M T E M P E R AT U R E
Hg O X I DAT I O N S TAT E S
Co2+ Cr3+ Fe3+ Ni2+ Fe2+ Cu2+ Mn7+ Mn2+ C O P P E R , S I LV E R & G O L D

U N L I K E G R OU P 1 & 2 ME TA L S A R E K NO W N A S T H E
C O L O U R E D TRANSITION METALS CAN FORM C O I N A G E M E T A L S
CO-ORDINATION COMPLEXES
C O M P O U N D S WITH OTHER ATOMS & MOLECULES
Cu Ag Au

T h e L a n t h a n i d e s
ALSO KNOWN AS THE RARE EARTH ELEMENTS, THE LANTHANIDES ARE SILVE R, METALLIC ELEMENTS, AND CAN BE FOUND IN MINE RALS IN THE EARTH’S CRUST
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
Lanthanum Cerium Praseodymium Neodymium Prometheum Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium
THE LANTHANIDES ALL FORM NEODYMIUM ALLOYS

Yb Er Tb Lu Dy Gd Tm Ho
STABLE +3 IONS ARE USED TO MAKE
T H E S T R O NG E S T MA N Y O F T H E L A N T HA N I D E S
THE LANTHANIDES PERMANENT MAGNETS W E R E F O U N D I N
HAVE ELECTRONS IN F OU ND I N LOU D S P E A K E R S M I NE R A L O R E S F R OM
T H E 4 f O R B I TA L AND IN HEADPHONES A M I NE I N T H E VI L L AG E O F
L E A DI NG TO T H E Y T T E R B Y , S W E D E N
LANTHANIDE CONTRACTION SOME LANTHANIDES
YTTE RBIUM, E RBIUM,
ARE USED AS TE RBIUM & YTTRIUM
£ $ € COLOUR PHOSPHORS ARE ALL NAMED
IN SOME TV SCREENS AFTER YTTERBY
PHOSPHORESCENT
E URO P I UM & T E R BI UM
COMPOUNDS ARE USED IN
Eu Eu Ce Tb Gd IN 2010, CHINA
ACCOUNTED FOR
OF GLOBAL RARE EARTH
95%
ANTI-COUNTERFEIT BANK NOTES LANTHANIDES L A N T HA N I DE ELEMENT PRODUCTION
R E AC T WI T H C OMP OU ND S
Pr3+ Nd3+ Pm3+ Sm3+ Tm3+ Ce4+
O X Y G E N ARE USED TO SAMARIUM & COBALT
Eu3+ Dy3+ Eu2+ Tb3+ Ho3+ Er3+ T O G I V E COLOUR A L LOY I S U S E D TO
S E VE R A L O F T H E
OXIDES CERAMICS MA K E T H E MAG NE T S
& G L A S S FOUND I N E L E C T R I C
L A NT HA NI DE S FO R M
C O LOU R E D I O N S Ln2O3 G UI TA R P I C K- U P S
T h e A c t i n i d e s
T H E A C T I N I D E S A R E D E N S E , R A D I O A C T I V E M E TA L S , M A N Y O F W H I C H A R E U N S TA B L E , A N D T H E M A J O R I T Y O F W H I C H A R E M A D E S Y N T H E T I C A L LY
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103

Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
Actinium Thorium Protactinium Uranium Neptunium Plutonium Americium Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium
DATES OF DISCOVERY OF THE ACTINIDES NATURALLY ABUNDANT SYNTHETICALLY PRODUCED
1820 Th U Ac Pa Np Pu Am Cm Bk Cf Es Fm Md Nb Lr 1970
1829 1841 1899 1930 1940 1944 1949 1950 1952 1955 1958 1961
THE ACTINIDES ALL FORM URANIUM & CURIUM
AC TI N I D E S N A M E D A F TE R FA M O U S S CI E NTI S T S
S TA B L E +3 I ONS PLUTONIUM MARIE CURIE
WON NOBEL PRIZE FOR WORK ON RADIOACTIVITY
& ALSO DISCOVERED POLONIUM AND R ADIUM
BERKELIUM IS THE A R E US ED FO R
EINSTEINIUM
R AREST NUCLEAR POWER ALBERT EINSTEIN
Bk
DEVELOPED GENERAL THEORY OF RELATIVITY & WON
N AT U R A L LY THORIUM CAN FORM
NOBEL PRIZE FOR WORK ON PHOTOELECTRIC EFFECT
FERMIUM
OCCU R R ING MORE COVALENT BONDS 14 ENRICO FERMI
EL EMENT THAN ANY OTHER ELEMENT WON NOBEL PRIZE FOR WORK ON RADIOACTIVITY
( N O M O R E T H A N A F E W ATO M S AT & ALSO CONSTRUCTED THE FIRST NUCLEAR REACTOR
A T I M E I N U R A N I U M D E P O S I T S )
THORIUM IS A MENDELEVIUM
DMITRI MENDELEEV
U3+ U4+ U5+ U6+ PYROPHORIC CREATED THE MODERN PERIODIC TABLE & USED IT TO
PREDICT PROPERTIES OF UNDISCOVERED ELEMENTS
Th ELEMENT
S O M E A C T I N I D E S H AV E ( I G N I T E S S P O N TA N E O U S LY I N A I R ) NOBELIUM
OXI DAT I O N S TAT E S ALFRED NOBEL
THE INVENTOR OF DYNAMITE, & LEFT HIS FORTUNE
CURIUM IS SO AFTER HIS DEATH TO FOUND THE NOBEL PRIZES
O F VA R Y I N G C O L O U R S
R ADIOACTIVE LAWRENCIUM
Cm
Pu3+ Pu4+ Pu5+ Pu6+ Pu7+ T H AT I T ERNEST LAWRENCE
GLOWS PURPLE WON A NOBEL PRIZE FOR THE INVENTION OF THE
CYCLOTRON, A TYPE OF PARTICLE ACCELERATOR

T h e Tr a n s a c t i n i d e s
T H E T R A N SACTI NI DE S ARE A L L SYNTH ETIC, RADIOACTIVE EL EMENTS, WHI C H A R E UN STA BL E A ND GE NE R A L LY ON LY E XI ST FOR F R AC T I ON S O F A S E COND
104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Rf Db Sg Bh Hs Mt Ds Rg Cn Uut Fl Uup Lv Uus Uuo
Rutherforfium Dubnium Seaborgium Bohrium Hassium Meitnerium Darmstadtium Roentgenium Copernicium Ununtrium Flerovium Ununpentium Livermorium Ununseptium Ununoctium
DATES OF DISCOVERY OF THE TRANSACTINIDES
1960 Rf Db Sg Bh Mt Hs Ds Rg Cn Fl Lv 2014
1968 1970 1974 1981 1982 1984 1994 1996 1999 2000
THE TRANSACTINIDES ARE ALL E L E ME N T S 1 1 3 , 1 1 5 , 1 1 7 & 1 1 8 RUTHERFORDIUM
TRANSACTINIDES NAMED AFTER FAMOUS SCIENTISTS

R A D I O A C T I V E HAV E Y E T TO HAV E T H E I R ERNEST RUTHERFORD
WON A NOBEL PRIZE FOR WORK ON RADIOACTIVITY
DI S COVE R I E S CON F I R ME D & DEVELOPED THE ORBITAL THEORY OF THE ATOM
COUNT RY O F DI S COVE RY
N A ME S S U C H A S 113 SEABORGIUM
Uut
GLENN SEABORG
4 UNUNOCTIUM 115
5 6
WON A NOBEL PRIZE FOR HIS WORK ON THE SYNTHESIS
Uup & CHEMISTRY OF TEN OF THE TRANSURANIUM ELEMENTS
ARE PLACEHOLDER NAMES 117

Uus BOHRIUM
UNTIL AN OFFICIAL 118 NIELS BOHR
Uuo
I N C LUDE S U S / RU SS I A J OI NT DI S COVE R I E S NAME IS CHOSEN WON A NOBEL PRIZE FOR DEVELOPING THE BOHR MODEL
OF THE ATOM, WITH ELECTRONS ORBITING THE NUCLEUS
MEITNERIUM
2 8 H O U R S Cf Cs LISE MEITNER
WORKED ON RADIOACTIVITY & NUCLEAR PHYSICS, AND WAS
HA L F L I F E O F T H E MO S T PART OF THE TEAM THAT DISCOVERED NUCLEAR FISSION
S TA B L E T R A N S A C T I N I D E T H E T R A N SAC T I NI DE S A R E ROENTGENIUM
I S OTO P E , D U B NI UM - 2 6 8 FORMED BY COLLIDING ATOMS WILHEM RÖNTGEN
WON THE FIRST NOBEL PRIZE IN PHYSICS IN 1901
O F DI F F E R E NT E L E ME NTS FOR HIS DISCOVERY OF X-RAYS (RÖNTGEN RAYS)
MOST T R A N SAC T I NI DE S COPERNICIUM

E X I S T F O R O N L Y E L E ME NTS A B OVE UNUNOC T I UM
A R E P R O P O S E D TO E XI S T B UT A S NICOLAUS COPERNICUS
F R AC T I ON S O F A S E COND Y E T HAV E N O T B E E N D I S C O V E R E D
MATHEMATICIAN & ASTRONOMER WHO FORMULATED
A H E L I OC E N T R I C MODE L O F T H E U NI VE R S E

PERIODICITY: TRENDS IN THE PERIODIC TABLE
KELVIN
ATOMIC RADIUS ANGSTROMS
UNKNOWN MELTING POINT UNKNOWN
0.00-0.50 0-200
0.50-0.75
200-400
0.75-1.00
400-700
1.00-1.25
1.25-1.50 700-1000
1.50-1.75 1000-1500
1.75-2.00 1500-2000
2.00-2.25
2000-3000
2.25-2.60
3000-4000
Atomic radius decreases across a period as nuclear charge increases but shielding effects Metallic bonded and macromolecular substances tend to have high melting points. For both, this
remain approximately constant, resulting in electrons being drawn closer to the nucleus. is due to the fact that the bonds require a lot of energy to break.
Atomic radius increases down a group as valence electrons become increasingly distant from The majority of non-metals have a simple molecular structure. Simple molecular substances have
the nucleus, and shielding also increases. This leads to a increase in atomic radius despite the low melting points as only weak intermolecular forces must be overcome in order to melt them.
increasing nuclear charge down a group. Strength of these is determined by the size of the molecule.
KILOJOULES/MOLE
ELECTRONEGATIVITY PAULING SCALE
UNKNOWN
IONISATION ENERGY UNKNOWN
0.75-1.00 0-500
1.00-1.25 500-600
1.25-1.50 600-700
1.50-1.75 700-800
1.75-2.00 800-1000
2.00-2.50 1000-1500
2.50-3.00 1500-2000
3.00-4.00 2000-2500
Electronegativity is a measure of the tendency of an atom to attract a bonding pair of electrons. The first ionisation energy generally increases from left to right across a period, as the electron
Generally, electronegativity increases moving towards the top right of the Periodic Table. is drawn closer to the nucleus by the increased nuclear charge and becomes harder to remove.
This increase in electronegativity across a period is due to the increased nuclear charge and Electrons in p orbitals are slightly easier to remove than those in s orbitals of the same energy
approximately constant shielding effects resulting in a greater force of attraction to the nucleus level. Paired electrons in the same orbital can lead to repulsion, again making an electron easier
of the atom felt by the bonding electrons. to remove. Both of these factors can lead to lower than expected first ionisation energies.

INTERNATIONAL
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PERIODIC TABLE graphics blog Compound Interest periodicgraphics.
30 C&EN | CEN.ACS.ORG | MAY 6, 2019
030xCENx09718 30 5/1/2019 5:45:31 PM

A TIMELINE OF THE DISCOVERIES OF THE CHEMICAL ELEMENTS
GROUP 1 GROUP 2 GROUP 13 GROUP 14 GROUP 15 GROUP 16 GROUP 17
GROUP 18 TRANSITION METALS LANTHANIDES ACTINIDES TRANSACTINIDES
V 1801 Sg 1974
VANADIUM SEABORGIUM
Nb 1801 Ga 1875 Bh 1981

NIOBIUM GALLIUM BOHRIUM
Ta 1802 Yb 1878 Ar 1894 Pa 1913 Mt 1982

TANTALUM YTTERBIUM ARGON PROTACTINIUM MEITNERIUM
Cu ~7000 ? Mo 1781 Pd 1803 Ho 1878 He 1895 Hf 1923 Hs 1984

COPPER BCE MOLYBDENUM PALLADIUM HOLMIUM HELIUM HAFNIUM HASSIUM
S ~7000 ? Zn 1746 Te 1783 Ce 1803 Tm 1879 Kr 1898 Re 1925 Bk 1949 Ds 1994

SULFUR BCE ZINC TELLURIUM CERIUM THULIUM KRYPTON RHENIUM BERKELIUM DARMSTADTIUM
C ~7000 ? Ni 1751 W 1783 Os 1803 I 1811 La 1839 Sc 1879 Ne 1898 Tc 1937 Cf 1950 Rg 1994
CARBON BCE NICKEL TUNGSTEN OSMIUM IODINE LANTHANUM SCANDIUM NEON TECHNETIUM CALIFORNIUM ROENTGENIUM
Au ~3000 ? Bi 1753 Zr 1789 Ir 1803 Li 1817 Er 1843 Sm 1879 Xe 1898 Fr 1939 Es 1952 Cn 1996
GOLD BCE BISMUTH ZIRCONIUM IRIDIUM LITHIUM ERBIUM SAMARIUM XENON FRANCIUM EINSTEINIUM COPERNICIUM
Ag ~3000 ? Mg 1755 U 1789 Rh 1803 Cd 1817 Tb 1843 Gd 1880 Po 1898 At 1940 Fm 1953 Fl 1998
SILVER BCE MAGNESIUM URANIUM RHODIUM CADMIUM TERBIUM GADOLINIUM POLONIUM ASTATINE FERMIUM FLEROVIUM
Fe ~2500 ? H 1766 Sr 1790 K 1807 Se 1817 Ru 1844 Pr 1885 Ra 1898 Np 1940 Md 1955 Lv 2000
IRON BCE HYDROGEN STRONTIUM POTASSIUM SELENIUM RUTHENIUM PRASEODYMIUM RADIUM NEPTUNIUM MENDELEVIUM LIVERMORIUM
Sn ~2100 ? As 1250 O 1771 Ti 1791 Na 1807 Si 1824 Cs 1860 Nd 1885 Ac 1899 Pu 1940 No 1963 Mc 2004
TIN BCE ARSENIC OXYGEN TITANIUM SODIUM SILICON CAESIUM NEODYMIUM ACTINIUM PLUTONIUM NOBELIUM MOSCOVIUM
Sb ~1600 ? P 1669 N 1772 Y 1794 Ca 1808 Al 1825 Rb 1861 Dy 1886 Rn 1899 Am 1944 Rf 1964 Nh 2004
ANTIMONY BCE PHOSPHORUS NITROGEN YTTRIUM CALCIUM ALUMINIUM RUBIDIUM DYSPROSIUM RADON AMERICIUM RUTHERFORDIUM NIHONIUM
Hg ~1500 ? Pt 1735 Cl 1774 Be 1797 B 1808 Br 1825 Tl 1861 Ge 1886 Eu 1901 Cm 1944 Lr 1965 Og 2006
MERCURY BCE PLATINUM CHLORINE BERYLLIUM BORON BROMINE THALLIUM GERMANIUM EUROPIUM CURIUM LAWRENCIUM OGANESSON
Pb ~1000 ? Co 1735 Mn 1774 Cr 1798 Ba 1808 Th 1829 In 1863 F 1886 Lu 1907 Pm 1945 Db 1968 Ts 2010
LEAD BCE COBALT MANGANESE CHROMIUM BARIUM THORIUM INDIUM FLUORINE LUTETIUM PROMETHIUM DUBNIUM TENNESSINE
10000 BCE – 1 CE 1 CE – 173 5 CE 173 5 CE – 1775 CE 1775 CE – 1800 CE 1800 CE – 1810 CE 1810 CE – 18 30 CE 18 30 CE – 1870 CE 1870 CE – 1890 CE 1890 CE – 1910 CE 1910 CE – 194 5 CE 194 5 CE – 1970 CE 1970 CE – 2020 CE
The years shown for element discoveries subsequent to those elements which were known since antiquity are those in which the element in question was isolated for the first time. The flags identify the country in which the discovery was made, rather than the nationality of the discoverer(s).
© Andy Brunning/Compound Interest 2019 - www.compoundchem.com | Twitter & Instagram: @compoundchem | Facebook: www.facebook.com/compoundchem
THE PERIODIC TABLE OF THE ELEMENTS
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18
-2 5 -26
9.1 2. 2.2 8.
25 9 27 9
-
-
KEY GROUPS OF ELEMENTS
1 2
H He
2 . 20
0. 2 5
0. 31
HYDROGEN Atomic (proton) Number helium
1.008 4.003
13 9 Melting point (˚C) Boiling point (˚C) Group 1 The Alkali Metals Group 16 The Chalcogens 23 8
12 0.0 72 0 .1
-2 5
9.1 2.
25 9
Group 2 The Alkaline Earth Metals Group 17 The Halogens
-
13 4 297 392 4 02 -19 -18 -18 -2 4
0. 5 7 87 0
1 76 7 27 7 0.0 5 .8 8.8 3 .0 9 .7 8 .1 8 .6 6.
18 12 20 35 21 21 21 24 0
H
2 .20
-
-
-
0. 2 5
3 4
Atomic radius (Å) Electronegativity (Pauling) Groups 3-12 The Transition Metals Group 18 The Noble Gases 5 6 7 8 9 10
Li Be Empirical radius, or calculated HYDROGEN

B C N O F Ne
2 . 55
3.4 4
2 .0 4
0.98
3 .0 4
3.98
1 . 57
0. 38
0. 85
0. 50
1. 4 5
0.65
0.60
1. 0 5
0 .7 0
where empirical unavailable 1.008
Lithium BERYLLIUM Group 13 The Icosagens The Lanthanides Boron carbon NITROGEN oxygen fluorine neon
13 9
6.941 9.012 12 0.0 10.811 12.011 14.007 15.999 18.998 20.180
52 4 89 5 80 6 10 6 14 5 13 3 16 0 20 0
0. 2 9. 5 Group 14 The Crystallogens The Actinides 0.6
0. 5 1. 8 First ionisation energy (kJ/mol) Density (g/cm3) 2 .4 87 2.2 02 1. 2 14 1. 4 81 1.7 81 0. 9
g/L at 0˚C for gases,
indicated with grey text
882 10 9 Group 15 The Pnictogens The Transactinides 2 47 326 277 444 -34 -18
.7 9 .9 0.0 0
Relative Atomic Mass 0. 3 0 14 5 .15 .0 . 30 .6 1. 5 .0 9. 3 5 .8
97 65 For radioactive elements, the mass of the 66 14 44 95 10 4 18
-
11 12 most stable isotope is given in brackets 13 14 15 16 17 18
2 . 58
0.93
1. 31
1. 9 0
1 . 61
2 .19
3 .16
1. 2 5
1. 8 0
1. 5 0
1. 0 0
1. 0 0
1. 0 0
0 .7 1
1.10
Sections are greyed out if that property is not known for a particular element
22.990 24.305 26.982 28.086 30.974 32.065 35.453 39.948
49 73 57 78 10 99 12 15
5.8 0. 97 7. 7 1. 74 7. 5 2. 70 6.5 2. 33 12 1. 82 9.6 1. 96 51 3. 21 21 1.7
8
759 14 8 283 328 340 248 206 286 2 92 27 3 256 9 07 240 283 61 4 685 00 58. -15
. 50 .0 42
.0
4 41 6 68 7 10 7 07 2 46 1 38 1 95 7 55 0 85 2 9. 5 .0 .7 6 0 38
.3
3 7.0 .0 1.0 .0 3 80 7. 4 3 .4
63 15 16 19 19 12 15 14 14 10 41 29 81 22 7. 15
9
8
-
-
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
2 . 55
2 .96
0. 82
2 .01
1. 3 6
1. 5 4
3 .0 0
1. 5 5
1. 8 3
1. 8 8
1. 9 0
1. 0 0
1. 6 3
1. 6 6
1. 9 1
1. 8 1
1. 6 5
2 .18
2 . 20
1. 2 5
0. 88
1. 4 0
1. 3 5
1. 4 0
1. 4 0
1. 4 0
1. 3 5
1. 3 5
1. 3 5
1. 3 5
1. 3 0
1. 8 0
1. 6 0
1.15
1.15
1.15
Potassium calcium Scandium Titanium vanadium chromium manganese iron cobalt Nickel Copper zinc Gallium germanium arsenic selenium bromine krypton
39.098 40.078 44.956 47.867 50.942 51.996 54.938 55.845 58.933 58.693 63.546 65.382 69.723 72.640 74.922 78.971 79.904 83.798
41 6 58 63 9 65 65 65 71 76 76 0 73 1 74 2 90 57 0 76 2 94 94 2 11 13
8.8 9. 8 5 8.8 1 0.9 1 2.9 4 7. 3 7 2.5 7 0.4 5.5 6.4 4 8.8 2.2 4.5 3 2 5
0. 8 1. 5 3 .1 2 .9 4.5 6 .1 7.1 7. 4 7. 8 8.9 7.1 8.9 8.9 7.1 5. 9 5. 3 5.7 1.0 4.8 40 3 .1 51 3 .7
688 13 8 293 4 37 474 463 4 26 415 369 296 2 21 767 207 260 16 3 988 18 4 -10
. 30 .0 7.0 2 26 0 55 7 77 4 23 9 57 5 34 0 64 5 55 3 1. 8 0 1.1 .0 6 .6 2 1. 9 2 0.6 5 9. 5 .0 3 .7 .3 1. 8 8 .1
39 77 15 18 24 26 21 23 19 15 96 32 15 23 63 44 11 11
-
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
2 . 20
2 . 28
2 . 20
2 .0 5
2 .6 6
2 .60
0. 82
1. 2 2
1. 3 3
0.95
1. 9 0
1. 9 6
1. 6 0
1. 9 3
1. 6 9
1 .7 8
2 .16
2 .10
2 . 35
2 .0 0
1. 3 5
1. 3 0
1. 3 5
1. 4 0
1. 4 0
1. 4 0
1. 8 0
1. 4 5
1. 4 5
1. 4 5
1. 4 5
1. 5 5
1. 5 5
1. 5 5
1. 6 0
1. 0 8
RUBIDIUM Strontium yttrium ziRconium NIOBIUM molybdenum Technetium ruthenium Rhodium Palladium SILVER Cadmium Indium Tin antimony tellurium iodine xenon
85.468 87.620 88.906 91.224 92.906 95.951 (97.907) 101.072 102.906 106.421 107.868 112.414 114.818 118.711 121.760 127.603 126.904 131.294
40 54 59 64 65 68 70 71 71 80 73 86 55 70 83 86 10 11
3.0 53 9. 5 63 9.9 47 0 .1 51 2 .1 57 4.3 28 2.4 49 0. 2 37 9.7 45 4.4 02 1.0 49 7. 8 65 8.3 31 8.6 31 0.6 69 9. 3 24 94 0
1. 2. 4. 6. 8. 10
. 11 . 12
.
12
.
12
.
10
. 8. 7. 7. 6. 6. 08 4. 70 5. 9
671 16 4 460 545 593 559 501 413 382 297 356 14 7 174 15 6 962 3 37 - 61
8.
50 .0 7.0 0 33 3 17 8 22 0 86 6 33 2 46 0 6 8
5 64 0 .83 .7 4 .0 3 7. 5 9 1. 5 4 4 .0 .0 2 .0 .0 .0 0 .7
72 22 30 34 31 30 24 17 10 38 30 32 27 25 30 71 0
2
-
-
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs Ba Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
2 . 36
2 . 20
2 . 20
2 . 28
2 .54
2 . 33
2 . 20
2 .0 0
2 .0 0
0. 89
1. 3 0
2 .02
1. 5 0
1. 9 0
1. 6 2
0 .7 9
2 .60
1. 3 5
1. 3 5
1. 3 0
1. 3 5
1. 3 5
1. 3 5
1. 2 0
1. 4 5
1. 5 5
1. 5 0
1. 9 0
1. 8 0
1. 9 0
1. 6 0
2 .15
E57-71
CAESIUM Barium Hafnium tantalum Tungsten Rhenium osmium iridium Platinum gold Mercury Thallium lead Bismuth polonium astatine radon
132.905 137.328 178.492 180.948 183.841 186.207 190.233 192.217 195.084 196.967 200.592 204.383 207.210 208.980 (208.982) (209.987) (222.018)
37 8 50 1 65 1 72 5 75 5 75 2 81 1 86 5 86 9 89 2 10 3 58 5 71 4 70 81 0 93 10
8 3
5 .7 1. 8 2.9 3.5 8.5
1 3. 3 8.4
1 6.6 8.8
19.
2 5.8
2 1. 0 4.2
2 2 .6 5. 2
2 2.6 4.4
2 1.0 0 .1
19.
3 07 1 3.5 9. 4
11 .
8 5.6
11 .
3 3.0 9.7 2 .1 9. 2 0 .1 37 9.7
67 7 17 3
.0 0 .0 6 .0 7
27 69
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
0.9 0
0 .7 0
2 .15
E89-103
FRANCIUM RADIUM Rutherfordium dubnium seaborgium bohrium hassium meitnerium Darmstadtium ROENTGENIUM copernicIum NIHONIUM flerovium MOSCOVIUM Livermorium TENNESSINE OGANESSON
(223.020) (226.025) (261.109) (262.114) (266.122) (264.120) (277.000) (268.139) (281.000) (280.000) (285.000) (286.000) (289.000) (289.000) (293.000) (294.000) (294.000)
39 7 50 0 57
3.0 1. 8 9. 3 5. 5 8.9
346 344 3 13 307 300 19 0 15 2 300 3 12 256 260 286 17 3 11 9 340

0.0 4 5 .0 3 5 .0 0 24 4 42 0 72 0 6 .0 9 12 0 56 3 07 7 61 0 29 8 45 0 4 .0 6 52 2
92 79 93 10 10 10 82 13 13 14 14 15 15 82 16
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
1. 2 4
1. 2 5
1. 2 0
1. 2 0
1. 2 2
1. 2 3
1. 2 7
1.10
1.10
1.10
1.13
1.13
1.12
1.14
1.17
1. 8 5
1. 8 5
1. 8 5
1. 8 5
1. 8 5
1. 8 5
1. 8 0
1. 9 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
138.905 140.116 140.908 144.242 (144.000) 150.362 151.964 157.253 158.925 162.500 164.930 167.259 168.934 173.054 174.967
53 53 9 52 0 53 53 54 54 4 59 56 2 57 5 58 58 59 2 60 7 52 4
5 4.4 1 8.6 6 4.5 5 3.4 0 5.8 3.0 1.0 9 9. 3 7 6 .7 3.4 3.5
8 .1 6 .1 6.6 8 .1 6.4 3 .1 7. 0 7. 2 7. 3 7.1 5. 2 7. 9 8. 2 8.5 8 .7 9. 0 9. 3 6.5 9. 8
3 19 47 8 4 02 413 .0 400 322 260 311

50 8 5 5
8 68 7 3 5
1 44 0 9. 4 8 76 7 40 0 6 .0 0.0 0.0 27 7.0 7.0 27
10 17 15 11 63 11 13 98 90 86 15 82 82 16
6
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
1. 3 0
1. 3 8
1. 3 6
1. 2 8
1. 2 8
1. 3 0
1. 3 0
1. 3 0
1. 3 0
1. 3 0
1. 3 0
1. 5 0
1.10
1.13
1. 8 0
1. 8 0
1. 9 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
actinium thorium protactinium uranium neptunium plutonium americium curium berkelium californium einsteinium fermium mendelevium nobelium Lawrencium
(227.028) (232.038) (231.036) (238.029) (237.048) (244.064) (243.061) (247.070) (247.070) (251.080) 252.083 (257.095) (258.098) (259.101) (262.110)
49 60 56 7 59 60 0 58 57 0 57 59 5 60 61 62 63 64 47
8.8 .0
7
8.5 72 8.3 .3 7. 6 .1
0
4.5 .2 1. 4 81 6.4 .0 8 .1 .5
1
8.0 .2 6 .1 .1
0
9. 4 4 7. 2 4.9 1.6 2.8
10 11 . 15 19 20 19. 12 13 13 15 8.8
NOTES: For elements with more than one allotrope, the properties of the most common allotrope are given. Different allotropes may have differing melting points, boiling points, and densities.
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BY NC ND
PERIODIC TABLE OF ELEMENT SCRABBLE SCORES
HYDROGEN
KEY HELIUM
0–9 POINTS
H ELEMENT NAME
He
16 11
HYDROGEN
10–14 POINTS
LITHIUM BERYLLIUM
H ELEMENT SYMBOL BORON CARBON NITROGEN OXYGEN FLUORINE NEON
Li Be 16 15–19 POINTS B C N O F Ne
12 16 7 10 9 17 11 4
POINTS SCORED
SODIUM MAGNESIUM ALUMINIUM SILICON PHOSPHORUS SULFUR CHLORINE ARGON
20+ POINTS
9 14 13 9 20 9 13 6
POTASSIUM CALCIUM SCANDIUM TITANIUM VANADIUM CHROMIUM MANGANESE IRON COBALT NICKEL COPPER ZINC GALLIUM GERMANIUM ARSENIC SELENIUM BROMINE KRYPTON
13 13 13 10 14 17 12 4 10 12 12 15 10 14 9 10 11 16
RUBIDIUM STRONTIUM YTTRIUM ZIRCONIUM NIOBIUM MOLYBDENUM TECHNETIUM RUTHENIUM RHODIUM PALLADIUM SILVER CADMIUM INDIUM TIN ANTIMONY TELLURIUM IODINE XENON
13 11 12 22 11 20 17 14 13 14 9 14 9 3 13 11 7 12
CAESIUM BARIUM HAFNIUM TANTALUM TUNGSTEN RHENIUM OSMIUM IRIDIUM PLATINUM GOLD MERCURY THALLIUM LEAD BISMUTH POLONIUM ASTATINE RADON
Cs Ba La–Lu Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
11 10 15 10 9 12 10 10 12 6 14 13 5 14 12 8 6
FRANCIUM RADIUM RUTHERFORDIUM DUBNIUM SEABORGIUM BOHRIUM HASSIUM MEITNERIUM DARMSTADTIUM ROENTGENIUM COPERNICIUM NIHONIUM FLEROVIUM MOSCOVIUM LIVERMORIUM TENNESSINE OGANESSON
Fr Ra Ac–Lr Rf Db Sg Bh Hs Mt Ds Rg Cp Nh Fl Mc Lv Ts Og
15 9 22 12 15 14 12 14 18 14 19 13 17 18 18 10 10
LANTHANUM CERIUM PRASEODYMIUM NEODYMIUM PROMETHEUM SAMARIUM EUROPIUM GADOLINIUM TERBIUM DYSPROSIUM HOLMIUM ERBIUM THULIUM YTTERBIUM LUTETIUM
14 10 22 17 19 12 12 14 11 18 14 10 12 16 10
ACTINIUM THORIUM PROTACTINIUM URANIUM NEPTUNIUM PLUTONIUM AMERICIUM CURIUM BERKELIUM CALIFORNIUM EINSTEINIUM FERMIUM MENDELEVIUM NOBELIUM LAWRENCIUM
12 12 18 9 13 13 15 10 17 18 13 14 19 12 17
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A PERIODIC TABLE OF REJECTED ELEMENT NAMES
The names of the chemical elements have a wide and complicated history. Some have always borne the same name, but others have
had several suggestions rejected before arriving at their present-day name. This table looks at some of the rejected element names.
1 2
H
HYDROGEN
TABLE COLOUR KEY Hehelium
3 4
ORIGINAL PROPOSED NAME 5 6 7 8 9 10
Li
Lithium
Gl
GLUCINIUM REJECTED SUGGESTED NAME
B
BorACIUM
C
carbon
AzAZOTE
O
oxygen
F
FLUORE
NoNovum
11 12 ERRONEOUS CLAIMED DISCOVERY 13 14 15 16 17 18
SODIUM Magnium Aluminium silicon PHOSPHORUS sulfur chlorine argon
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K
Potassium
Ca
calcium
Gd
GADENIUM
Me
MENACHITE
Pc
PANCHROMIUM
Cr
chromium
Mn
manganese
Feiron
Co
cobalt
Ni
Nickel
Cu
Copper
Zn zinc
Ga
Gallium
Np Pm
Polymnestum
Hs
HESPERISIUM
Mu MURIDE
EoEosium
Neptunium
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb
RUBIDIUM
Sr
Strontium
Lc
LUCIUM
Zr
ziRconium
Cb
Columbium
Eb
Erebodium
Ma
Masurium
Pl
POLINIUM
RhRhodium
Ce
CERESIUM
Ag
SILVER
Ml
MELINUM
In
Indium
Sn Tin
Sb
antimony
Pi
Pilsum
I
iodine
Xexenon
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs
CAESIUM
Pu
PLUTONIUM
E57-71 Ct
CELTIUM
Ta
tantalum
Sc
SCHEELIUM
Np Os
osmium
Ir
iridium
Pt
Platinum
Au gold
Hg
Mercury
Tl
Thallium
Pblead
Bi
Bismuth
Po
polonium
Ah
Anglo-helvetium
NtNITON
NIPPONIUM
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Ct
CATIUM
Mr
MASRIUM
E89-103 Ku
KURCHATOVIUM
Ns
NIELSBOHRIUM
Av
ALVAREZIUM
Bh
BOHRIUM
Hs
hassium
HaHAHNIUM
Ds
Darmstadtium
Rg Cn
copernicum
Uut
Ununtrium
Rs
RUSSIUM
Uup Ls
leosium
Uus Uuo
ununseptium ununoctium
ROENTGENIUM ununpentium
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
La Oc Pr Di Fl Dp Eu Gd Tb Dy Pp Er Tm Ad Cp
lanthanum OCHROITE praseoDIdymium DIdymium FLORENTIUM DECIPIUM europium gadolinium terbium Dysprosium PHILIPPIUM erbium thulium AlDERBARANIUM CASSIOPEIUM
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
Em
EMANIUM
Th
thorium
Bv
BREVIUM
Kl
KLAPROTHIUM
Ao
AUSONIUM
Ex
EXTREMIUM
Pa
PANDEMONIUM
Bs
BASTARDIUM
Md
Mendelevium
Cy Ls
LOSALIUM
Ph
phoenicium
Md
mendelevium
Jo Lr
Lawrencium
CYCLONIUM JOLIOTIUM

THE PERIODIC TABLE’S ENDANGERED ELEMENTS
1 2
H
HYDROGEN
LIMITED AVAILABILITY – FUTURE RISK TO SUPPLY Hehelium
3 4 5 6 7 8 9 10
Li Be RISING THREAT FROM INCREASED USE B C N O F Ne

Lithium BERYLLIUM Boron carbon NITROGEN oxygen fluorine neon
11 12 SERIOUS THREAT IN THE NEXT 100 YEARS 13 14 15 16 17 18
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K
Potassium
Ca
calcium
Sc
Scandium
Ti
Titanium
V
vanadium
Cr
chromium
Mn
manganese
Feiron
Co
cobalt
Ni
Nickel
CuCopper
Zn zinc
Ga
Gallium
Ge
germanium
As
arsenic
Se
selenium
Br
bromine
Kr
krypton
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb
RUBIDIUM
Sr
Strontium
Y
yttrium
Zr
ziRconium
Nb
NIOBIUM
Mo
molybdenum
Tc
Technetium
Ru
ruthenium
Rh
Rhodium
Pd
Palladium
Ag
SILVER
Cd
Cadmium
In
Indium
Sn Tin
Sb
antimony
Te
tellurium
I
iodine
Xexenon
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs
CAESIUM
Ba
Barium
E57-71 Hf
Hafnium
Ta
tantalum
W
Tungsten
Re
Rhenium
Os
osmium
Ir
iridium
Pt
Platinum
Au gold
Hg
Mercury
Tl
Thallium
Pblead
Bi
Bismuth
Po
polonium
At
astatine
Rnradon
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra E89-103 Rf Db Sg Bh Hs Mt Ds Rg Cn Uut Fl Uup Lv Uus Uuo

FRANCIUM RADIUM Rutherfordium dubnium seaborgium bohrium hassium meitnerium Darmstadtium ROENTGENIUM copernicum Ununtrium flerovium ununpentium Livermorium ununseptium ununoctium
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
Ac
actinium
Th
thorium
Pa
protactinium
U
uranium
Np Pu
plutonium
Am
americium
Cm curium
Bk
berkelium
Cf
californium
Es
einsteinium
Fm
fermium
Md
mendelevium
No
nobelium
Lr
Lawrencium
neptunium
SOURCE: CHEMISTRY INNOVATION KNOWLEDGE TRANSFER NETWORK
Produced for the ACS Green Chemistry Institute by Andy Brunning/Compound Interest.
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PERIODIC TABLE: ELEMENT NAME ORIGINS
1 2
Symbol Key Language of Origin Name Source
H He
Table Colour Key

Hydrogen GREEK ANGLO-SAXON HELIUM
Atomic number Element symbol MINERAL
Water-forming Sun
LATIN SPANISH ASTRONOMICAL BODY
1
3
Li
4
Be H
Hydrogen
RUSSIAN
ENGLISH
NORSE
ARABIC
MYTHOLOGY
5
B
6
C
7
N
8
O
9
F
10
Ne
LITHIUM BERYLLIUM BORON CARBON NITROGEN OXYGEN FLUORINE NEON
Water-forming
PERSON
Stone Berylios GERMAN GAELIC Buraq/borax Charcoal Nitre-forming Acid-forming To flow New
Language SWEDISH NONE – FROM NAME PLACE

11 12 Element name Origin/meaning of origin 13 14 15 16 17 18
NaSODIUM
Mg
MAGNESIUM
JAPANESE PROPERTIES
Al
ALUMINIUM
Si
SILICON
P
PHOSPHORUS
S
SULFUR
Cl
CHLORINE
ArARGON
Soda Magnesia Bitter salt Flint Bringer of light Brimstone Greenish-yellow Idle
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K
POTASSIUM
Ca
CALCIUM
Sc
SCANDIUM
Ti
TITANIUM
V
VANADIUM
Cr
CHROMIUM
Mn MANGANESE
Fe IRON
Co COBALT
Ni NICKEL
Cu COPPER
Zn ZINC
GaGALLIUM
Ge
GERMANIUM
AsARSENIC
Se
SELENIUM
Br
BROMINE
Kr
KRYPTON
Potash Lime Scandinavia Titans Vanadis/Freya Colour Magnet Iren Goblin Devil’s copper From Cyprus Zink France/Gaul Germany Orpiment Moon Stench Hidden
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
RbRUBIDIUM
Sr
STRONTIUM
Y
YTTRIUM
Zr
ZIRCONIUM
Nb NIOBIUM
Mo
MOLYBDENUM
Tc
TECHNETIUM
Ru RUTHENIUM
Rh RHODIUM
Pd
PALLADIUM
Ag Cd CADMIUM
InINDIUM
Sn TIN
Sb
ANTIMONY
Te
TELLURIUM
I
IODINE
XeXENON
SILVER
Dark red Strontian Ytterby Gold-like Niobe Lead Artificial Russia Rose-coloured Pallas Soilfur Calamine Indigo Tin Not alone Earth Violet Stranger
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
CsCAESIUM
Ba
BARIUM
E57-71 Hf
HAFNIUM
Ta
TANTALUM
W
TUNGSTEN
Re
RHENIUM
Os
OSMIUM
Ir
IRIDIUM
Pt
PLATINUM
Au GOLD
Hg MERCURY
Tl
THALLIUM
Pb LEAD
Bi
BISMUTH
Po
POLONIUM
At
ASTATINE
Rn RADON
Sky blue Heavy Copenhagen Tantalus Heavy stone Rhine Smell Iris Little silver Gold Mercury Green twig Lead White mass Poland Unstable Radium
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr
FRANCIUM
Ra
RADIUM E89-103 Rf
RUTHERFORDIUM
Db
DUBNIUM
Sg
SEABORGIUM
Bh BOHRIUM
Hs
HASSIUM
Mt
MEITNERIUM
Ds
DARMSTADTIUM
Rg ROENTGENIUM
Cn COPERNICIUM
Nh NIHONIUM
Fl
FLEROVIUM
Mcmoscovium
Lv
LIVERMORIUM
Ts
TENNESSINE
Og
OGANESSON
France Ray Ernest Rutherford Dubna Glenn Seaborg Niels Bohr Hessen Lise Meitner Darmstadt Wilhem Röntgen Copernicus Japan Georgy Flerov Moscow Livermore Lab Tennessee Yuri Oganessian
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
La
LANTHANIUM
Ce CERIUM
Pr
PRASEODYMIUM
Nd NEODYMIUM
Pm PROMETHIUM
Sm SAMARIUM
Eu
EUROPIUM
Gd GADOLINIUM
TbTERBIUM
Dy
DYSPROSIUM
Ho HOLMIUM
ErERBIUM
Tm THULIUM
Yb
YTTERBIUM
Lu
LUTECIUM
Lie hidden Ceres Green twin New twin Prometheus Samarskite Europe Johan Gadolin Ytterby Hard to obtain Holmia Ytterby Thule Ytterby Paris
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
Ac
ACTINIUM
Th
THORIUM
Pa
PROTACTINIUM
U
URANIUM
Np NEPTUNIUM
Pu
PLUTONIUM
Am CmAMERICIUM CURIUM
Bk
BERKELIUM
Cf
CALIFORNIUM
Es
EINSTEINIUM
Fm FERMIUM
Md
MENDELEVIUM
NoNOBELIUM
Lr
LAWRENCIUM
Ray Thor First ray Uranus Neptune Pluto America Marie Curie Berkeley California Albert Einstein Enrico Fermi Dmitri Mendeleev Alfred Nobel Ernest Lawrence
© Andy Brunning – www.compoundchem.com. Produced in collaboration with Prof Mark Lorch, University of Hull.
Ci CHEMUNICATE Shared under a Creative Commons 4.0 Attribution-NoDerivatives-NonCommercial licence. BY NC ND
THE PERIODIC TABLE OF OXIDATION STATES
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18
0 +1 0 +1
–1 –1
+2
–2
+2
–2
1 2
KEY GROUPS
–3
+3
–3
+3
H Atomic (proton) Number

He
–4
+4
–4
+4
HYDROGEN helium
1.008 4.003
–5
+5
–5
+5
+9 +9
+6 0 +1 +6
+8 +7 –1 +8 +7
S BLOCK ELEMENTS
+1
+2
–2
Known oxidation state
1 each s sub-shell contains up to 2 electrons
0 0 0 0 0 0 0 0
–3
+3
+1 +1 +1 +1 +1 +1
H
–1 +1 –1 +1 –1 –1 –1 –1 –1 –1
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
–4
+4
3 4 HYDROGEN P BLOCK ELEMENTS 5 6 7 8 9 10
–3
–3
–3
–3
–3
–3
–3
–3
+3
+3
+3
+3
+3
+3
+3
+3
Li Be 1.008
B C N O F Ne
–5
+5
each p sub-shell contains up to 6 electrons
+1
–4
–4
–4
–4
–4
–4
–4
–4
+9
+4
+4
+4
+4
+4
+4
+4
+4
Common oxidation state +6

Lithium BERYLLIUM +8 +7 Boron carbon NITROGEN oxygen fluorine neon
6.941 9.012
D BLOCK ELEMENTS 10.811 12.011 14.007 15.999 18.998 20.180
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
–5
–5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9
+6 +6 each d sub-shell contains up to 10 electrons +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7
Relative Atomic Mass

–1
0 +1 –1
0 +1 +1 Oxidation state not known For radioactive elements, the mass of the F BLOCK ELEMENTS –1
0 +1 –1
0 +1 –1
0 +1 –1
0 +1 –1
0 +1 –1
0 +1
most stable isotope is given in brackets each f sub-shell contains up to 14 electrons
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
11 12 13 14 15 16 17 18
–3
–3
–3
–3
–3
–3
–3
–3
+3
+3
+3
+3
+3
+3
+3
+3
–4
–4
–4
–4
–4
–4
–4
–4
+4
+4
+4
+4
+4
+4
+4
+4
22.990 24.305 26.982 28.086 30.974 32.065 35.453 39.948
–5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9
+6 +6 +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7
0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1
–1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
39.098 40.078 44.956 47.867 50.942 51.996 54.938 55.845 58.933 58.693 63.546 65.382 69.723 72.640 74.922 78.971 79.904 83.798
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9
+6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7
0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1
–1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1
+2
–2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
–3
Ag
+3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Cd In Sn Sb Te I Xe
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
–4
+4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
85.468 87.620 88.906 91.224 92.906 95.951 (97.907) 101.072 102.906 106.421 107.868 112.414 114.818 118.711 121.760 127.603 126.904 131.294
–5
+5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9
+6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7
0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1
–1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Hg
–3
Cs
–3
Ba
–3
Hf
–3
Ta
–3
W
–3
Re –3
Os Ir
–3
Pt
–3
Au Tl
–3
Pb
–3
Bi
–3
Po
–3
At
–3
Rn
–3
–3
–3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
E57-71
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
132.905 137.328 178.492 180.948 183.841 186.207 190.233 192.217 195.084 196.967 200.592 204.383 207.210 208.980 (208.982) (209.987) (222.018)
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
–5
–5
–5
+5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9
+6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7
0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1
–1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Lv Ts Og
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
Mc
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
E89-103
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
(223.020) (226.025) (261.109) (262.114) (266.122) (264.120) (277.000) (268.139) (281.000) (280.000) (285.000) (284.000) (289.000) (288.000) (293.000) (294.000) (294.000)
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9
+6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7
0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1
–1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
Dy
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
La Ce Pr Nd Pm Sm Eu Gd Tb Ho Er Tm Yb Lu
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
138.905 140.116 140.908 144.242 (144.000) 150.362 151.964 157.253 158.925 162.500 164.930 167.259 168.934 173.054 174.967
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9
+6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7
0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1 0 +1
–1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1 –1
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
+2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
–2
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
–3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
+3
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
–4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
+4
(227.028) (232.038) (231.036) (238.029) (237.048) (244.064) (243.061) (247.070) (247.070) (251.080) 252.083 (257.095) (258.098) (259.101) (262.110)
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
–5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+5
+9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9 +9
+6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6 +6
+8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7 +8 +7

THE PERIODIC TABLE OF THE ELEMENTS
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18
-2 5 -26
9.1 2. 2.2 8.
25 9 27 9
-
-
KEY GROUPS OF ELEMENTS
1 2
H He
2 . 20
0. 2 5
0. 31
HYDROGEN Atomic (proton) Number helium
1.008 4.003
13 9 Melting point (˚C) Boiling point (˚C) s-block elements 23 8
12 0.0 each s sub-shell contains up to 2 electrons 1s 72 0 .1
-2 5
9.1 2.
25 9
2s 2p
-
13 4 297 p-block elements 392 4 02 -19 -18 -18 -2 4
0. 5 7 87 0
1 76 7 27 7 0.0 5 .8 8.8 3 .0 9 .7 8 .1 8 .6 6.
18 12 each p sub-shell contains up to 6 electrons 20 35 21 21 21 24 0
H
2 .20
3s 3p 3d
-
-
-
0. 2 5
3 4 5 6 7 8 9 10
Atomic radius (Å) Electronegativity (Pauling)
Li Be Empirical radius, or calculated HYDROGEN

B C N O F Ne
2 . 55
3.4 4
2 .0 4
3.98
0.98
3 .0 4
1 . 57
d-block elements
0. 38
0. 85
0. 50
1. 4 5
0.65
0.60
1. 0 5
0 .7 0
where empirical unavailable 1.008 4s 4p 4d 4f
each d sub-shell contains up to 10 electrons
Lithium BERYLLIUM 13 Boron carbon NITROGEN oxygen fluorine neon
12 9
6.941 9.012 .0 0.0 5s 5p 5d 5f 10.811 12.011 14.007 15.999 18.998 20.180
52 4 89 5 f-block elements 80 6 10 6 14 5 13 3 16 0 20 0
0. 2 0. 5 9. 5 1. 8 Density (g/cm3) each f sub-shell contains up to 14 electrons 0.6 2 .4 87 2.2 02 1. 2 14 1. 4 81 1.7 81 0. 9
First ionisation energy (kJ/mol) 6s 6p 6d
g/L at 0˚C for gases,
indicated with grey text
882 10 9 Order of filling of orbitals is shown to the right 7s 7p 2 47 326 277 444 -34 -18
.7 9 .9 0.0 0
Relative Atomic Mass 0. 3 0 14 5 .15 .0 . 30 .6 1. 5 .0 9. 3 5 .8
97 65 For radioactive elements, the mass of the 66 14 44 95 10 4 18
-
11 12 most stable isotope is given in brackets 13 14 15 16 17 18
2 . 58
0.93
1. 31
1. 9 0
1 . 61
2 .19
3 .16
1. 2 5
1. 8 0
1. 5 0
1. 0 0
1. 0 0
1. 0 0
0 .7 1
1.10
Sections are greyed out if that property is not known for a particular element
22.990 24.305 26.982 28.086 30.974 32.065 35.453 39.948
49 73 57 78 10 99 12 15
5.8 0. 97 7. 7 1. 74 7. 5 2. 70 6.5 2. 33 12 1. 82 9.6 1. 96 51 3. 21 21 1.7
8
759 14 8 283 328 340 248 206 286 2 92 27 3 256 9 07 240 283 61 4 685 00 58. -15
. 50 .0 42
.0
4 41 6 68 7 10 7 07 2 46 1 38 1 95 7 55 0 85 2 9. 5 .0 .7 6 0 38
.3
3 7.0 .0 1.0 .0 3 80 7. 4 3 .4
63 15 16 19 19 12 15 14 14 10 41 29 81 22 7. 15
9
8
-
-
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
2 . 55
2 .96
0. 82
2 .01
1. 3 6
1. 5 4
3 .0 0
1. 5 5
1. 8 3
1. 8 8
1. 9 0
1. 0 0
1. 6 3
1. 6 6
1. 9 1
1. 8 1
1. 6 5
2 .18
2 . 20
1. 2 5
0. 88
1. 4 0
1. 3 5
1. 4 0
1. 4 0
1. 4 0
1. 3 5
1. 3 5
1. 3 5
1. 3 5
1. 3 0
1. 8 0
1. 6 0
1.15
1.15
1.15
39.098 40.078 44.956 47.867 50.942 51.996 54.938 55.845 58.933 58.693 63.546 65.382 69.723 72.640 74.922 78.971 79.904 83.798
41 6 58 63 9 65 65 65 71 76 76 0 73 1 74 2 90 57 0 76 2 94 94 2 11 13
8.8 9. 8 5 8.8 1 0.9 1 2.9 4 7. 3 7 2.5 7 0.4 5.5 6.4 4 8.8 2.2 4.5 3 2 5
0. 8 1. 5 3 .1 2 .9 4.5 6 .1 7.1 7. 4 7. 8 8.9 7.1 8.9 8.9 7.1 5. 9 5. 3 5.7 1.0 4.8 40 3 .1 51 3 .7
688 13 8 293 4 37 474 463 4 26 415 369 296 2 21 767 207 260 16 3 988 18 4 -10
. 30 .0 7.0 2 26 0 55 7 77 4 23 9 57 5 34 0 64 5 55 3 1. 8 0 1.1 .0 6 .6 2 1. 9 2 0.6 5 9. 5 .0 3 .7 .3 1. 8 8 .1
39 77 15 18 24 26 21 23 19 15 96 32 15 23 63 44 11 11
-
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
2 . 20
2 . 28
2 . 20
2 .0 5
2 .6 6
2 .60
0. 82
1. 2 2
1. 3 3
0.95
1. 9 0
1. 9 6
1. 6 0
1. 9 3
1. 6 9
1 .7 8
2 .16
2 .10
2 . 35
2 .0 0
1. 3 5
1. 3 0
1. 3 5
1. 4 0
1. 4 0
1. 4 0
1. 8 0
1. 4 5
1. 4 5
1. 4 5
1. 4 5
1. 5 5
1. 5 5
1. 5 5
1. 6 0
1. 0 8
85.468 87.620 88.906 91.224 92.906 95.951 (97.907) 101.072 102.906 106.421 107.868 112.414 114.818 118.711 121.760 127.603 126.904 131.294
40 54 59 64 65 68 70 71 71 80 73 86 55 70 83 86 10 11
3.0 53 9. 5 63 9.9 47 0 .1 51 2 .1 57 4.3 28 2.4 49 0. 2 37 9.7 45 4.4 02 1.0 49 7. 8 65 8.3 31 8.6 31 0.6 69 9. 3 24 94 0
1. 2. 4. 6. 8. 10
. 11 . 12
.
12
.
12
.
10
. 8. 7. 7. 6. 6. 08 4. 70 5. 9
671 16 4 460 545 593 559 501 413 382 297 356 14 7 174 15 6 962 3 37 - 61
8.
50 .0 7.0 0 33 3 17 8 22 0 86 6 33 2 46 0 6 8
5 64 0 .83 .7 4 .0 3 7. 5 9 1. 5 4 4 .0 .0 2 .0 .0 .0 0 .7
72 22 30 34 31 30 24 17 10 38 30 32 27 25 30 71 0
2
-
-
55 56 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs Ba Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
2 . 36
2 . 20
2 . 20
2 . 28
2 .54
2 . 33
2 . 20
2 .0 0
2 .0 0
0. 89
1. 3 0
2 .02
1. 5 0
1. 9 0
1. 6 2
0 .7 9
2 .60
1. 3 5
1. 3 5
1. 3 0
1. 3 5
1. 3 5
1. 3 5
1. 2 0
1. 4 5
1. 5 5
1. 5 0
1. 9 0
1. 8 0
1. 9 0
1. 6 0
2 .15
E57-71
132.905 137.328 178.492 180.948 183.841 186.207 190.233 192.217 195.084 196.967 200.592 204.383 207.210 208.980 (208.982) (209.987) (222.018)
37 8 50 1 65 1 72 5 75 5 75 2 81 1 86 5 86 9 89 2 10 3 58 5 71 4 70 81 0 93 10
8 3
5 .7 1. 8 2.9 3.5 8.5
1 3. 3 8.4
1 6.6 8.8
19.
2 5.8
2 1. 0 4.2
2 2 .6 5. 2
2 2.6 4.4
2 1.0 0 .1
19.
3 07 1 3.5 9. 4
11 .
8 5.6
11 .
3 3.0 9.7 2 .1 9. 2 0 .1 37 9.7
67 7 17 3
.0 0 .0 6 .0 7
27 69
87 88 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
0.9 0
0 .7 0
2 .15
E89-103
(223.020) (226.025) (261.109) (262.114) (266.122) (264.120) (277.000) (268.139) (281.000) (280.000) (285.000) (286.000) (289.000) (289.000) (293.000) (294.000) (294.000)
39 7 50 0 57
3.0 1. 8 9. 3 5. 5 8.9
346 344 3 13 307 300 19 0 15 2 300 3 12 256 260 286 17 3 11 9 340

0.0 4 5 .0 3 5 .0 0 24 4 42 0 72 0 6 .0 9 12 0 56 3 07 7 61 0 29 8 45 0 4 .0 6 52 2
92 79 93 10 10 10 82 13 13 14 14 15 15 82 16
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
1. 2 4
1. 2 5
1. 2 0
1. 2 0
1. 2 2
1. 2 3
1. 2 7
1.10
1.10
1.10
1.13
1.13
1.12
1.14
1.17
1. 8 5
1. 8 5
1. 8 5
1. 8 5
1. 8 5
1. 8 5
1. 8 0
1. 9 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
138.905 140.116 140.908 144.242 (144.000) 150.362 151.964 157.253 158.925 162.500 164.930 167.259 168.934 173.054 174.967
53 53 9 52 0 53 53 54 54 4 59 56 2 57 5 58 58 59 2 60 7 52 4
5 4.4 1 8.6 6 4.5 5 3.4 0 5.8 3.0 1.0 9 9. 3 7 6 .7 3.4 3.5
8 .1 6 .1 6.6 8 .1 6.4 3 .1 7. 0 7. 2 7. 3 7.1 5. 2 7. 9 8. 2 8.5 8 .7 9. 0 9. 3 6.5 9. 8
3 19 47 8 4 02 413 .0 400 322 260 311

50 8 5 5
8 68 7 3 5
1 44 0 9. 4 8 76 7 40 0 6 .0 0.0 0.0 27 7.0 7.0 27
10 17 15 11 63 11 13 98 90 86 15 82 82 16
6
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
1. 3 0
1. 3 8
1. 3 6
1. 2 8
1. 2 8
1. 3 0
1. 3 0
1. 3 0
1. 3 0
1. 3 0
1. 3 0
1. 5 0
1.10
1.13
1. 8 0
1. 8 0
1. 9 5
1 .7 5
1 .7 5
1 .7 5
1 .7 5
(227.028) (232.038) (231.036) (238.029) (237.048) (244.064) (243.061) (247.070) (247.070) (251.080) 252.083 (257.095) (258.098) (259.101) (262.110)
49 60 56 7 59 60 0 58 57 0 57 59 5 60 61 62 63 64 47
8.8 .0
7
8.5 72 8.3 .3 7. 6 .1
0
4.5 .2 1. 4 81 6.4 .0 8 .1 .5
1
8.0 .2 6 .1 .1
0
9. 4 4 7. 2 4.9 1.6 2.8
10 11 . 15 19 20 19. 12 13 13 15 8.8
NOTES: For elements with more than one allotrope, the properties of the most common allotrope are given. Different allotropes may have differing melting points, boiling points, and densities.
C © COMPOUND INTEREST 2016 - WWW.COMPOUNDCHEM.COM | This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives International 4.0 licence.
BY NC ND
23
THE MOLE: 6.022 x 10
What is a Mole?
One mole is the amount of a substance
that contains 6.022 x 1023 atoms or
molecules. It is specifically defined
as the number of atoms contained in
12 grams of carbon-12. This is also
known as ‘Avogadro’s Number’ (NA);
it is named after the Italian scientist
Amedeo Avogadro (left), a suggestion
put forward by French scientist Jean
Perrin to recognise Avogadro’s work.
One mole is essential ly

602,214,179,000,000,000,000,000
of something - in chemistry, atoms or molecules
He
Fe O2 Au 4.00g
H2O 55.9g 32.0g NaCl 197g
18.0g 58.4g
Water Iron Oxygen Table Salt Gold Helium
ONE MOLE IS A DIFFERENT MASS FOR DIFFERENT ELEMENTS & COMPOUNDS

This may seem confusing; however, it’s similar to comparing a dozen elephants to a dozen mice.
Although their masses may be very different, you still have a dozen of each!
A mole is often referred to as ‘a chemist’s dozen’

It’s just an easier way TO count LARGE NUMBERS OF ATOMS & MOLECULES
No. OF Moles = Mass (g) ÷ MASS OF 1 MOLE (g)

VSEPR & THE SHAPES OF MOLECULES
A SUMMARY OF THE MOLECULE SHAPES PREDICTED BY VALENCE SHELL ELECTRON PAIR REPULSION THEORY
SHAPE & BOND Using Valence Shell Electron Pair Repulsion Theory
OF
A NG
E
NAM
KEY Shape
LE
VSEPR is a model used to predict shapes of molecules. Electron pairs repel each
other, and adopt an arrangement that minimises repulsion. To find the shape, a Lewis
irs
No.
pa structure can be drawn, or use the following method (assumes single bonds only):
fb
ne
o
o nd
in g & lo 1 Find the number of electrons the central atom normally has in its valence shell.
2 Add one electron for every atom that the central atom is bonded to.
LINE
AR - 180˚ 3 Add or subtract electrons to account for charges if the molecule is charged.
2
electron
pairs
4
5
Divide the number arrived at by two to find the number of electron pairs.
Subtract no. of atoms bonded to the central atom to find no. of lone pairs.
2 b.p. 6 Arrange electron pairs in the correct shape.
PL ANAR - -
BENt ~119˚
NAL Bonding Pairs & Lone Pairs
GO 1
3
20˚
TRI
Lone pairs lie closer to the central atom, and hence repel more
electron than a bonded pair. The order of strengths of repulsion is:
pairs
2 b.
LONE PAIR/LONE PAIR > BONDED PAIR/ LONE PAIR > BONDED PAIR/BONDED PAIR
3 b.p. p. , 1 l .p.
HEDRAL - 109 L PYRAMIDAL - BEN

T - ~104.5˚
Lone Pair Repulsion
TR A NA
4
.5˚
TE
~10
TRIG
7˚
Each lone pair reduces the bond angle by

electron
pairs APPROXIMATELY 2.5 DEGREES
(if there are 4+ electron pairs arranged around the
3 b. 2 b.
4 b.p. p. , 1 l .p. p. , 2 l .p. central atom, ignore repulsions at >90˚ angles)
IPYRAMIDAL - ORSE - <90˚/<1 T-SH

APED - 90˚ LINE
AR - 180˚
LB W H FAILS FOR:
5
A
20˚
90˚/
SA
TRIGON
Isoelectronic
120˚
species
electron
pairs Transition metal
4 b. 3 b. 2 b. compounds
5 b.p. p. , 1 l .p. p. , 2 l .p. p. , 3 l .p.
DRA
TAHE L - 90˚ PYRAMIDAL - E P L A N AR -
T-SH
APED - 90˚ LINE
AR - 180˚
OC RE UAR 9
6
A
SQ
~90
0˚
SQU
electron
pairs
5 b. 4 b. 3 b. 2 b.
6 b.p. p. , 1 l .p. p. , 2 l .p. p. , 3 l .p. p. , 4 l .p.
© COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM | TWITTER: @COMPOUNDCHEM | FACEBOOK.COM/COMPOUNDCHEM

Ci SHARED UNDER A CREATIVE COMMONS AT TRIBUTION-NONCOMMERCIAL-NODERIVATIVES 4.0 INTERNATIONAL LICENCE
BY NC ND
1 2 3 4 5 6 7 8 9 10
A Guide to Laboratory
11 12 13 14
GLASSWARE 15 16 17
18 19 20 21 22 23 24 25 26 27 28 29 30
1 Test tube 6 Round-bottomed flask 11 Schlenk flask 16 Filter funnel 21 Distilling column 26 Chromatography column
2 Boiling Tube 7 Florence flask 12 Straus flask 17 Thistle funnel 22 Claisen flask 27 Graduated cylinder
3 Beaker 8 Kjeldahl Flask 13 Buchner Flask 18 Liebig condenser 23 Soxhlet extractor 28 Graduated pipette
4 Conical/Erlenmeyer flask 9 Pear-shaped flask 14 Separating funnel 19 Graham condenser 24 Gas syringe 29 Volumetric pipette
5 Volumetric flask 10 Retort flask 15 Dropping funnel 20 Friedrichs condenser 25 Thiele tube 30 Burette

CHEMICAL HAZARD SYMBOLS
Chemical hazard symbols are found on some home products, as well as bottles of chemical reagents
in the lab. Here, we take a look at European hazard symbols and the various dangers that they warn of.
ENVIRONMENTAL HAZARD TOXIC GAS UNDER PRESSURE

Indicates substances that are toxic to Indicates life-threatening effects, Container contains pressurised gas.
aquatic organisms, or may cause long in some cases even after limited This may be cold when released, and
lasting environmental effects. They exposure. Any form of ingestion and explosive when heated. Containers
should be disposed of responsibly. skin contact should be avoided. should not be heated.
CORROSIVE EXPLOSIVE FLAMMABLE

May cause burns to skin and damage May explode as a consequence of Flammable when exposed to heat,
to eyes. May also corrode metals. fire, heat, shock or friction. Chemicals fire or sparks, or give off flammable
Avoid skin & eye contact, and do not with this label should be kept away gases when reacting with water.
breathe vapours. from potential ignition sources. Ignition sources should be avoided.
!
CAUTION OXIDISING HEALTH HAZARD
May irritate the skin, or exhibit minor Burns even in the absence of air, and Short or long term exposure could
toxicity. The chemical should be kept can intensify fires in combustible cause serious long term health
away from the skin and the eyes as a materials. Should be kept away from effects. Skin contact and ingestion of
precaution. ignition sources. this chemical should be avoided.

BY NC ND
CONFUSING ELEMENT SYMBOLS EXPLAINED
Most of the chemical symbols for elements in the periodic table make perfect sense; there are a small selection, however, that seem
to bear no relation to their element’s name. Here’s a look at these rogue symbols, along with explanations of the reasons behind them.
GRAPHIC KEY 11
SODIUM – NATRIUM 19
POTASSIUM – KALIUM 26
IRON – FERRUM
Na Arabic – natrun
K Arabic – al qalīy
Fe Latin – ferrum
ELEMENT ATOMIC NO.
11
ELEMENT NAMES Sodium’s Latin name, ‘natrium’, derives ‘Kalium’ is potassium’s Latin name, and Iron’s Latin name, ‘ferrum’, simply means
Na Source of symbol’s name

from the Greek ‘nítron’ (a name for
sodium carbonate). Its original source is
derives from the Arabic ‘al qalīy’, meaning
“calcined ashes” (the ashes left over when
‘iron’ or ‘sword’, and is possibly of Semitic
origin. The element is known by a myriad
likely to be the Arabic work ‘natrun’. A plant material is burned). As with sodium, of various names in different languages,
number of modern languages still call the a number of modern languages still refer with some sources suggesting there are
ELEMENT SYMBOL element natrium instead of sodium. to potassium as kalium. over 200 different names for it.
29
COPPER – CUPRUM 47
SILVER – ARGENTUM 50
TIN – STANNUM 51
ANTIMONY – STIBIUM
Cu Greek – kypros
Ag Latin – argentum
Sn Latin – stannum/stagnum
Sb Greek – stíbi
Copper’s Latin name was ‘cyprium’, which The Latin name for silver, ‘argentum’, is Tin’s Latin name, ‘stannum’, may be The Latin ‘stibium’ derives from the
itself comes from ‘kypros’, which is the thought to derive originally from Indo- derived from the Indo-European ‘stag’ Greek word ‘stíbi’, meaning eye paint,
Greek name for Cyprus. The island of European, likely referring to the metal’s (dripping) because tin melts at a low referring to antimony’s use as an ancient
Cyprus was famous centuries ago for its shininess. The country Argentina is named temperature. There’s also speculation it eye cosmetic. This is in turn likely derived
copper reserves. The name was eventually after silver, and is the only country to be could be derived from the Cornish ‘stean’ from Arabic or Egyptian. Few countries
simplified to ‘cuprum’. named after a chemical element. due to Cornwall’s famous tin mines. refer to antimony as stibium today.
74
TUNGSTEN – WOLFRAM 79
GOLD – AURUM 80
MERCURY – HYDRARGYRUM 82
LEAD – PLUMBUM
W German – wolf rahm
Au Latin – aurum
Hg Greek – hydrargyros
Pb Latin – plumbum
Wolfram was named after the mineral The Latin name for gold was ‘aurum’, Mercury’s original Latin name was Lead’s Latin name, ‘plumbum’, likely
it was found in, wolframite. This is from meaning ‘yellow’, derived from the word actually ‘argentum vivum’ (living silver), originally derives from a language pre-
the German ‘wolf rahm’, or ‘wolf’s foam’, ‘aurora’ (‘dawn’). The name ‘gold’, used but Latin later borrowed from the dating Ancient Greek. This Latin name
referring to the amount of tin ‘eaten’ by in Germanic languages, means ‘yellow, Greek ‘hydrargyros’ (liquid silver) to give is also the source of the English words
the metal during its extraction. Wolfram is shining metal’; many other European ‘hydrargyrum’. The original English name ‘plumbing’ and ‘plumber’, due to the
still used in several languages. languages use derivatives of aurum. for the element was ‘quicksilver’. historic use of lead in water pipes.

Words for the element ‘iron’ in 213 languages
Collected by Gábor Lente, University of Debrecen, Hungary

e-mail: lenteg@delfin.klte.hu
URL: http://www.klte.hu/~lenteg/index.html
Some of the words listed here use transcripts.
Afrikaans yster
Alabama ochana
Albanian hekur
Anishinaabe biiwaabik
Arabic ‘h/ adiid’
Aromanian heru
Avestan ayanghaênaca
Basque burdina
Belarusan 0":,2"
Bena ikyuma
Bende ijela
Bengali loha
Bisaya puthaw
Boinen c tak
Bondei chuma
Brahui âhin
Breton houarn
Bulgarian 0,:b2@
Bungu ichuma
Catalan ferro
Catawba dorob
Cebuano puthaw
Cherokee ‘ta-lu-gi-s-gi’
Chinese Mandarin ‘tie’
Chuka cuma
Cornish horn
Croatian ñeljezo
Czech ñelezo
Danish jern
Dawida chuma
Doe chuma
Dutch IJzer
Embu cuma
English iron
Esperanto fero
Estonian raud
Faroese jarn
Finnish rauta
Fipa ichela
French fer
Frisian izer
Galician ferro
German Eisen
Gilbertese monei
Greek F\*0D@H ‘sidiros’
Gusii ekioma, egetange
Gweno minya
Gwere kyoma
Hangaza ichuma
Hawaiian hao
Haya ekyoma
Hebrew ‘barzel’
Hehe ichuma
Hiligaynon salsalon
Hindi lohA
Hungarian vas
Icelandic járn
Ikizu echoma
Indonesian besi
Ingush "\T8
Irish Gaelic iarann
Italian ferro
Japanese ‘tetsu’
Jita echuma
Kamba kyUma
Kami chuma
Kapampangan bacal
Karelian rauta
Karuk áyan
Katcha ndhalele
Kazakh H,<zD
Kerebe echoma
Khakas timîr
Kibosho minya
Kiha ichuuma
Kikuyu kigera
Kilegi echuma
Kimbu ichuma
Kimochi pasi
Kinga ikyoma
Kiseri menya
Kisi lyoma
Kivinza ikyuma
Korean
Kurdish asin
Kuria ikioma
Klallam qbmtb! n
Kutu zuma
Kwere zuma
Lambya ichijela
Langi chuma
Latin ferrum
Latvian dzelzs
Lema ipati
Lithuanian geleñis
Luganda kyuma
Luhyia shibia
Lumasaaba sikyuma, siibyaa, sisiuma
Lungwa ichela
Lusoga ekyuma
Mabia sitali
Macedonian 0,:,2@
Machame minya
Makonde chitale
Malay besi
Malila ishijela
Maltese 2hadid
Mamba chuma
Mambwe ichela
Manda kyo_ma
Maori rino
Maragoli kivya, kichuma
Matengo so_ma
Matumbi kyOma
Mbunga kyuma
Meru minya
Meruimenti ithaga, chuma
Merutig ithaa
Mkuu menya
Mkwaya ekyuma
Mpoto kihano
Mongolian H,<,D ‘temür’
Munyarwand ichyuma, ubutare

Mwera chic_h_ulo
Namwaga ichela
Nata ekyoma
Navajo besh
Ndali ichela
Ndamba lyuma
Ndari ichela
Ndengeleko kiuma
Nepalese phalam
Ngindo chOma
Ngoni kyuma
Ngoreme ekyooma
Nguungule chuma
Norwegian jern
Ntuzu chUma, gIsInza
Nyakyusa ikyuma
Nyamwezi kIsInza
Nyaturucha ichuria
Nyaturuwil ichuma
Nyiha ishijera
Nyiramba ishuka
Occitan fèrre
Pali aya
Pangwa shuma
Pilipino bakal
Pimbwe ichela
Polish óelazo
Portuguese ferro
Potawatomi biwabuk
Quechuan khilla
Romanian Fier
Rotuman ’ia 1
Rufiji kioma
Rukiga obutare
Rundi ikyuma
Rungu fweta
Rungwa ichela
Runyambo echoma
Runyankore ekyoma
Runyoro obutare
Russian 0,:,2@ ‘zhelezo’
Rutooro ekyoma
Saami rouvdi
Saanich ikmcn
Safwa ijela
Sambaa kiama
Samialugwe esibya
Samoan u’amea
Sangu ishoma
Sanskrit ‘ayasaH’ or ‘loha’
Sashi_siz ikyuma
Serbian '&@0
Seri enim
Sherpa ‘cha’
Shubi ichuuma
Siha minya, shuma
Slovak ñelezo
Slovenian ñelezo
Sonjo gexoji
Spanish hierro
Suba ikyoma
Subdovian gelzâ
Sukuma jisinza
Sumbwa syoma
Swahili chuma
Swedish järn
Tagalog bakal
Tarawan biti
Thai
Tharaka ithaga
Tibetan lcags
Turkish demir
Turkmen demir
Ukrainian 2":i2@
Ulwa ayan
Urdu ‘lohaa’
Vietnamese sát
Vunjo menya
Wanda ohela
Wanji kyuma
Warlpiri jitipayini
Welsh haearn
Wolof feer, weñ
Wungu ichuma
Yao chisyano
Yiddish eizn
Zanaki ekyema
Zaramo zuhma
Zigua zuma
Zinza echooma
POLYATOMIC IONS: NAMES, FORMULAE & CHARGES
A polyatomic ion is a charged species consisting of two or more atoms covalently bonded together. Here's a guide to some of the most common examples!
+ – 2– – – 2– –
H
O O O
Cl Cl
H
O
N H C
C
O
C O O O Cr
O C N
H
H
H O O O O
H O
AMMONIUM ACETATE CARBONATE CHLORATE CHLORITE CHROMATE CYANIDE

Formula: NH4+ Formula: C2H3O2– Formula: CO32– Formula: ClO3– Formula: ClO2– Formula: CrO42– Formula: CN–
2– – – – – – –
O O O O O
N
O
Cr
O
Cr
O C H S
O
H O H Cl O N O O
O O O O O O O
O
DICHROMATE HYDROGEN CARBONATE HYDROGEN SULFATE HYDROXIDE HYPOCHLORITE NITRATE NITRITE

Formula: Cr2O72– Formula: HCO3– Formula: HSO4– Formula: OH– Formula: ClO– Formula: NO3– Formula: NO2–
– – 2– 3– 2– 2– 2–
O O O O S
S
Cl Mn O O P S O S
O O O O O O
O O O O O O
O O O O O
PERCHLORATE PERMANGANATE PEROXIDE PHOSPHATE SULFATE SULFITE THIOSULFATE

Formula: ClO4– Formula: MnO4– Formula: O22– Formula: PO43– Formula: SO42– Formula: SO32– Formula: S2O32–

CHEMISTRY TECHNIQUES: TITRATION
Used to determine the concentration of a particular solution, by measuring how much of a solution of known concentration reacts with a known volume of it.
EQUIPMENT USING A PIPETTE FILLING THE BURETTE
BURETTE
PIPETTE
CONICAL FLASK
1 2 3
PIPETTE FILLER
WASH OUT WITH DISTILLED Fill USING PIPETTE FILLER, SLOWLY DRAIN LIQUID INTO FILL THE BURETTE ABOVE THE ZERO MARK, ALLOW SOME OF THE SOLUTION THROUGH
WATER THEN THE SOLUTION UNTIL BOTTOM OF MENISCUS FLASK; TOUCH TIP TO WALL THEN DRAIN UNTIL THE BOTTOM OF THE THE BURETTE'S TAP SO THAT THE AREA
INDICATOR 25ml
TO BE USED IS LEVEL WITH LINE TO REMOVE HANGING DROPS MENISCUS IS LEVEL WITH THE ZERO MARK UNDER THE TAP ALSO CONTAINS SOLUTION
25ml
The pipette comes in a Pipettes should never be filled direct from stock bottles As with the pipette, the burette should be rinsed with
range of fixed volumes, or in of solution as this could contaminate them. Instead, fill distilled water then the solution it is to be filled with
graduated form, depending them from some of the solution poured into a beaker. before filling. It is necessary that the area under the tap
on the volume you need to They're calibrated to allow for a small amount of solution also contains solution as the burette's scale includes this
measure. Burettes usually remaining in the tip after the correct volume has been volume. Without doing this, the volume recorded for
hold 50 cm3 of solution. delivered, so this remainder shouldn't be forced out. titrations would be higher than the actual value.
USING INDICATORS CARRYING OUT THE TITRATION CARRYING OUT CALCULATIONS

0 2 4 6 pH 8 10 12 14
TITRATE UNTIL
ROUGH
20.30 cm3
TITRE 1
20.15 cm3
TITRE 2
20.00 cm3
TITRE 3
20.10 cm3
n = cv
NONE NONE PINK
END POINT
NO. OF MOLES CONCENTRATION VOLUME
PHENOLPHTHALEIN
in moles in moles per decimetre cubed in decimetres cubed (dm3)
= concordant titre values, used to calculate average
(mol/dm3 or mol dm -3) (value in cm3 ÷ 1000)
Average titre = (20.15 cm3 + 20.10cm3) ÷ 2 = 20.13 cm3
Assuming that the concentration of the solution in the burette is known...
RED YELLOW YELLOW
METHYL ORANGE 1 Calculate number of moles of solution added from the burette.
To carry out the titration, the tap of the burette is opened to allow
In acid-base titrations, a range of indicators can be used. These the solution inside to flow into a known volume of the solution in Determine the number of moles of solution in the conical flask
are solutions which change colour at a specific pH, and can be the conical flask. The amount of solution from the burette required 2 using the equation for the reaction and reacting ratios.
used to precisely identify when the neutralisation reaction is to reach the end point is recorded. A rough titration is usually
complete (the end point). Different indicators are suitable for followed by more accurate runs. Multiple titrations are carried out Calculate the concentration of the solution in the conical flask
different acid-base combinations. until concordant titres are obtained (within 0.10 cm3 of each other). 2 by rearranging the equation (c = n ÷ v).

A HISTORY OF THE ATOM: THEORIES AND MODELS
How have our ideas about atoms changed over the years? This graphic looks at atomic models and how they developed.
SOLID SPHERE MODEL PLUM PUDDING MODEL NUCLEAR MODEL PLANETARY MODEL QUANTUM MODEL
JOHN DALTON J.J. THOMSON ERNEST RUTHERFORD NIELS BOHR ERWIN SCHRÖDINGER
1803 1904 1911 1913 1926

Dalton drew upon the Ancient Thomson discovered electrons Rutherford fired positively Bohr modified Rutherford’s Schrödinger stated that
Greek idea of atoms (the word (which he called ‘corpuscles’) in charged alpha particles at a thin model of the atom by stating electrons do not move in set
‘atom’ comes from the Greek atoms in 1897, for which he won sheet of gold foil. Most passed that electrons moved around the paths around the nucleus, but
‘atomos ’ meaning indivisible). a Nobel Prize. He subsequently through with little deflection, but nucleus in orbits of fixed sizes in waves. It is impossible to
His theory stated that atoms produced the ‘plum pudding’ some deflected at large angles. and energies. Electron energy know the exact location of the
are indivisible, those of a given model of the atom. It shows the This was only possible if the atom in this model was quantised; electrons; instead, we have
element are identical, and atom as composed of electrons was mostly empty space, with electrons could not occupy ‘clouds of probability’ called
compounds are combinations of scattered throughout a spherical the positive charge concentrated values of energy between the orbitals, in which we are more
different types of atoms. cloud of positive charge. in the centre: the nucleus. fixed energy levels. likely to find an electron.
RECOGNISED ATOMS OF A PARTICULAR RECOGNISED ELECTRONS AS PROPOSED STABLE ELECTRON ORBITS; SHOWS ELECTRONS DON’T MOVE AROUND
REALISED POSITIVE CHARGE WAS EXPLAINED THE EMISSION SPECTRA OF THE NUCLEUS IN ORBITS, BUT IN CLOUDS
ELEMENT DIFFER FROM OTHER ELEMENTS COMPONENTS OF ATOMS LOCALISED IN THE NUCLEUS OF AN ATOM SOME ELEMENTS WHERE THEIR POSITION IS UNCERTAIN
ATOMS AREN’T INDIVISIBLE – THEY’RE No NUCLEUS; DIDN’T EXPLAIN LATER DID NOT EXPLAIN WHY ELECTRONS MOVING ELECTRONS SHOULD EMIT ENERGY
AND COLLAPSE INTO THE NUCLEUS; MODEL STILL WIDELY ACCEPTED AS THE MOST
COMPOSED FROM SUBATOMIC PARTICLES EXPERIMENTAL OBSERVATIONS REMAIN IN ORBIT AROUND THE NUCLEUS ACCURATE MODEL OF THE ATOM
DID NOT WORK WELL FOR HEAVIER ATOMS

WHAT’S CHEMISTRY EVER DONE FOR US?
Science plays a vital role in our health, safety, economies, and governments. Here are just some of the ways chemistry impacts your everyday life.
ANAESTHETICS ANTIBIOTICS BATTERIES BIRTH CONTROL CATALYTIC CONVERTERS

H H
H H R H
C H O H C C N H H H Rh Pt Pd
H H S H
C C O C C C H
Li
H H C
H
C N H
CH
C
O H
C O H
We take surgery under anaesthesia Bacterial infections were a common Both alkaline batteries and the The first oral contraceptives Catalytic converters, developed in
for granted today, but the first cause of death until antibiotics lithium batteries in your phone became available in the 1960s the 1960s and 70s, convert toxic
anaesthetics were only discovered became available the 1930s. were developed by chemists, and after chemists developed synthetic gases and pollutants in car exhaust
in the mid-1800s. Subsequently Chemists have since discovered they’re still working on making compounds that could affect gas into less harmful emissions,
chemists have made many more. numerous classes of antibiotics. improvements to them. hormone levels in the body. helping to reduce pollution.
FERTILISERS FUELS PLASTICS SCREENS WATER TREATMENT

H H
C C
H H
H H
N2 + 3H2 2NH3 C C
Cl Cl
H H
n
The Haber process, developed in Petrol and diesel extracted from Plastics are everywhere in our If you’re reading this on a screen, Water chlorination began in the
the early 1900s, creates 450 million crude oil currently fuel the majority day-to-day lives. Over the years you have chemists to thank. early 1900s and kills bacteria and
tons of nitrogen fertiliser per year. of our cars. Chemists are also chemists have developed a range of Different types of screens and microbes, helping prevent the
This is vital for growing food and investigating cleaner alternatives, plastics for different uses, including touch screens all rely on materials spread of diseases such as cholera.
supporting the world’s population. such as hydrogen fuels. clothing and food packaging. developed by chemists to work. It also keeps swimming pools clear!
CAMPHOR TRIPHENYLPHOSPHATE

Periodic Graphics
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24 C&EN | CEN.ACS.ORG | FEBRUARY 20, 2017

THE CHEMISTRY OF BLOOD
Blood is a complex chemical mixture. The chemicals in it dictate its colour, and some also contribute to its characteristic, slightly metallic
odour. Here we take a look at some of these chemicals, as well as examining some of the differences that determine a person’s blood type.
THE COLOUR OF BLOOD BLOOD TYPES
Haemoglobin is a protein found in Blood type is determined by the presence of antigens.

blood, built up of smaller sub-units Antigens are found on red blood cell surfaces; they can bind
N
O2
N containing ‘haems’. These haems to antibodies and stimulate an immune response. Antibodies
Fe contain iron, and their structure are proteins in blood plasma that help fight infection.
N N gives our blood its red colour when
oxygenated. Deoxygenated blood is a APPROXIMATE WORLDWIDE DISTRIBUTIONS OF BLOOD TYPES
red colour – not blue!
Blood lost due to bleeding gradually
Key ANTIGEN ANTIBODY
O OH O OH turns brown, as haemoglobin is oxidised Usually only red blood cells are added in transfusions, so only blood antibodies of the person receiving blood are of concern.
HAEM B
to methaemoglobin.
(oxygenated form) TYPE A+ TYPE A- TYPE AB+ TYPE AB-
A+
31% A-
2.5% AB+
5% AB-
0.5%
THE SMELL OF BLOOD A Rh A B A B A B
B Rh
O
TYPE B+ TYPE B- TYPE O+ TYPE O-
O 15% 1% 42% 3%
B+ B- O+ O-
B Rh B A Rh A A B
TRANS-4,5-EPOXY-(E)-2-DECENAL
A B
The compound that gives human blood its characteristic
metallic odour is trans-4,5-epoxy-(E)-2-decenal. The metallic The antibodies a blood type contains determines what
smell of metals and blood coming into contact with skin is blood can be received in transfusions. Someone with blood
largely due to oct-1-en-3-one, produced due to the reaction containing A antibodies cannot be given blood containing A
between oxidised skin lipids and the iron in haemoglobin. antigens. O can be given to all as it contain no A or B antigens.

THE CHEMISTRY OF MUMMIFICATION
Dressing up as a mummy for Halloween is easy; actually becoming one is a little more complicated. This graphic looks at the chemistry behind embalming.
DRYING THE BODY EMBALMING MATERIALS
Na2CO3 NaHCO3 NaCl Na2SO4 Mummies were bandaged with linen, and after every
layer oils, resins and balms were applied. Compounds
found in mummy wrappings give hints as to some
SODIUM CARBONATE SODIUM BICARBONATE SODIUM CHLORIDE SODIUM SULFATE
substances used, which included coniferous, cedar,
and pistacia resins, beeswax, and bitumen. When
After the organs were removed, the empty cavities dried, these materials formed a water-resistant seal.
were stuffed with natron, a naturally occurring mixture
of sodium carbonate and sodium bicarbonate, and
small quantities of sodium chloride and sodium
sulfate. This caused rapid desiccation of the body and DEHYDROABIETIC ACID
saponification of fats, preventing decomposition.
Derivatives of abietic acid are
common indicators of the
use of coniferous resins in the
H
FILLING BODY CAVITIES HO O
embalming process.
GUAIACOL
CH3
OH
HO CH3
Phenolic compounds found in
H2C
O CH3 some resins, such as cedar oil, have
bactericidal effects and inhibit
OCH3
decomposition.
R
CINNAMALDEHYDE LINALOOL
STERANE (GENERAL STRUCTURE)
Present in cinnamon and cassia Present in cassia and mastic
Compounds called steranes and
hopanes can show whether bitumen
After drying the body could be stuffed with a range of was used during embalming.
materials before embalming. Along with sawdust and
linen, these included myrrh, cinnamon, frankincense,
cassia, mastic resin, and even onions! Some of these The use of bitumen is often linked to the black
substances contained compounds with antimicrobial appearance of some mummies, but this can also be
activity that could aid the preservation of the body. caused by resin degradation products.

THE CHEMISTRY OF FIREWORK COLOURS
RED YELLOW BLUE SILVER

STRONTIUM SALTS
Strontium Nitrate
ORANGE SODIUM SALTS
GREEN COPPER SALTS
Copper (I) Chloride PURPLE WHITE HOT WHITE
Sodium Nitrate BARIUM SALTS MAGNESIUM &
Strontium Carbonate CALCIUM SALTS Sodium Oxalate
Copper Carbonate COMBINE COPPER BURNING METAL
Strontium Sulfate Calcium Carbonate Barium Nitrate Copper Oxide ALUMINIUM Magnesium
Calcium Chloride
Cryolite Barium Carbonate & STRONTIUM Aluminium
Calcium Sulfate Barium Chloride COMPOUNDS Titanium
Barium Chlorate
COLOUR PRODUCERS FUEL OXIDISER BINDER CHLORINE DONOR

Gunpowder Composition
CH2OH CH2OH CH2OH
NO3 - Nitrate
O O O
Sr Ba Cu ClO3 - Chlorate
75% 15% 10% OH OH OH
ClO3 - Chlorate
OH
O O OH
Potassium Nitrate Charcoal Sulfur OH OH OH
n
Ca Na Mg KNO3 C S
- Perchlorate
ClO4 - Perchlorate
ClO4 Dextrin
ENERGY DENSITY
3 MEGAJOULES PER KG (common binder)
Metal compounds which produce Allows firework to burn; Usually nitrates, chlorates or Hold the mixture together; the Chlorine donors help strengthen
an intense colour when burned. gunpowder, (potassium nitrate, perchlorates; required to provide most commonly used is a starch, some colours. Some oxidisers can
Some are listed above. sulfur & charcoal), is often used. oxygen for the combustion of fuel. dextrin, dampened with water. also act as chlorine donors.

FLAME TEST COLOURS
LITHIUM SODIUM POTASSIUM RUBIDIUM CAESIUM CALCIUM

Li+ Na+ K+ Rb+ Cs+ Ca2+

Sr2+ Ba2+ Ra2+ Cu2+ Fe2+/Fe3+ B3+
INDIUM LEAD ARSENIC ANTIMONY SELENIUM ZINC

In3+ Pb2+ As3+ Sb3+/Sb5+ Se2+/Se4+ Zn2+
A flame test is an analytical procedure used by chemists to detect the presence of

particular metal ions, based on the colour of the flame produced. When heated,
the electrons in the metal ion gain energy and can jump into higher energy levels.
Because this is energetically unstable, the electrons tend to fall back down to
where they were before, releasing energy as they do so. This energy is released as
light energy, and as these transitions vary from one metal ion to another, it leads
to the characteristic colours given by each metal ion.

TRANSITION METAL
ION COLOURS
3+ 2+ 3+ 4+ 5+ 2+ 3+ 6+
Transition metals form coloured compounds
and complexes. These colours can vary
depending on the charge on the metal ion,
and the number and type of groups of atoms
(called ligands) attached to the metal ion. In
aqueous solutions, the ions form complexes
with the colours shown to the right.
OH2
H2O OH2 TITANIUM VANADIUM CHROMIUM
Mn+ Ti V Cr
H2O OH2
OH2
HYDRATED TRANSITION METAL ION
Electrons are arranged around the nucleus of

the metal atom in orbitals. Transition metals,
unlike other metals, have partially filled d
orbitals, which can hold up to 10 electrons.
When ligands are present, some d orbitals 2+ 7+ 2+ 3+ 2+ 2+ 2+
become higher in energy than before, and
some become lower. Electrons can then move
between these higher and lower d orbitals by
absorbing a photon of light. This absorption
of light affects the percieved colour of the
compound or complex. The wavelength of the
light absorbed is affected by the size of the
energy gap between the d orbitals, which is
in turn affected by the type of ligand and the
charge on the metal ion. MANGANESE IRON COBALT NICKEL COPPER
Mn Fe Co Ni Cu
TESTING FOR CATIONS: SODIUM HYDROXIDE & AMMONIA PRECIPITATES
SODIUM HYDROXIDE SOLUTION OR AQUEOUS AMMONIA SOLUTION CAN BE ADDED TO SOLUTIONS CONTAINING METAL IONS IN ORDER TO DISCERN THEIR IDENTITY. THE COLOUR
PRECIPITATE FORMED BY THE REACTION CAN BE USED TO DETERMINE THE METAL IDENTITY. IN SOME CASES, THE PRECIPITATE DISSOLVES IN EXCESS NaOH or NH3.
CALCIUM (Ca2+) CHROMIUM (Cr3+) MANGANESE (Mn2+) IRON (Fe2+) IRON (Fe3+)
COBALT (Co2+) NICKEL (Ni2+) COPPER (Cu2+) ZINC (Zn2+) ALUMINIUM (Al3+)

INORGANIC PAINT PIGMENT COMPOUNDS
A number of inorganic compounds can be used as pigments in paints. Many of these compounds are coloured due to the absorption of light
energy by electrons in d orbital subshells, meaning we see colours depending on which wavelengths of light are not absorbed by the compound.
CARBON BLACK CERULEAN BLUE CHROME GREEN COBALT VIOLET CADMIUM ORANGE
Carbon, C Cobalt (II) stannate, Co2SnO4 Chromium (III) oxide, Cr2O3 Cobalt (II) phosphate, Co3(PO4)2 Cadmium sulfoselenide, Cd2SSe
TITANIUM WHITE ULTRAMARINE BLUE VIRIDIAN GREEN CADMIUM YELLOW CADMIUM RED
Titanium dioxide, TiO2 Sulfur-containing sodium silicate, Na 6 Al4 Si6S 4O20 Hydrated chromium oxide, Cr2O3 Cadmium sulfide, CdS Cadmium selenide, CdSe
ANTIMONY WHITE PRUSSIAN BLUE CADMIUM GREEN CHROME YELLOW RED OCHRE
Antimony trioxide, Sb2O3 Ferric hexocyanoferrate, Fe7(CN)18 Cadmium sulfide & chromium (III) oxide Lead chromate, PbCrO4 Iron (III) oxide, Fe2O3
ZINC WHITE COBALT BLUE ZINC YELLOW

Zinc oxide, ZnO Cobalt (II) aluminate, CoAl2O4 Zinc chromate, ZnCrO4

THE CHEMISTRY OF GEMSTONE COLOURS
Gemstone colours stem from their chemical structures, which absorb different wavelengths of light. Their hardness is measured on the Mohs hardness scale (1-10).
PEARL TURQUOISE OPAL JADE PERIDOT GARNET

Formula: CaCO3 Formula: Al6 (PO4) 4 (OH) 8 .4H2O Formula: SiO2 .nH2O Formula: NaAlSi2O6 Formula: Mg2SiO4 Formula: Mg3 Al2 (SiO4) 3
Mohs hardness: 2.5–4.5 Mohs hardness: 5.0–6.0 Mohs hardness: 5.5–6.0 Mohs hardness: 6.5–7.0 Mohs hardness: 6.5–7.0 Mohs hardness: 6.5–7.5
Produced in soft tissue of shelled Colour caused by the presence ‘Play of colours’ caused by Colour from chromium and iron Colour caused by iron 2+ ions Colour caused by iron 2+ ions
molluscs. The thinner the layers of of copper ions coordinated to the interference and diffraction of impurities. The mineral nephrite replacing magnesium ions in replacing magnesium ions in
the pearl, the finer the lustre. hydroxide ions and water. light passing through structure. is also referred to as jade. some locations in the structure. some locations in the structure.
AMETHYST CITRINE TOURMALINE ZIRCON AQUAMARINE EMERALD

Formula: SiO2 Formula: SiO2 Formula: Na3Li3 Al6 (BO3) 3 (SiO3) 6F4 Formula: ZrSiO4 Formula: Be3 Al2 (SiO3) 6 Formula: Be3 Al2 (SiO3) 6
Mohs hardness: 7.0 Mohs hardness: 7.0 Mohs hardness: 7.0–7.5 Mohs hardness: 7.5 Mohs hardness: 7.5–8.0 Mohs hardness: 7.5–8.0
Colour caused by irradiation of iron The yellow colour of citrine is Colour due to manganese Many colours depending on Colour caused by iron 2+/3+ Colour caused by chromium
3+ ions in place of silicon in some due to the presence of either ions replacing lithium and impurities. Colourless forms are ions replacing aluminium ions in ions replacing aluminium in
locations in the structure. aluminium or iron impurities. aluminium ions in some sites. popular diamond substitutes. some locations in the structure. some locations in the structure.
SPINEL TOPAZ ALEXANDRITE RUBY SAPPHIRE DIAMOND

Formula: MgAl2O4 Formula: Al2SiO4 (F,OH)2 Formula: Al2BeO4 Formula: Al2O3 Formula: Al2O3 Formula: Cn
Mohs hardness: 7.5–8.0 Mohs hardness: 8.0 Mohs hardness: 8.5 Mohs hardness: 9.0 Mohs hardness: 9.0 Mohs hardness: 10
A variety of colours are possible, Pure topaz is colourless; blue & Colour caused by chromium ions Colour caused by chromium ions Colour caused by titanium and Colourless; can be faintly coloured
caused by impurities such as iron, brown varieties are caused by replacing aluminium in some sites. replacing aluminium ions in some iron ions replacing aluminium ions by the trapping of nitrogen or
chromium and nickel. atomic level imperfections. Colour varies in different light. locations in the structure. in some locations in the structure. boron atoms in the crystal.

THE CHEMISTRY OF MATCHES
How Matches Work The Match The Match Box
The composition of matches varies depending POTASSIUM CHLORATE The striking surface of safety match boxes
on type, but safety matches are the most KClO3 Main ingredient (45-55%) in heads of contains red phosphorus and an abrasive
commonly used. They contain a strong safety matches. substance. When struck, a small amount of
oxidising agent in the match head, and red white phosphorus is produced, which ignites.
phosphorus in the striking surface. Striking the S
P
S
PHOSPHORUS SESQUISULFIDE
match causes small amounts of the oxidiser S Component in the heads of ‘strike P P P
P P
and phosphorus to combine, and the heat P anywhere’ matches.
generated by the friction of the striking causes P P P P P P
ANTIMONY (III) SULFIDE P P P
them to ignite. Sb2S3 Added to some matches to make
them burn more vigourously. Red Phosphorus (above); White Phosphorus (below)
Prior to the 1900s, white phosphorus was the
active ingredient in most matches, but this Additionally, the matches contain ammonium P P P P
could cause ‘phossy jaw’ and bone disorders, phosphates to prevent ‘afterglow’, glue to bind P P P P P P P P
and was also toxic, so was replaced. materials, and paraffin wax for ease of burning. P P P P
© COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM | TWITTER: @COMPOUNDCHEM | FACEBOOK: facebook.com/compoundchem

BY NC ND
THE CHEMISTRY OF COLOURED GLASS
Glass is coloured in 3 main ways. It can have transition or rare earth metal ions added; it can be due to colloidal particles formed in the glass; or
it can be due to particles which are coloured themselves. This graphic shows some of the typical chemical elements that are used to colour glass.
SODA-LIME GLASS
COMPOSITION
SiO2 70-74%
SILICON DIOXIDE
CaO 10-14%
CALCIUM OXIDE IRON IRON-SULFUR COPPER CHROMIUM NICKEL GOLD COPPER-TIN
2+ 2+ 3+ 2+
Fe Fe-S Cu Cr Ni Au Cu-Sn
Na2O 13-16%
SODIUM OXIDE
Soda-lime glass is the
most common glass
type, making up an
estimated 90% of all
manufactured glass. Its
uses include containers,
windows, bottles, and
drinking glasses. The
above percentages are MANGANESE COBALT URANIUM NEODYMIUM Erbium SELENIUM-CADMIUM CADMIUM
Mn 3+
Co2+
U 4+/5+/6+
Nd 3+ 3+
Er Se-Cd as CdS
a general composition
only; other compounds
These are typical colours, and can be affected by the type of glass as well as the concentration of the colourant.
are also present in
smaller amounts. Combination with other elements and compounds can also have an effect on the final colouration of the glass.

THE METAL REACTIVITY SERIES
Metals can be ordered according to their reactivities; the table below shows a selection of common metals and their
reactivities with water, air, and dilute acids. A more reactive metal will displace a less reactive metal from a compound.
REACTION WITH REACTION WITH REACTION WITH REACTION WITH

METAL NAME & SYMBOL COLD WATER STEAM AIR/OXYGEN DILUTE ACIDS EXTRACTION METHOD
Produces metal hydroxide Produces metal oxide Produces metal oxide Produces metal salt
& hydrogen & hydrogen & hydrogen
POTASSIUM (K) VIOLENT REACTION VIOLENT REACTION REACTS READILY VIOLENT REACTION ELECTROLYSIS OF MOLTEN METAL ORE
SODIUM (Na) STRONG REACTION VIOLENT REACTION REACTS READILY VIOLENT REACTION ELECTROLYSIS OF MOLTEN METAL ORE
CALCIUM (Ca) MODERATE REACTION VIOLENT REACTION REACTS READILY VIOLENT REACTION ELECTROLYSIS OF MOLTEN METAL ORE
LITHIUM (Li) MODERATE REACTION STRONG REACTION REACTS READILY VIGOROUS REACTION ELECTROLYSIS OF MOLTEN METAL ORE
MAGNESIUM (Mg) VERY SLOW REACTION STRONG REACTION SLOW REACTION VIGOROUS REACTION ELECTROLYSIS OF MOLTEN METAL ORE
ALUMINIUM (Al) NO REACTION MODERATE REACTION SLOW REACTION MODERATE REACTION ELECTROLYSIS OF MOLTEN METAL ORE
(Carbon)
ZINC (Zn) NO REACTION MODERATE REACTION REACTS WHEN HEATED MODERATE REACTION C METAL ORE SMELTED WITH CARBON
IRON (Fe) NO REACTION REVERSIBLE REACTION REACTS WHEN HEATED MODERATE REACTION C METAL ORE SMELTED WITH CARBON
NICKEL (Ni) NO REACTION SLOW REACTION REACTS WHEN HEATED SLOW REACTION C METAL ORE SMELTED WITH CARBON
TIN (Sn) NO REACTION NO REACTION REACTS WHEN HEATED SLOW REACTION C METAL ORE SMELTED WITH CARBON
LEAD (Pb) NO REACTION NO REACTION REACTS WHEN HEATED SLOW REACTION C METAL ORE SMELTED WITH CARBON
(Hydrogen)
COPPER (Cu) NO REACTION NO REACTION REACTS WHEN HEATED NO REACTION HEAT OR PHYSICAL EXTRACTION
MERCURY (Hg) NO REACTION NO REACTION REVERSIBLE REACTION NO REACTION HEAT OR PHYSICAL EXTRACTION
SILVER (Ag) NO REACTION NO REACTION NO REACTION NO REACTION HEAT OR PHYSICAL EXTRACTION
GOLD (Au) NO REACTION NO REACTION NO REACTION NO REACTION HEAT OR PHYSICAL EXTRACTION
PLATINUM (Pt) NO REACTION NO REACTION NO REACTION NO REACTION HEAT OR PHYSICAL EXTRACTION
© COMPOUND INTEREST 2015 - www.compoundchem.com | Twitter: @compoundchem

Photos via images-of-elements.com & en.wikipedia.org/wiki/User:Dnn87 BY NC ND
THE CHEMISTRY OF LIMESCALE
Limescale can clog up your kitchen appliances, and build up on your bathroom surfaces. What actually causes this build up? Here’s
a quick look at the chemistry behind limescale formation, chemicals that can help prevent it, and others that help to remove it.
WATER HARDNESS WATER SOFTENERS

IN OUT
CALCIUM IONS SULFATE IONS Na+ Na+ Na+ Na+ O OH
2+ – O O
Ca2+ Na+
Ca2+
2+ Mg 2–
HCO3 Ca2+ Ca2+ Na+ Na+
2+
Ca Na+ HO OH
Ca SO4 Na+ Na+ Na+ Na+ OH
MAGNESIUM IONS BICARBONATE IONS ION EXCHANGE RESIN CITRIC ACID
‘Hard water’ is water which contains a large amount of mineral Appliances such as dishwashers can soften water
ions, most commonly calcium and magnesium ions. Permanent by passing it through an ion exchange resin. This
hard water is mainly due to dissolved calcium and magnesium
exchanges scale-causing metal ions in the water for
sulfates. Temporary hard water is mainly due to dissolved calcium
bicarbonate. Temporary hardness can be removed by boiling the sodium ions. Compounds such as citric acid and sodium
water, but permanent hardness cannot. sesquicarbonate can be used to soften laundry water.
LIMESCALE & SOAP SCUM 2+ 2–

REMOVING LIMESCALE
Ca2+(aq) + 2HCO3–(aq) CaCO3(s) + CO2(aq) + H2O(l) Ca CO3 O
O O
Calcium bicarbonate can decompose when heated to form insoluble

Limescale consists mainly of calcium
OH H2N S OH HO P OH H Cl
calcium carbonate – known in this context as limescale – along OH O OH
with water and carbon dioxide. This process removes the temporary carbonate. It can also contain small
hardness from water that the calcium bicarbonate causes. amounts of the following compounds,
LACTIC ACID SULFAMIC ACID PHOSPHORIC ACID HYDROCHLORIC ACID
depending on water composition:
2(C18H35O2)–(aq) + Mg2+(aq) Mg(C18H35O2)2(s) calcium sulfate

Once limescale has been formed, it can be removed from
barium sulfate
appliances or surfaces by reacting it with an acid. A variety
magnesium hydroxide
Calcium and magnesium ions in the water can also react with the of acids can be used, all of which react with the calcium
calcium phosphate
fatty acids found in soaps to produce insoluble compounds that form carbonate to produce a soluble calcium salt, along with
a soap scum on bathroom surfaces. The example shown above is that zinc phosphate
carbon dioxide and water as side products.
of stearate ions reacting to produce magnesium stearate. iron hydroxides

– 2– – – – – +
O O H
O O
H N
C
C
O
C C H C N N O O
N H
H
H O O O O O O H
H
ACETATE CARBONATE HYDROGEN CARBONATE CYANIDE NITRATE NITRITE AMMONIUM

Formula: C2H3O2– Formula: CO32– Formula: HCO3– Formula: CN– Formula: NO3– Formula: NO2– Formula: NH4+
– 2– 2– 2– – 2– 3–
O O S O
S
O H O O O S S S P
O O O
H
O O
O O O O O
O O O O
HYDROXIDE PEROXIDE SULFITE SULFATE HYDROGEN SULFATE THIOSULFATE PHOSPHATE

Formula: OH– Formula: O22– Formula: SO32– Formula: SO42– Formula: HSO4– Formula: S2O32– Formula: PO43–
– – – – 2– 2– –
O O O
O O
Cl Cl
O
Cl O O O O Cl
O
Cr
O O
Cr
O
Cr
O Mn
O
O O O O O O
O O O
HYPOCHLORITE CHLORITE CHLORATE PERCHLORATE CHROMATE DICHROMATE PERMANGANATE

Formula: ClO– Formula: ClO2– Formula: ClO3– Formula: ClO4– Formula: CrO42– Formula: Cr2O72– Formula: MnO4–

+ – 2– – – 2– –
H
O O O
Cl Cl
H
O
N H C
C
O
C O O O Cr
O C N
H
H
H O O O O
H O
AMMONIUM ACETATE CARBONATE CHLORATE CHLORITE CHROMATE CYANIDE

Formula: NH4+ Formula: C2H3O2– Formula: CO32– Formula: ClO3– Formula: ClO2– Formula: CrO42– Formula: CN–
2– – – – – – –
O O O O O
N
O
Cr
O
Cr
O C H S
O
H O H Cl O N O O
O O O O O O O
O
DICHROMATE HYDROGEN CARBONATE HYDROGEN SULFATE HYDROXIDE HYPOCHLORITE NITRATE NITRITE

Formula: Cr2O72– Formula: HCO3– Formula: HSO4– Formula: OH– Formula: ClO– Formula: NO3– Formula: NO2–
– – 2– 3– 2– 2– 2–
O O O O S
S
Cl Mn O O P S O S
O O O O O O
O O O O O O
O O O O O
PERCHLORATE PERMANGANATE PEROXIDE PHOSPHATE SULFATE SULFITE THIOSULFATE

Formula: ClO4– Formula: MnO4– Formula: O22– Formula: PO43– Formula: SO42– Formula: SO32– Formula: S2O32–

A GUIDE TO ACIDS, ACID STRENGTH, AND CONCENTRATION
What’s the difference between acid strength and concentration? And how does pH fit in with these? This graphic explains the basics.
HCl H2SO4 HNO3 H3PO4 HF CH3COOH H2CO3
HYDROCHLORIC ACID SULFURIC ACID NITRIC ACID PHOSPHORIC ACID HYDROFLUORIC ACID ETHANOIC ACID CARBONIC ACID
pK a = –7 pK a = –2 pK a = –2 pK a = 2.12 pK a = 3.45 pK a = 4.76 pK a = 6.37
STRONGER ACIDS WEAKER ACIDS
STRONG ACIDS VS. WEAK ACIDS ACIDS, Ka AND pKa CONCENTRATION AND pH
HA H+ + A– The H+ ion is transferred to a

[H+] [A–] pH = –log10[H+] A decrease of one on the pH scale represents
water molecule, forming H3O+
Ka = pKa = –log10[Ka] a tenfold increase in H+ concentration.
A–
[HA] A– A– A–
H+ H+ H H+ H A Ka pKa H+ H+ H+
H+ A H H+ A– H +
A– A
A–
H+ A– H+
A– H
VERY STRONG ACID >0.1 <1 A–
A–
H+ A H A H A H+ H+ H+ H+ A–
+
A – A– H A–
–3
A –
FAIRLY STRONG ACID 10 –0.1 1–3 A–
A– H+ + H A
H A H A A– A– H+ H+ A– A–
H A – H+ H+
–5 –3
WEAK ACID 10 –10 3–5
STRONG ACID WEAK ACID VERY WEAK ACID 10–15–10–5 5–15 CONCENTRATED ACID DILUTE ACID
H+ Hydrogen ions A– Negative ions H A Acid molecules EXTREMELY WEAK ACID <10–15 >15 H+ Hydrogen ions A– Negative ions
Acids react with water when they are added to it, The acid dissociation constant, Ka, is a measure of the Concentration is distinct from strength. It refers to the
forming ions. The degree to which they do this is what strength of an acid. The higher its value, the stronger amount of acid in a given solution. A concentrated acid
determines whether they are strong or weak acids. the acid (i.e. the more readily it ionises in water). pKa contains a large amount of acid in a given volume; a
Strong acids are essentially 100% ionised in solution. converts Ka number to a logarithmic scale that makes it dilute solution contains a small amount. The pH scale
Weak acids ionise very little in solution. easier to compare strengths of different acids. gauges the amount of hydrogen ions in solution.

THE NOBEL PRIZE MEDALS
This year’s Nobel Prizes will soon be awarded. Here we take a look at the composition of the
medals awarded to the winners – as well as a fun bit of chemistry history involving the medals!
PRE-1980 POST-1980
Au APPROX. 96% Au APPROX. 75%
23 CARAT GOLD 18 CARAT GOLD

SOLID GOLD – NO COATING 24 CARAT GOLD COATING
MASS: 200 GRAMS MASS: 175 GRAMS
NOBEL PRIZES & AQUA REGIA DISSOLVING GOLD IN AQUA REGIA
During the Second World War, when Au + 3 HNO3 + 4 HCl HAuCl4 + 3 NO2 + 3 H2O
Germany invaded Denmark, the Nobel
Prizes of physicists Max von Laue AQUA REGIA CHLOROAURIC ACID
and James Franck were dissolved in
aqua regia (a mix of nitric acid and
RECOVERING GOLD FROM AQUA REGIA
hydrochloric acid) by the Hungarian
chemist George de Hevesy. This
prevented them being discovered, and 3 NaHSO3 + 2 HAuCl4 + 3 H2O 3 NaHSO4 + 8 HCl + 2 Au
the gold was later recovered from the
solution and the medals recast. SODIUM BISULFITE ELEMENTAL GOLD

BY NC ND
DEVELOPING ADVANCED LITHIUM ION BATTERIES
ARGE HARG
CH ISC
HOW DO LITHIUM BATTERIES WORK? ELECTRON FLOW ELECTRON FLOW
E
Lithium ion batteries usually use
lithium cobalt oxide (LiCoO2) for the
positive electrode and graphite for Li+ Li+ Li+ Li+ Li+ Li+
+ + +
Li Li Li Li+
the negative electrode. Li+ Li+ Li+ Li+ Li+ Li+
Li+ Li+ Li+ Li+ Li+
When you charge the battery, Li +
Li +
Li +
Li+
lithium ions and electrons move Li +
Li +
Li +
Li +
Li+
from the positive electrode to + Li+ Li+
– + Li+ Li+ –
the negative electrode. When ELECTROLYTE
(lithium salt dissolved in organic liquid)
ELECTROLYTE
the battery is discharging, the
opposite happens and the flow of
electrons powers the device.
CHARGING BATTERY DISCHARGING BATTERY
SIDE REACTIONS
95 A downside to lithium ion
batteries is the amount of time
O O
90 O they take to charge. Also, other
CAPACITY (%)
H3C CH3 chemistry can occur inside the

85 O O O
LiPF6 battery, impacting performance.
80
The electrodes and the electrolyte
75 can take part in “side reactions”,
ELECTROLYTE COMPOUNDS
and can lead to older batteries
70
50 100 150 200 250
not lasting as long as they did
DEGRADATION PRODUCTS when they were new.
CHARGE CYCLES
TITANIUM
TiO2
14 15
Nb2O5
Na+ Na+ Na+
NIOBIUM
Si P
+
Na Na +
Na+ Na+ Na+

Na+ Na+
Na+
Na+ Na+
Na+
Na+
SILICON PHOSPHORUS
MIXTURES TiNb2O7 + Na+ Na+ – –
ALTERNATIVE OXIDES SODIUM ION BATTERIES NEW ANODE MATERIALS
Titanium and niobium oxides take Operate on the same principles as Silicon or phosphorus can be used
in and give out lithium ions much lithium ion batteries, but are much instead of graphite. They store
quicker, which could lead to fast cheaper; however, they require more energy for their size, and
charging or high power capabilities. different electrode materials. could give longer-lasting batteries.
WHY DOES THIS RESEARCH MATTER?

Improving battery technology can provide us with faster-charging,
longer-lasting batteries. It could also lead to new applications as
higher power batteries become possible.
Based on research and materials provided by Kent J Griffith, PhD candidate at the University of Cambridge.
© Andy Brunning 2016 – www.compoundchem.com/chemunicate

CHEMUNICATE Shared under a CC Attribution-NonCommercial-NoDerivatives licence. BY NC ND
THE CHEMISTRY OF
GUNPOWDER CHARCOAL
Consists of broken down cellulose
and provides carbon and other fuel
for the reaction.
SALTPETRE
Saltpetre is a common name for
potassium nitrate. It supplies oxygen
for the combustion reaction.
SULFUR
Sulfur, also referred to as brimstone,
lowers the ignition temperature
Products of Combustion required to start the reaction.
ENERGY DENSITY
56% SOLID
PRODUCTS 43% GASEOUS
PRODUCTS 1% WATER
3 MEGAJOULES PER KG
75% 15% 10%

Potassium Nitrate Charcoal Sulfur
KNO3 C S
A SIMPLIFIED EQUATION FOR THE BURNING OF BLACK POWDER
10KN0 3 + 8C + 3S 2K 2 CO 3 + 3K 2 SO 4 + 6CO 2 + 5N 2
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THE CHEMISTRY OF STAIN REMOVAL
A number of substances can stain clothes or furnishings, and some can be stubborn to remove. A range of chemicals can help do the job, varying
depending on the type of stain. Stains will often have more than one characteristic, meaning a mix of these agents is often used to facilitate their removal.
ENZYMATIC STAINS OXIDISABLE STAINS GREASY STAINS PARTICULATE STAINS

Blood, grass, chocolate Tea, coffee, red wine Oil, collar stains, butter Mud, soil, dirt
ENZYMES BLEACHES SURFACTANTS BUILDERS

O R O R O
H H
H O Na+ O O O
N N O-
N N
H H O O OH SODIUM STEARATE P P P
R O R O -
O-
Anionic surfactant
H O O O O
EXAMPLE PROTEIN MOLECULE SECTION
HYDROGEN PEROXIDE & PERACETIC ACID
N+ Cl- O- O- O-
CH2OH CH2OH CH2OH HEXADECYLTRIMETHYLAMMONIUM CHLORIDE TRIPHOSPHATE (ABOVE)
Cationic surfactant Triphosphates used to be commonly used as builders in
O O O Oxidise coloured substances to colourless detergents. Due to the environmental impact of phosphates,
OH OH OH
O O ones by breaking down chromophores, OH
many modern detergents are now turning to zeolites.
OH OH sections of chemical structures that can O
OH OH n OH
cause colouration. Bleaches are often n Nax[(AlO2)x(SiO2)y.zH2O
POLYETHYLENE ETHOXYLATE
STARCH MOLECULE either oxygen-based or chlorine-based. Nonionic surfactant GENERAL FORMULA OF BUILDER ZEOLITES
Enzyme-based agents help to break down The oxidising agent in oxygen-based Surfactants help oils and grease dissolve Builders are compounds that help soften
proteins, starches and fats by breaking up bleaches is hydrogen peroxide; this is less in water. They are molecules that have hard water by removing calcium and
the large, insoluble molecules into smaller, effective below 40˚C, so the compound a water-soluble ‘head’ and a oil-soluble magnesium ions. This helps remove soil
more soluble ones. Proteases break down tetraacetylethylenediamine (TAED) is ‘tail’. They form spherical structures called molecules, as they are often bound to
proteins, amylases break down starch, and included to produce peracetic acid, a micelles around oil droplets, which then fabrics by calcium ion bridging. They also
lipases break down fats. better oxidising agent. allows them to dissolve in water. enhance the action of surfactants.

C Graphic shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 licence. BY NC ND
THE CHEMISTRY OF SWIMMING POOLS
Chlorination of swimming pools isn’t as simple as you might think – and there’s a lot of chemistry behind it. There’s also a good chemical reason to avoid
urinating in a swimming pool, due to chemical reactions that can occur. Here we take a detailed look at swimming pool chlorination and chemistry.
CHLORINATING AGENTS PEE IN THE POOL & CHLORAMINES
N Cl N Cl N Cl
H H Cl
Cl2 NaClO Ca(ClO)2
H Cl Cl
L TO R: MONOCHLOROAMINE, DICHLOROAMINE, & TRICHLOROAMINE
L TO R: CHLORINE, SODIUM HYPOCHLORITE & CALCIUM HYPOCHLORITE Ammonia and ammonia-like compounds found in human
sweat and urine react with hypochlorous acid, producing
Due to the hazards associated with its storage and use, chloramines. It is these, not chlorine, that cause the
chlorine gas is now rarely used for chlorination of pools. characteristic smell of swimming pools. They can cause
Instead, hypochlorite salts tend to be used. Calcium wheeziness and sore eyes for some swimmers.
chloride is also often added to pool water; this prevents
calcium sulfate, which is a slightly soluble component of
the grouting between tiles in pools, from dissolving.
THE CHEMICAL REACTIONS INVOLVED IN CHLORINATION

POOL SMELL RESPIRATORY EFFECTS SORE EYES
NaClO + H2O Na+ + OH− + HClO

Chlorine and hypochlorite salts both react with water to Peeing in the pool helps produce more trichloroamine,
HYPOCHLOROUS ACID produce the strong oxidant hypochlorous acid. This is as the uric acid present in urine helps to create it. It also
Strong oxidant, chief bactericidal agent produces small amounts of cyanogen chloride. Chlorine
the major bactericidal agent in pool water.
contained in these kinds of by-products of chlorination is
In water, hypochlorous acid exists in equilibrium with referred to as ‘combined chlorine’ (CC).
HOCl + H2O H3O+ + OCl− the weaker oxidant, the hypochlorite ion. The combined
HYPOCHLORITE ION concentration of these chemicals in pool water is
Weak oxidant; formation favoured by higher pH referred to as ‘free available chlorine’ (FAC). O
Hypochlorite ions are rapidly broken up by the UV light
H LEFT: URIC ACID
2OCl + νUV− −
2Cl + O2 N BELOW: CYANOGEN CHLORIDE
present in sunlight, and this causes 90% of the FAC HN
2HOCl + νUV 2HCl + O2 loss from outdoor pools. This means that outdoor pools O
require more frequent chlorination – or the addition of
UV LIGHT PHOTOLYSIS other chemicals to stabilise the FAC levels. O N N N C Cl
Hypochlorite breaks down faster than hypochlorous acid H H

FIREWORK BANGS, CRACKLES & WHISTLES
The colours of fireworks get a lot of attention when it comes to explaining the chemistry behind them. However, there’s also a lot of chemistry
behind the assorted noises that fireworks make. Here, we take a brief look at what causes the bangs, crackles and whistles in fireworks displays.
FIREWORK BANGS WHISTLING FIREWORKS
O
OXIDISER
+ SULFUR
+ METAL O
e.g. KClO3 or antimony usually Al
sulfide HO
OH
O- Na+
These are produced by the ignition of an explosive mixture
of compounds; usually an oxidiser (potassium chlorate or
HO
potassium perchlorate), sulfur, and aluminium. They produce
OH
OH
a flash of light and a loud bang, so are often referred to as
‘flash and sound’ mixtures.
GALLIC ACID SODIUM SALICYLATE
Compacted, confined gunpowder also produces a large bang.
O O2N NO2
CRACKLING FIREWORKS
O- K+ HO
NO2
Pb3O4 Bi2O3 (BiO)2CO3
POTASSIUM BENZOATE PICRIC ACID

L TO R: LEAD TETROXIDE, BISMUTH TRIOXIDE, BISMUTH SUBCARBONATE
Fireworks owe their whistle to aromatic organic compounds

Crackling fireworks were originally made using lead tetroxide such as those shown. These are mixed with oxidisers, (e.g
mixed with magnalium (an aluminium-magnesium alloy). The potassium perchlorate), and tightly packed into a tube.
mixture is divided into small granules; their rapid combustion Small explosions caused by the aromatic compounds lead to
produces the crackling effect. Due to lead’s toxicity, bismuth oscillations in the gases created by the burning mixture. This
compounds are now more commonly used. creates a standing wave in the tube, producing a whistle effect.

4TH FEBRUARY – PATENT ISSUED FOR TEFLON (1941)
F F F F
C C C C
F F F F
n
TETRAFLUOROETHENE POLYTETRAFLUOROETHENE
Teflon is the brand name for polytetrafluoroethene (PTFE). It’s a white, waxy substance,
and was actually created by accident by Roy Plunkett in 1938. During research on new
TEFLON PAN refrigerants, the tetrafluoroethene Plunkett was using was accidentally polymerised.
HOW DOES IT WORK? IS TEFLON SAFE?
F F F F F F F
327˚C MELTING POINT
260˚C
C C C C C C C RECOMMENDED MAX
SAFE USE TEMPERATURE
F F F F F F F
During appropriate use, Teflon does not reach the
temperatures required for it to degrade. However, if the
Teflon’s non-stick properties are in part due to the strength coating is overheated the polymer can begin breaking
of its carbon–fluorine bonds, which are chemically inert. down, and the fumes produced can cause flu-like
Additionally, due to the fluorine atoms, the intermolecular symptoms. At present, the long term effects of human
forces between PTFE and other molecules are very weak. exposure to these fumes are still largely unknown.

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A GUIDE TO COMMON HOUSEHOLD PLASTICS
Plastics are substances called polymers – these are long, chain-like molecules, formed from many smaller molecules. We use a number of
different plastics in our day-to-day lives. This graphic looks at uses of the most frequently encountered, along with their chemical structures.
PE POLYETHENE PP POLYPROPENE PVC POLYVINYLCHLORIDE PET POLYETHYLENE TEREPHTHALATE
H H H CH3 H Cl O O
C C C C C C
O O
n
H H n H H n H H n
Polyethene is the most produced plastic, Polypropene is particularly resistant to PVC comes in both rigid and flexible forms. PET is a lightweight polymer, and comes
and comes in a number of different forms, heat, physical damage, and corrosion. As a In its rigid form, it can be used for window in forms of varying rigidity. It’s commonly
including high density polyethene (HDPE) consequence, it is commonly used in food and door frames, piping, and bank cards. used for plastic drink bottles, and also for
and low density polyethene (LDPE). It is containers, carpets and rugs, ropes, plastic By adding plasticisers, a more flexible form clothing fibres (where it’s often referred to
used in plastic bags, bottles, plastic films, furniture, and piping. It’s also used to make can be obtained, which is used in electric generally as ‘polyester’). Additionally, it’s
piping, and toys. It is not biodegradable. items for medical or laboratory uses. cable insulation, and as a rubber substitute. used in ready meal packing and tapes.
PS POLYSTYRENE PTFE POLYTETRAFLUOROETHENE PA NYLON (POLYAMIDE) PU POLYURETHANE
F F H H
H H H O O
N O O N
C C C C N (CH2)6 N C (CH2)64 C R C R C
n
O O n
H H n F F n
Polystyrene is one of the most widely PTFE’s well-known brand name is Teflon. Nylon actually refers to a family of Polyurethanes are also a family of polymers;
used plastics. It’s used in its solid form It’s a very unreactive polymer, and is used in polymers; nylon 6,6 is shown here. It was the R group in the structure above varies.
to produce plastic cutlery, CD cases, and non-stick coatings on cookware. Gore-tex originally intended as a synthetic silk Their uses include foam seating, for both
disposable razors, whilst as a foam it’s used fabrics also contain PTFE-based fibres. It replacement, for military applications such furniture & cars, non-latex condoms, shoe
in packing materials, building insulation, also has applications as a lubricant, and as as parachutes. Today, it is used in clothing, soles, football coatings, skateboard and
and foam containers for food and drink. insulation for electric wires and cables. guitar strings, and fishing lines. roller-blade wheels, and some varnishes.

C CC Attribution-NonCommercial-NoDerivatives licence. Photo: CC-BY licence, Pump Aid: https://www.flickr.com/photos/worldwaterday/8534578744 BY NC ND
THE COMPOSITION OF OSCAR STATUETTES
The Academy Awards are coming up this weekend, and each of the winners will walk away with an Oscar statuette. Here's what they're made of!
COMPOSITION: PRE-2016 COMPOSITION: 2016–PRESENT
INTERIOR: BRITANNIUM INTERIOR: BRONZE

Al
Sn Sb Cu Cu Sn Ni Mn
Zn
TIN ANTIMONY COPPER COPPER TIN OTHERS
93% 5% 2% 88% 12% TRACE

EXTERIOR: 24-KARAT GOLD EXTERIOR: 24-KARAT GOLD
Before the 2016 awards, the Oscar statuettes Since 2016 the Oscar statuettes have been cast
were made from britannium, an alloy of in bronze (an alloy consisting of copper, tin, and
tin, antimony and copper. This was then often very small amounts of other metals) then
electroplated with copper, nickel, silver, and coated in 24-karat gold. This is a reversion to
finally 24-karat gold. The statuettes were made their original composition; for the initial awards
from plaster for three years during World War ceremonies, after the Oscars were founded in
II due to metal shortages, but winners later 1929, gold-coated bronze statues were awarded
received the usual gold statuettes. before the switch to britannium.

THE CHEMISTRY OF AN ELECTRIC GUITAR
The electric guitar as we know it today owes a lot to the materials that make it up. In this graphic, we take a look at the different magnetic
mixtures used in the electric guitar pickups, the alloys used in the frets and strings, and the chemicals used to give the guitar a glossy finish.
GUITAR PICKUPS GUITAR STRINGS
Al Ni Co Sm Nd Fe Ni Fe C Mn Cr
Guitar pickups are built around permanent magnets. Alnico

magnets (made from aluminium, nickel, and cobalt) are
most commonly used, but ceramic magnets (based on iron
oxide with strontium or barium carbonate), samarium cobalt
magnets and neodymium magnets can all also be used. Electric guitars require their strings to contain a magnetic
metal. Usually, this is in the form of steel. The thicker strings (E,
A & D) are usually wound with nickel wire. For some strings, a
MAGNETS polymer coating is used to help to prevent corrosion.
COILED WIRE
GUITAR FINISH
1 2 3
NO2
Strings vibrate in Flux of magnetic Causes current to NO2
O
magnetic field field in coil changes flow in coil O2N O H H H
O O N N O O N
O O R C R C R
O O
O2N O O O
GUITAR FRETS O2N O
NO2
n
n
Ni Cu Zn Fe C Cr NITROCELLULOSE POLYURETHANE
Some guitars have a nitrocellulose lacquer finish, consisting of

Frets are commonly made from nickel-silver (an alloy of copper, nitrocellulose mixed with other compounds and dissolved in a
nickel, and zinc), but stainless steel can sometimes be used (an solvent. Polyurethane and polyester finishes are also common.
alloy of iron, carbon, and chromium which prevents corrosion). They also tend to be more durable than nitrocellulose lacquer.

THE CHEMISTRY OF DIAMOND RINGS
Diamond rings are synonymous with engagements; diamond itself is an form (allotrope) of carbon, but other chemical elements can impact on
its appearance. Here we look at ‘the 4 Cs’ and their chemistry links, as well as some of the metallic elements that help to make up the ring itself.
DIAMOND CUT DIAMOND CARAT
0.25 Ct 0.50 Ct 0.75 Ct 1.00 Ct 1.50 Ct 2.00 Ct
4.1 mm 5.2 mm 5.8 mm 6.5 mm 7.4 mm 8.2 mm
SHALLOW IDEAL DEEP Top: weight in carats; Bottom: approximate diameter in millimetres.
Diamonds not shown to scale, but are in proportion to each other.
The cut of a diamond affects how well it reflects light. Diamond carat measures mass; one carat is equal to two
Too shallow or too deep and the reflection of light is poor, hundred milligrams. Diameters are approximate, as they
so the diamond seems to sparkle less. vary depending on the cut of the diamond.
DIAMOND COLOUR DIAMOND CLARITY RING COMPOSITION

WHITE GOLD
Au 75% Pd 10% Ni 10% Zn 5% Rh PLATE
D→F G→J K→M N→R S→Z F → IF VVS1/2 VS1/2 SI1/2 I1/2/3

ALMOST FAINT VERY LIGHT LIGHT
COLOURLESS COLOURLESS YELLOW YELLOW YELLOW FLAWLESS OR VERY VERY VERY
SLIGHTLY
STERLING SILVER
INTERNALLY SLIGHTLY SLIGHTLY INCLUDED
INCLUDED
FLAWLESS INCLUDED INCLUDED
Ag 92.5% Cu 7.5% Pt TRACE Ge TRACE Zn TRACE

POTENTIAL ELEMENTAL IMPURITIES GAINED DURING DIAMOND GROWTH
7 5 1 14 15 28 27
YELLOW GOLD
N
NITROGEN
B
Boron
H
HYDROGEN
Si
silicon
P
PHOSPHORUS
Ni
Nickel
Co
cobalt
Compositions given are
TYPE Ia TYPE Ib TYPE IIa TYPE IIb approximate for a typical
0–0.3% N 0–0.05% N 0% N B impurities Au 75% Cu 12.5% Ag 12.5% alloy, and can vary slightly
(clusters) (diffuse)
Most diamonds have some imperfections. These can be
internal or external, and include chips, scratches, carbon
The colour of diamonds is influenced by impurities. Nitrogen spots due to carbon not completely crystallising when the The ring itself can be fashioned from a variety of metals.
impurities can give a yellow hue, whereas boron impurities diamond was formed, or artefacts due to the presence of Alloys of gold and silver are common, but platinum rings and
give much rarer blue diamonds. Type Ia are most common. other impurities in the diamond. palladium rings are also popular, and more durable.

THE CHEMISTRY OF SILLY PUTTY
Silly putty is an odd substance – it can be slowly stretched out, but snaps if pulled apart with greater force. It can be molded into shape,
but bounces if rolled into a ball. What’s behind these strange properties? Here’s a quick look at the chemical composition and explanation.
WHAT IS IT MADE OF? HOW DOES IT WORK?
The most important compound in silly putty The presence of PDMS alone, and its
is polydimethylsiloxane (PDMS). This is the viscoelasticity, doesn’t fully explain how silly
simplest member of the polymer family known putty behaves. Another ingredient, boric acid,
as the silicones. also makes a telling contribution.
PDMS is viscoelastic. This means that it acts
The boric acid helps to create ‘crosslinks’
like a viscous liquid and flows over long time
between adjacent polymer chains. These help
scales. However, over short time scales (for
to give silly putty its putty-like nature, and also
example, being rolled into a ball and thrown at
help explain its strange behaviour.
a hard surface), its behaviour is elastic, and it
will bounce back.
R Si O O Si R
–
EXAMPLE BORON-MEDIATED CROSSLINK
(R represents the rest of the PDMS polymer chain)
B
Si Si Si
O O
R Si O O Si R
n
A POLYDIMETHYLSILOXANE The polydimethylsiloxanes in silly putty end in Si-OH groups. The boric
(solid filled atoms represent carbon; smaller outlined atoms represent hydrogen) acid reversibly reacts with these to form short-lived crosslinks between
polymer chains. Slow deformation gives these crosslinks time to break
and reform, allowing viscous flow, but rapid, forceful deformation does
At high molecular weights, the flexible polymer chains become loosely
not, so elastic behaviour is instead seen.
entangled, which contributes to PDMS’s viscoelasticity.

THE CHEMISTRY OF A FOOTBALL SHIRT
POLYESTER ELASTANE
Polyesters are a group of polymers commonly Also known as spandex or lycra, elastane is
used in textile applications. The polymer is another polymer often incorporated into
a very large molecule built up from smaller football shirts. It can resist approximately
molecules. The basic synthesis of polyesters 600% elongation before rupturing, so it is
involves a condensation reaction between useful for adding strength and elasticity to
an alcohol and a carboxylic acid; there are football shirts. However, it is not as ‘breathable’
several methods through which this can be as other materials.
accomplished.
O O
H
AIA
N
O O O N
H
N
H
N
H
a b
ELASTANE
O O
n
POLYETHYLENE TEREPHTHALATE (PET)
Most common type of polyester used in textiles.
Occasionally combined with cotton (below) to form polycotton
POLYURETHANE
The name, number, and sponsor logo on the
OH shirt are often made of polyurethane, though
OH
HO O materials can vary. These can be thermally
O O
O HO bonded to the shirt using a heat-press.
OH OH
n
COTTON
H H H
N N O O N
Polyester is durable, lightweight, resistant to R C R C R
creasing, and only absorbs 0.4% of its weight O O
of water. For this reason, it has a good ‘wicking’ n
effect - most sweat is carried along the fibres, POLYURETHANE
rather than absorbed, and can evaporate.

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BY NC ND
THE CHEMISTRY OF A FOOTBALL SHIRT
POLYESTER
SHIRT MATERIAL – POLYESTER SHIRT MATERIAL – ELASTANE ELASTANE
Polyesters are a group of polymers Also known as spandex or lycra, elastane
commonly used in textile applications. The is another polymer often incorporated into
polymer is a very large molecule built up football shirts. It can resist approximately
from smaller molecules. The basic synthesis 600% elongation before rupturing, so it is
of polyesters involves a condensation useful for adding strength and elasticity
reaction between an alcohol and a to football shirts. However, it is not as
carboxylic acid; there are several methods ‘breathable’ as other materials.
through which this can be accomplished.
O O
H
N
O O O N
H
N
H
N
H
a b
ELASTANE
O O
n
POLYETHYLENE TEREPHTHALATE (PET)
NAME & NUMBER – POLYURETHANE POLYURETHANE
OH The name, number, and sponsor logo on the
OH
O shirt are often made of polyurethane. These
HO
O O are thermally bonded to the shirt using a
O HO
OH heat-press.
OH
n
COTTON
H H H
Polyester is durable, lightweight, resistant to N N O O N
creasing, and only absorbs 0.4% of its weight R C R C R
of water. It has a good ‘wicking’ effect - most O O
sweat is carried along the fibres, rather than n
absorbed, and can evaporate. POLYURETHANE

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence.
BY NC ND
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GRAPHENE: THE CARBON-BASED ‘WONDER MATERIAL’
Since its discovery in 2003, graphene has been a hot topic in chemistry and materials science research. It’s been linked with water purification, electronics,
and biomedical applications. However, how close are we really to using graphene in our day-to-day lives? This graphic looks at its properties, uses, and future.
WHAT IS GRAPHENE? POTENTIAL USES OF GRAPHENE

SINGLE LAYER OF CARBON ATOMS
TOUCH SCREENS IN DEVICES
HONEYCOMB-LIKE STRUCTURE
Graphene’s transparency and conductivity means that
GRAPHITE IS LAYERS OF GRAPHENE
it can be used in displays and touchscreens. However,
currently these are more expensive to produce than
ISOLATED IN 2003 IN MANCHESTER the currently used material, indium tin oxide.
Graphene is a single layer of graphite, the carbon-based WATER FILTRATION SYSTEMS

material found in pencil leads. Graphite has been known
for centuries, but graphene was only isolated in 2003, by Graphene allows water to pass through it, but not
other liquids and gases, so it can be used in water
shearing layers off of graphite using sellotape. It’s a single
purification. Researchers are working on a device that
atom-thick layer of carbon atoms, that are arranged in a
could be capable of filtering salt from sea water.
flat, hexagonal lattice structure.
IN ELECTRONIC DEVICES
THE PROPERTIES OF GRAPHENE Graphene has been touted as silicon’s successor, and
has been used to make very fast transistors. However,
its conductivity cannot be ‘switched off’ as silicon’s
can. Other 2D materials seem more promising.
MEDICAL SENSORS & DRUG DELIVERY

Several biomedical applications are being explored
for graphene, including drug delivery, cancer therapy,
and its use as a sensor. However, its toxicity profile
HIGH ELECTRICAL 200x STRONGER THIN AND HIGH THERMAL VERY HIGH must be investigated before any clinical uses.
CONDUCTIVITY THAN STEEL LIGHTWEIGHT CONDUCTIVITY TRANSPARENCY
ENERGY STORAGE & COMPOSITES
Graphene’s ‘wonder material’ reputation stems from its superlative properties. It is a million times thinner
Graphene-based energy storage devices are possible.
than a piece of paper, yet stronger than diamond, and 200 times stronger than steel, due to the strong It can also substitute for graphite in normal batteries,
carbon-carbon bonds. It’s also a flexible material, and conducts heat and electricity better than copper. improving efficiency. Additionally, it can be added to
Being only one atom thick, almost 98% of visible light passes through graphene, making it transparent. materials to make them stronger and more lightweight.

COMPOSITIONS OF UK COINS
OUTER RING INNER CIRCLE
COPPER 76%
75% COPPER
ZINC 20%
25% NICKEL
NICKEL 4%
PRE-2017 POST-2017
In 2014, the Royal Mint announced a
COPPER 70% new £1 coin specification, proposed
to enter circulation in 2017 to combat
counterfeiting. 3% of all current £1
ZINC 24.5% coins are estimated to be counterfeit.
The new £1 will be bi-metal and twelve-
sided. The precise metal composition
NICKEL 5.5% is yet to be determined.
CURRENT COMPOSITION CHANGE IN SIZE

After a review of coinage in 1994, the
COPPER 75% UK government decided a smaller
50p was required. This coin was then
introduced in 1997. The diameter
was reduced from 30mm to 27.3mm;
NICKEL 25% however, the metal composition of
the coin remained identical.
CURRENT COMPOSITION
The 20p has not undergone any
changes in composition or size since it
COPPER 84% first entered circulation in 1982. Due
to a minting error in 2008, around
250,000 coins were produced without
NICKEL 16% a date. These coins remain legal
tender.
PRE-2011 POST-2011
Change to nickel-plated steel
COPPER 75% MILD STEEL
94% IRON, CARBON & MANGANESE
NICKEL 25% 6% NICKEL
PRE-1992 POST-1992
Change to copper-plated steel
COPPER 97%
94% MILD STEEL
IRON, CARBON & MANGANESE
ZINC 2.5%
6% COPPER
TIN 0.5%

BY NC ND
THE NOBEL PRIZE MEDALS
This year’s Nobel Prizes will soon be awarded. Here we take a look at the composition of the
medals awarded to the winners – as well as a fun bit of chemistry history involving the medals!
PRE-1980 POST-1980
Au APPROX. 96% Au APPROX. 75%
23 CARAT GOLD 18 CARAT GOLD

SOLID GOLD – NO COATING 24 CARAT GOLD COATING
MASS: 200 GRAMS MASS: 175 GRAMS
NOBEL PRIZES & AQUA REGIA DISSOLVING GOLD IN AQUA REGIA
During the Second World War, when Au + 3 HNO3 + 4 HCl HAuCl4 + 3 NO2 + 3 H2O
Germany invaded Denmark, the Nobel
Prizes of physicists Max von Laue AQUA REGIA CHLOROAURIC ACID
and James Franck were dissolved in
aqua regia (a mix of nitric acid and
RECOVERING GOLD FROM AQUA REGIA
hydrochloric acid) by the Hungarian
chemist George de Hevesy. This
prevented them being discovered, and 3 NaHSO3 + 2 HAuCl4 + 3 H2O 3 NaHSO4 + 8 HCl + 2 Au
the gold was later recovered from the
solution and the medals recast. SODIUM BISULFITE ELEMENTAL GOLD

BY NC ND
DEVELOPING CHEAPER LAB-ON-A-CHIP DEVICES WITH 3D PRINTING
WHAT IS A LAB-ON-A-CHIP?
C C C C
A lab-on-a-chip (LOC) is a small
C C
handheld device that is able to
Si Si Si
carry out tasks that usually require
O O
a laboratory. Everyday examples C
C n
include diabetic blood glucose tests
and home pregnancy tests.
10.4
POLYDIMETHYLSILOXANE
However, current LOC design is time-
consuming and restrictive. Most are
made by forming individual layers OK
of polydimethylsiloxane (PDMS) and pregnant
not pregnant
bonding them together.
An alternative to current LOC

LASER
design is using 3D printing.
Stereolithography can be used;
this uses a resin bath, which
contains molecular building blocks
(monomers) and photointiators
which release cations or radicals
CURED POLYMER when exposed to light.
A laser provides the light needed,
MOVEABLE PLATFORM and the cations or free radicals
react with the monomers, forming
RESIN a large, solid polymer network. This
is called photopolymerisation.
HOW DOES THE PHOTOPOLYMERISATION PROCESS WORK?
·
LASER MONOMER
PHOTOINITIATOR RADICAL/ION POLYMER

3D printed lab-on-a-chip devices are much quicker and cheaper to
$12
PER
ONLY TAKE A FEW
HOURS TO PRINT
produce. They can be used for a range of purposes, including disease
diagnosis in epidemic-hit areas, or as particle analyser chips. CHIP
Based on research and materials provided by Sarah Hampson, PhD candidate at Loughborough University, UK.

RECYCLING RATES OF SMARTPHONE METALS
COLOUR KEY: < 1% RECYCLE RATE 1–10% RECYCLE RATE 10–25% RECYCLE RATE 25–50% RECYCLE RATE > 50% RECYCLE RATE NON-METAL (OR RECYCLE RATE UNKNOWN)
SCREEN ELECTRONICS
49
49
TOUCH: INDIUM TIN OXIDE WIRING & MICROELECTRONICS 29 47
In
Indium 8 Used in a transparent film over Copper is used for wiring, and for Cu
COPPER
Ag
Indium 8 SILVER
O the phone’s screen that conducts micro-electrical components along

50
OXYGEN
Oxygen
electricity. This allows the screen to with gold and silver. Tantalum is 79 73
function as a touch screen. This is the major component in micro-
Sn TIN the major use of indium. capacitors.
AuGOLD
Ta
TANTALUM
66
13 14
GLASS: ALUMINA & SILICA MICROPHONES & VIBRATIONS 28 59
Al
Aluminium
Si
SILICON On most phones the glass is Nickel is used in the microphone Ni
NICKEL
Dy Pr
PRASEODYMIUM
DYSPROSIUM
aluminosilicate glass, a mix of and for electrical connections.
aluminium oxide & silicon dioxide. Rare earth element alloys are used
It also contains potassium ions
8 19 65 60 64
in magnets in the speaker and
O
OXYGEN
K
POTASSIUM which help strengthen it. microphone, and the vibration unit. Tb
TERBIUM
Nd
NEODYMIUM
Gd GADOLINIUM
39 57 65
COLOURS: RARE EARTH METALS THE SILICON CHIP 14 8 51
Y La Tb Pure silicon is used to manufacture Si O Sb

Yttrium LANTHANUM TERBIUM A variety of rare earth metal- SILICON OXYGEN ANTIMONY
containing compounds are used the chip, which is then oxidised to

to help to produce the colours in produce non-conducting regions.
Other elements are added to allow
33 15 31
59 65 66
Pr Eu Dy a smartphone’s screen. Some of

the chip to conduct electricity.
As P Ga
PRASEODYMIUM Europium DYSPROSIUM these compounds are also used ARSENIC PHOSPHORUS GALLIUM
to help reduce light penetration

64
into the phone. Many of the ‘rare
Gd earths’ occur commonly in the CONNECTING ELECTRONICS 50 82
GADOLINIUM Earth’s crust, but often at levels too Tin & lead were used in older Sn Pb
low to be economically extracted. solders; newer, lead-free solders
TIN LEAD
use a mix of tin, copper & silver.
BATTERY CASING
Magnesium alloy is used to make some phone
3 27
Most phones use lithium ion batteries, composed
6 12
Li
LITHIUM
CoCOBALT of lithium cobalt oxide as a positive electrode cases, whilst many others are made of plastics, C Mg
8 CARBON
which are carbon-based. Plastics will also include
MAGNESIUM
O and graphite (carbon) as the negative electrode.

6 13
OXYGEN
Sometimes other metals, such as manganese, are flame retardant compounds, some of which contain
used in place of cobalt. The battery casing is often bromine, whilst nickel can be included to reduce
35 28
C Al electromagnetic interference. Br Ni
CARBON ALUMINIUM
made of aluminium. BROMINE NICKEL

OLYMPIC MEDAL COMPOSITIONS
What are the medals given out at the Rio Olympics made of? It’s not quite as simple as you might think...
1 2 3
GOLD MEDAL SILVER MEDAL BRONZE MEDAL
Ag SILVER
PURITY: 92.5%
98.8% Ag SILVER
PURITY: 92.5%
100% Cu COPPER
PURITY: 93.7%
95%
Au GOLD
PURITY: 99.9%
1.2% The silver purity of 92.5% is Zn ZINC
PURITY UNDISCLOSED
5%
a minimum IOC requirement.
Around 30% of the silver used
to make the medals for the Rio
The gold used in the gold medals Olympics was obtained from Some copper used in the bronze
for the Rio Olympics is entirely recycled sources, including car medals came from recycled
free of mercury impurities. parts, X-ray plates, and mirrors. materials at the Brazilian Mint.
The compositions given in this graphic are according to the Brazilian Mint. All percentages are by weight.

BY NC ND
DEVELOPING ADVANCED LITHIUM ION BATTERIES
ARGE HARG
CH ISC
HOW DO LITHIUM BATTERIES WORK? ELECTRON FLOW ELECTRON FLOW
E
Lithium ion batteries usually use
lithium cobalt oxide (LiCoO2) for the
positive electrode and graphite for Li+ Li+ Li+ Li+ Li+ Li+
+ + +
Li Li Li Li+
the negative electrode. Li+ Li+ Li+ Li+ Li+ Li+
Li+ Li+ Li+ Li+ Li+
When you charge the battery, Li +
Li +
Li +
Li+
lithium ions and electrons move Li +
Li +
Li +
Li +
Li+
from the positive electrode to + Li+ Li+
– + Li+ Li+ –
the negative electrode. When ELECTROLYTE
ELECTROLYTE
the battery is discharging, the
opposite happens and the flow of
electrons powers the device.
CHARGING BATTERY DISCHARGING BATTERY
SIDE REACTIONS
95 A downside to lithium ion
batteries is the amount of time
O O
90 O they take to charge. Also, other
CAPACITY (%)
H3C CH3 chemistry can occur inside the

85 O O O
LiPF6 battery, impacting performance.
80
The electrodes and the electrolyte
75 can take part in “side reactions”,
ELECTROLYTE COMPOUNDS
and can lead to older batteries
70
50 100 150 200 250
not lasting as long as they did
DEGRADATION PRODUCTS when they were new.
CHARGE CYCLES
TITANIUM
TiO2
14 15
Nb2O5
Na+ Na+ Na+
NIOBIUM
Si P
+
Na Na +
Na+ Na+ Na+

Na+ Na+
Na+
Na+ Na+
Na+
Na+
SILICON PHOSPHORUS
MIXTURES TiNb2O7 + Na+ Na+ – –
ALTERNATIVE OXIDES SODIUM ION BATTERIES NEW ANODE MATERIALS
Titanium and niobium oxides take Operate on the same principles as Silicon or phosphorus can be used
in and give out lithium ions much lithium ion batteries, but are much instead of graphite. They store
quicker, which could lead to fast cheaper; however, they require more energy for their size, and
charging or high power capabilities. different electrode materials. could give longer-lasting batteries.

Improving battery technology can provide us with faster-charging,
longer-lasting batteries. It could also lead to new applications as
higher power batteries become possible.
Based on research and materials provided by Kent J Griffith, PhD candidate at the University of Cambridge.

THE CHEMISTRY OF SUPERGLUE
Superglue is vital for quick repair jobs, but was actually discovered by accident – twice! It owes its strong adhesive nature to the
particular chemicals it’s composed of. In this graphic, we take a look at them, and how they react to keep things solidly stuck together.
THE HISTORY OF SUPERGLUE HOW SUPERGLUE WORKS
1942 1951 1958 C N

+
C N
H2O H2C C H2O CH2 C –
C O C O
RO RO
Cyanoacrylates discovered during Their potential finally
WWII search for gun sight plastics. realised, the cyanoacrylates
Stick to everything, so discarded. are developed into a glue
Cyanoacrylates ‘cure’ in the presence of water. Only
which eventually becomes a small amount of water is required to kick off the
Cyanoacrylates are rediscovered available commercially in reaction – even the water vapour in the air is enough.
during research looking for 1958. Numerous other
polymers for jet canopies. manufacturers follow suit.
C N C N
+
H2O CH2 C – H2C C
THE CYANOACRYLATES
C O C O
O O RO RO
N N
The reaction produces an anion which can add to
O O more of the original cyanoacrylate, a process that
repeats to form the adhesive polymer chains.
METHYL CYANOACRYLATE ETHYL CYANOACRYLATE N N N N N

The most commonly used cyanoacrylate in superglue
today is ethyl cyanoacrylate, but others, such as
methyl cyanoacrylate, can also be used. Medical n
grade cyanoacrylates such as 2-octyl cyanoacrylate
can be used to close up wounds. COOR COOR COOR COOR COOR
EXAMPLE SECTION OF THE CYANOACRYLATE POLYMER STRUCTURE

ELEMENTS OF A SMARTPHONE
ELEMENTS COLOUR KEY: ALKALI METAL ALKALINE EARTH METAL TRANSITION METAL GROUP 13 GROUP 14 GROUP 15 GROUP 16 HALOGEN LANTHANIDE
SCREEN ELECTRONICS
49 29 47
Indium tin oxide is a mixture of Copper is used for wiring in the
In 8 indium oxide and tin oxide, used phone, whilst copper, gold and silver Cu Ag
Indium Copper Silver
in a transparent film in the screen are the major metals from which
50
O that conducts electricity. This allows microelectrical components are 79 73
Oxygen
the screen to function as a touch fashioned. Tantalum is the major
Sn screen. component of micro-capacitors.
Au Ta
Tin Gold Tantalum
13 14 28 66 59
The glass used on the majority of Nickel is used in the microphone as well
Al Si smartphones is an aluminosilicate as for other electrical connections. Alloys Ni Dy Pr
Aluminium Silicon including the elements praseodymium, Nickel Dysprosium Praseodymium
glass, composed of a mix of alumina
gadolinium and neodymium are used
8 19 (Al2O3) and silica (SiO2). This glass in the magnets in the speaker and 65 60 64
also contains potassium ions, which
O K help to strengthen it.
microphone. Neodymium, terbium and Tb Nd Gd
Oxygen Potassium dysprosium are used in the vibration unit. Terbium Neodymium Gadolinium
39 57 65 14 8 51
A variety of Rare Earth Element Pure silicon is used to manufacture
Y La Tb compounds are used in small the chip in the phone. It is oxidised
Si O Sb
Silicon Oxygen Antimony
Yttrium Lanthanum Terbium
quantities to produce the colours to produce non-conducting regions,
59 63 66 in the smartphone’s screen. Some then other elements are added in 33 15 31
compounds are also used to reduce order to allow the chip to conduct As P Ga
Pr Eu Dy UV light penetration into the phone. electricity. Arsenic Phosphorus Gallium
Praseodymium Europium Dysprosium
64
Tin & lead are used to solder 50 82
Gd electronics in the phone. Newer lead- Sn Pb
Gadolinium
free solders use a mix of tin, copper Tin Lead
and silver.
BATTERY CASING
3 27
6 12
The majority of phones use lithium ion batteries, Magnesium compounds are alloyed to make
Li Co 8 which are composed of lithium cobalt oxide as a some phone cases, whilst many are made C Mg
Lithium Cobalt
O positive electrode and graphite (carbon) as the of plastics. Plastics will also include flame Carbon Magnesium
6 13 Oxygen negative electrode. Some batteries use other retardant compounds, some of which contain 35 28
C Al metals, such as manganese, in place of cobalt. bromine, whilst nickel can be included to
Carbon Aluminium The battery’s casing is made of aluminium. reduce electromagnetic interference.
Br Ni
Bromine Nickel

Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence.
BY NC ND
THE CHEMISTRY OF BIODEGRADABLE PLASTICS
COMMON BIOPOLYMERS & SOURCES EVERYDAY USES OF BIOPOLYMERS ADVANTAGES AND DISADVANTAGES
POLYLACTIC ACID (PLA) GLOBAL PLASTIC PRODUCTION

CONVENTIONAL BIODEGRADABLE &
Biodegradable coffee cups are PLASTICS BIOPLASTICS
O paper cups with a PLA lining to

make the paper waterproof.
333 2.11
million tonnes million tonnes
O n
Use of bioplastics is increasing, but they still account for

Obtained from fermented plant starch from corn, less than 1% of the global plastics market (as of 2018).
cassava, sugar cane or sugar beet.
PLA has the second largest
production volume of any
CONDITIONS FOR BIODEGRADING
POLYHYDROXYALKANOATES (PHAs) biopolymer (behind TPS). It
is also used in plastic films,
CH3 O bottles, and food containers.
O2
H
O OH MOISTURE OXYGEN MICROORGANISMS pH TEMPERATURE
n poly-(R)-3-hydroxybutyrate (P3HB)
Compostable plastics need specific conditions to break

Extracted from bacteria, which produce it via the PLA and TPS both find use down – and take much longer to do so completely if they
fermentation of sugar or lipids. in the manufacture of plastic go to landfill instead of being recycled. However, they still
cutlery that’s biodegradable. break down faster than conventional plastics.
THERMOPLASTIC STARCHES (TPS)

CH2OH CH2OH CH2OH
CO 2
OH
O
OH
O
OH
O CH4
TPS is also used in food waste
O O OH
OH bags and some magazine
OH OH 300–600
OH
wrappers. PHAs have fewer Biodegradable plastics are more expensive than plastics
uses, but have medical uses derived from fossil fuels on weight basis, and require
Starches from plant materials are heated with water, such as in surgical sutures. land to grow raw materials. However, the greenhouse gas
then mixed with plasticisers or other polymers. emissions associated with their production are lower.

THE CHEMISTRY OF CONDOMS
WHAT ARE CONDOMS MADE FROM? LUBRICANTS & OTHER COMPOUNDS
Male condoms are commonly made from Lubricants are usually silicone-based or
latex. To avoid latex allergies, polyurethane water-based. Oil-based lubricants should
condoms can be used instead; polyisoprene not be used with latex condoms as they can
condoms are also available. Female condoms drastically reduce their strength.
are made from polyurethane or nitrile rubber.
1855 1920 Si Si Si
A milky fluid mixture O O
obtained from plants
n
which contains rubber.
n
SPERMICIDES POLYDIMETHYLSILOXANE (PDMS)
a common type of silicone in lubricants
RUBBER RUBBER
POLYISOPRENE
LATEX
Some lubricants used on the inside of

1994 2008 8
condoms contain small amounts of the
H H H OH anaesthetic, benzocaine. It has a numbing
N
R
N O
R
O N
R
O 9
effect that prevents premature ejaculation.
O O n n
O
NONOXYNOL-9
POLYURETHANE POLYISOPRENE
POLYISOPRENE
BENZOCAINE O
(synthetic rubber) Many condoms were often coated with
lubricants containing nonoxynol-9, a NH2
Condoms protect against both pregnancy spermicide. In 2001 the World Health
and sexually transmitted diseases. Studies Organisation concluded there was no Another condom brand has an ‘erectogenic’
show that polyurethane condoms are slightly evidence that this coating gave additional gel (based on nitroglycerin) in the tip. The gel
more prone to breakage than latex ones. protection against pregnancy or STDs. increases blood flow into the penis.

THE CHEMISTRY OF CONTACT LENSES
Simple though they may seem, there’s some complex chemistry behind the contact lenses that many of us use on a daily basis. Here
we take a look at some of the different chemicals that have been used over the years, and how contact lenses have gradually evolved.
RIGID CONTACT LENSES

O2 O2
O2 O2 O2 O2
O2 O2 O2 O2
H3CO O
n
PMMA HARD LENSES RIGID GAS PERMEABLE

first rigid polymer lens impermeable to oxygen permeable to oxygen
Rigid contact lenses, made from poly(methyl methacrylate) (PMMA),

were the first available. Prior to this, glass lenses had to be used.
PMMA lenses weren’t very oxygen-permeable, so improved rigid
materials which were were developed. These more modern rigid
lenses contain silicone and/or fluorine-containing compounds.
CONTACT LENS SOLUTION SOFT CONTACT LENSES

O O CH3 CH3 CH3
H NH NH OH
H3C Si O Si O Si CH3 N O
O O N N N CH3 CH3 CH3
H H H
H n
n n n
PHEMA POLYDIMETHYLSILOXANE (PDMS) POLYVINYLPYRROLIDONE

first soft polymer lens used in elastic soft lenses common hydrophilic co-polymer
HYDROGEN PEROXIDE POLYHEXAMETHYLENE BIGUANIDE
peroxide solutions multipurpose solutions
Soft contact lenses are the most commonly used. These are based
Cleaning solutions are either peroxide or multi-purpose solutions. on hydyrogels, the first of which was poly(hydroxyethyl methacrylate)
Peroxide solution uses peroxide to disinfect; multi-purpose solutions (PHEMA). Hydrogels are networks of cross-linked polymer chains
use polymeric cleaning agents such as biguanides or polyquaterniums. that are highly water-absorbent. More recently, siloxane-containing
Both contain other cleaner & moisturising chemicals. hydrogels which are more oxygen-permeable have been developed.

THE CHEMISTRY OF FOOTBALL SHIRTS
SHIRT MATERIAL: POLYESTER SHIRT MATERIAL: ELASTANE
Polyesters are commonly used in textile Also known as spandex or lycra, elastane
applications. They are polymers, very large is another polymer often incorporated
molecules built up from smaller molecules. into football shirts. It resists approximately
The synthesis of polyesters involves a 600% elongation before rupturing, adding
condensation reaction between an alcohol strength and elasticity to shirts. However, it
and a carboxylic acid. is not as ‘breathable’ as other materials.
O O
H H H
O O O
O N N N
N N N O
H H H
O O
x n
O O ELASTANE
n
POLYETHLYENE TEREPHTHALATE (PET)
SPONSORS, NAMES & NUMBERS
The name, number, and sponsor logo on the
OH shirt are often made of polyurethane. These
OH
HO O are thermally bonded to the shirt.
O O
O HO
OH OH
n
H H H
Polyester is durable, lightweight, resistant N N O O N
to creasing, and only absorbs 0.4% of its R C R C R
weight of water. It has a good ‘wicking’
effect - sweat is carried along the fibres, O O
rather than absorbed, and can evaporate. n
POLYURETHANE

THE CHEMISTRY OF IRONING
What makes your clothes come out of the wash looking all creased? Here’s a look at the chemical reasons, and some chemical solutions!
CREASES, CELLULOSE, & IRONING ANTI-CREASE FABRICS
Plant-based fabrics are predominantly made of the Chemists have come up with ways of producing
natural polymer cellulose. The cellulose chains in the fabrics that avoid post-wash creasing problems. In the
fabric have a network of hydrogen bonds between past urea-formaldehyde resins were added to fabrics
them that helps to hold them all together. to form cross-links between polymer chains, holding
them in place and preventing creasing.
H H
O HO OH O HO OH
O O HO OH
R O O O R HO
O O O
HO OH O HO OH O R O R
H H O
H H HO OH O
O HO OH O HO OH
O O
R O O O R OH
O O N
HO OH O HO OH O
H H O DMDHEU
H H N OH
O HO OH O HO OH
O O
R O O O R
O O O HO OH
HO OH O HO OH O
H H O
R O R
O
CELLULOSE (DASHED LINES SHOW HYDROGEN BOND NETWORK)
HO OH HO
When you wash clothes water breaks up the hydrogen In many of today’s garments, a cross-linker called
bond network, and cellulose chains slide over each dimethylol dihydroxyethylene urea (DMDHEU) is
other. When the clothes dry the hydrogen bond used. This forms covalent bonds between cellulose
network reforms, holding the fabric in its wrinkled chains that lock them in place, preventing creasing.
state. The heat, moisture, and pressure of an iron However, as it can break down over time and release
breaks up this network and forces the cellulose chains low levels of formaldehyde, chemists are still looking
to lie straight, flattening the fabric. at developing better formaldehyde-free cross-linkers.
C © Andy Brunning/Compound Interest 2017 – www.compoundchem.com. Produced in collaboration with Prof Mark Lorch, University of Hull.
WHAT ARE LEGO BRICKS MADE OF?
LEGO BRICKS HOW LEGO IS MADE OTHER LEGO PARTS
Up until 1963, cellulose acetate was used

to make Lego bricks and parts. Lego
bricks are now made from acrylonitrile ABS GRANULES ADDED
butadiene styrene (ABS). ABS is less ABS is opaque, so a polycarbonate

subject to warping and colour fading. polymer has to be used for transparent
Macrolex dyes are added Lego parts. For leaves, bushes and
to ABS to colour it. trees, Lego has recently started using
polyethene derived from sugar cane.
N GRANULES HEATED TO 230˚C (450˚F)
H H
y
C C
H H n x z
MELTED PLASTIC FED INTO MOLDS POLYETHENE SBS

y
N In 2014 more than 60 billion Tyres and elastic materials are made
x Lego pieces were made. from styrene butadiene styrene (SBS).
ABS
z

THE CHEMISTRY OF MATCHES
How Matches Work The Match The Match Box
The composition of matches varies depending POTASSIUM CHLORATE The striking surface of safety match boxes
on type, but safety matches are the most KClO3 Main ingredient (45-55%) in heads of contains red phosphorus and an abrasive
commonly used. They contain a strong safety matches. substance. When struck, a small amount of
oxidising agent in the match head, and red white phosphorus is produced, which ignites.
phosphorus in the striking surface. Striking the S
P
S
PHOSPHORUS SESQUISULFIDE
match causes small amounts of the oxidiser S Component in the heads of ‘strike P P P
P P
and phosphorus to combine, and the heat P anywhere’ matches.
generated by the friction of the striking causes P P P P P P
ANTIMONY (III) SULFIDE P P P
them to ignite. Sb2S3 Added to some matches to make
them burn more vigourously. Red Phosphorus (above); White Phosphorus (below)
Prior to the 1900s, white phosphorus was the
active ingredient in most matches, but this Additionally, the matches contain ammonium P P P P
could cause ‘phossy jaw’ and bone disorders, phosphates to prevent ‘afterglow’, glue to bind P P P P P P P P
and was also toxic, so was replaced. materials, and paraffin wax for ease of burning. P P P P
© COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM | TWITTER: @COMPOUNDCHEM | FACEBOOK: facebook.com/compoundchem

BY NC ND
THE CHEMISTRY OF PAPER AND POLYMER BANKNOTES
The UK recently began its introduction of polymer bank notes. Here we look at the chemistry used in bank notes and their security features.
THE SUBSTRATES SECURITY MEASURES

IN
CI
DE ED
NT E CT
OH FL
RE
OH
HO O GOLD FOIL
O HO O Al
O TRANSMITTED
OH
OH n
12,000 LINES PER CENTIMETRE
CELLULOSE OVDs (Optically Variable Devices) are parts of

the note that change their appearance when
something external to the note changes, such as
Most paper banknotes are actually not made the angle it’s being viewed at. Thin films of gold
from paper, but from around 80% cotton paper. appear green in transmitted light, but gold in
Cotton is made up of the natural polymer reflected light. Thin patterned lines coated with
cellulose – so in a way, paper banknotes are POLYMER BENEFITS aluminium can also provide various colours.
actually polymer banknotes too!
ULTRAVIOLET LIGHT
Harder to counterfeit than
€ €
H CH3
SECURE paper banknotes – more
security features.
POLYPROPYLENE EXCITED STATE EXCITED STATE
ELECTRONS
EXCITED STATE
BACK TO
C C Transparent material, but Waterproof and do not

ELECTRONS
EXCITED
GROUND
STATE
H H
later made opaque with
white ink.
CLEANER get dirty easily, unlike
paper banknotes.
UV
EXCESS
ENERGY
VI
SI
BL
E
n EMITTED
AS LIGHT
GROUND STATE GROUND STATE GROUND STATE
Estimated to last 2.5
Newer polymer notes are usually made from
biaxially oriented polypropylene (BOPP).
DURABLE times longer on average
than paper banknotes. Anti-counterfeiting compounds that fluoresce
‘Biaxially oriented’ refers to the manner in which when placed under ultraviolet light are
it is stretched during production, increasing its also a common security device. Euro notes
Unlike paper banknotes,
use compounds of lanthanide elements to
strength and transparency. White pigment, inks,
and varnish are later applied to the notes.
GREENER polymer notes can be
recycled after use. accomplish this, including those of Europium.

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence.
Image: © Bank of England 2015 (https://www.flickr.com/photos/bankofengland/26830091813) Creative Commons BY-NC-ND Licence BY NC ND
THE CHEMISTRY OF THE WORLD CUP BALL
POLYURETHANE COVERING NYLON LINING
The surface covering of a football is composed Several layers of lining are used between
of synthetic leather; in professional footballs, the covering of the football and the bladder
this is made from polyurethane polymers. The to improve the bounce and strength of the
World Cup ball is made from six polyurethane ball. This lining is made of nylon, another
panels, which are thermally bonded together. class of polymers also known as polyamides.
This covering protects the ball and minimises Polyesters can also be used for this purpose.
water absorption. In cheaper footballs, the
coating can be made from PVC. O
H
N
N
H
N N
O O O n
C R C
H R H
O O
NYLON 6-6
ISOCYANATE POLYOL
R represents the portion of the organic molecule that can be varied depending
on the specific polyurethane that is being synthesised.
H H H
BUTYL BLADDER
N N O O N
R C R C R The bladder is the part of the ball in which
the air is contained. Butyl rubber is often
O O
n used because it retains the air better than the
POLYURETHANE other option, latex. However, latex bladders
(urethane linkages in orange) can provide better surface tension.
Polyurethane is a polymer - a very large

H CH3 H CH3 H
molecule built up from many smaller units
bonded together. The basic synthesis of C C C C C C
BUTYL
RUBBER
polyurethanes involves the addition reaction
of isocyanate and polyol molecules to form H CH3 H H H
n
urethane groups.

PHOTO BY - RENATOGIZZI (FLICKR.COM/NATOGIZZI) - SHARED UNDER A CREATIVE COMMONS BY NC LICENCE
BY NC ND
THE CHEMISTRY OF THE EURO 2016 BALL
POLYURETHANE COATING NYLON LINING
The surface covering of a football is composed Several layers of lining are used between the
of synthetic leather; in professional footballs, covering of the football and the bladder to
this is made from polyurethane polymers. improve the bounce and strength of the ball.
The Euro 2016 ball is made from a number This lining is made of nylon, another class of
of polyurethane panels, which are thermally polymers also known as polyamides. Polyesters
bonded together. This covering protects the can also be used for this purpose.
ball and minimises water absorption. In cheaper
footballs, the coating can be made from PVC.
O
H
N
N N O O N
C R C H R H H
O O O n
ISOCYANATE POLYOL NYLON 6-6
R represents the portion of the organic molecule that can be varied

depending on the specific polyurethane that is being synthesised.
BUTYL BLADDER
H H H
N N O O N
R C R C R The bladder is the part of the ball in which the
air is contained. Butyl rubber is often used
O O because it retains the air better than the other
n
option, latex. However, latex bladders can
POLYURETHANE provide better surface tension.
urethane linkages are shown in orange
H CH3 H CH3 H
Polyurethane is a polymer, a very large molecule
BUTYL
built up from many smaller units bonded C C C C C C RUBBER
together. The basic synthesis of polyurethanes
involves the addition reaction of isocyanate and H CH3 H H H
n m
polyol molecules to form urethane groups.
ration n:m = 0.985:0.015

THE CHEMISTRY OF THE WORLD CUP
THE BALL THE TROPHY
H
N
R
H
N
C
O
R
O
C
H
N
R
18-KARAT GOLD
O O
n MALACHITE BASE
POLYURETHANE
R represents variable portions of the polyurethane
6.1 kilograms, 36.8 centimetres high
The World Cup ball is made from six polyurethane The World Cup trophy is made of gold, though it is
panels which are thermally bonded together. hollow; if it were solid, it would be too heavy to lift!
Underneath this is a nylon lining, then the butyl The green base is made of malachite, which is a
rubber bladder which contains the air. copper carbonate hydroxide mineral.
THE SHIRTS THE VANISHING SPRAY

H H H H
O O
H C C C C H BUTANE
approx. 17%
H H H H
O O
POLYETHYLENE TEREPHTHALATE
n approx.
80%
approx.
1% ? approx.
2%
a type of polyester WATER SURFACTANTS OTHER
Football shirts are commonly made from The spray referees use as a temporary marker
polyesters. Elastane (also known as lycra) can be contains butane, which expands when released
incorporated to give strength and elasticity. Names from the can. Surfactants help create foam, which
and numbers are usually made of polyurethane. disappears as the butane evaporates.

THE COLOUR OF ALEXANDRITE
MAIN LOCATIONS
absorbance
ALEXANDRITE STRUCTURE
absorbance
chemical formula: Al2BeO4
= Al = BeO4 tetrahedra
CHROMIUM
Cr3+ Al3+ IMPURITIES
(occurs in <0.5% of aluminium sites)
ALEXANDRITE LIGHT TYPE LIGHT SPECTRUM

Alexandrite’s colour is formula: Al2BeO4 solid line: alexandrite absorbance
due to small amounts
of chromium impurities. Alexandrite appears blue-green in sunlight because not much blue or green
These cause it to absorb light is absorbed. In incandescent light, alexandrite appears purple-red; this
some colours of light while is because incandescent light contains a greater amount of red light than
others pass through. sunlight, as well as much less blue and green light.

COMPOSITIONS OF DIFFERENT ALLOYS
Alloys are materials composed of a mixture of elements including at least one metal, used as they often have superior properties to component elements. This
table shows the main elements found in a number of different alloys, and their common uses. Compositions can vary in cases, and this is merely an overview.
KEY AMALGAM BRASS BRONZE CAST IRON

Composition & trace elements MIN MAX MIN MAX MIN MAX MIN MAX MIN MAX MIN MAX MIN MAX MIN MAX
Hg 45% 55% Ag 22% 32% Cu 65% 90% Zn 10% 35% Cu 78% 95% Sn 5% 22% Fe 96% 98% C 2% 4%
Metal Non-metal
Major elements are given with MIN MAX MIN MAX Older compositions contained lead, Similar in composition to steel,
percentages. Minor elements are Sn 12% 30% Cu 12% 24% Pb but no longer used due to toxicity. Al Mn Ni Zn As P Si Si which has a lower carbon content.
given without percentages.
Alloy uses In older dental fillings, mining Decoration, plumbing, instruments Instruments, guitar strings, medals Metal structures & bridges
ELEMENTS KEY CUPRONICKEL GREEN GOLD MAGNALIUM MISCHMETAL

Ag Silver Mn Manganese MIN MAX MIN MAX MIN MAX MIN MAX
Mg
MIN MAX
Ce La
Cu 70% 90% Ni 10% 30% Au 75% Ag 6% 25% Cu Al 50% 95% 5% 50% 50% 25% Nd 15%
Al Aluminium Mo Molybdenum
Highly resistant to Archaically known as electrum. Appears Creates crackling Range of rare earth elements also present.
Mn Fe corrosion in seawater. as greenish-yellow, rather than green. Cu Ni Sn effects in fireworks Mixed with iron oxide to harden for flints.
As Arsenic Nd Neodymium
Coinage, marine engineering Core of Nobel prize medals Aircraft and car parts, fireworks Cigarette lighter flints
Au Gold Ni Nickel
Bi Bismuth P Phosphorus
NICHROME NITINOL NORDIC GOLD PEWTER
C Carbon Pb Lead MIN MAX MIN MAX MIN MAX MIN MAX MIN MAX
Ni 60% 80% Cr 15% 20% Ni 50% 55% Ti 45% 50% Cu 89% Al 5% Zn 5% Sn 85% 99% Cu Sb Bi
Ce Cerium Pd Palladium
Can be used for coils of Shape memory alloy; if deformed, its Despite the name, doesn’t Compositions used to commonly contain
Fe Mn Si electronic cigarettes. original shape is recovered on heating. Sn 1% contain any gold. lead, but no longer do due to toxicity.
Cr Chromium Pt Platinum
Cu Copper Sb Antimony Electric heaters, foam cutters Glasses frames 10, 20 and 50 cent Euro coins Decorative plates & vases
Fe Iron Si Silicon
SOLDER STEEL STERLING SILVER WHITE GOLD
Ge Germanium Sn Tin
MIN MAX MIN MAX
Sn 90% Ag 5% Cu 5% Fe 50% 99% C 0.1% 2.5% Ag 92.5% Cu Pt Ge Zn Au 75% Pd 10% Ni 10%
Hg Mercury Ti Titanium
Solder compositions previously contained Stainless steel: Must contain 92.5% silver; remainder is Often plated with rhodium
La Lanthanum V Vanadium lead, now discouraged due to toxicity. Cr Mn V Mo ~12% chromium other metals, usually copper. Zn 5% to enhance whiteness.
Mg Magnesium Zn Zinc
Joining electrical components Structures, cutlery, car bodies, rails Cutlery, jewelry, musical instruments Jewelry

THE NEW 12-SIDED £1 COIN
COMPOSITION
Cu
OUTER RING
NICKEL-BRASS Zn Ni
INNER RING Ni ?
NICKEL-PLATED ALLOY
The exact specification of the nickel-

plated alloy has not yet been revealed.
The new £1 coin arrives in the UK on 28th March 2017. One in thirty
£1 coins currently in circulation is a counterfeit; the new coin has
MASS: 8.75 GRAMS
security features that make it harder to counterfeit, including a THICKNESS: 2.8 MILLIMETRES
latent image that changes when viewed from different angles.
DIAMETER: 23.43 MILLIMETRES

C Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. Photo: The Royal Mint. BY NC ND
WEDDING RING METAL PROPERTIES
PLATINUM PALLADIUM WHITE GOLD YELLOW GOLD ROSE GOLD
Au Au Au
Pt Pd Pd Rh Ag Cu Cu Ag
Usually 95% platinum; iridium, ruthenium Usually 95% palladium. Other metals make Commonly an alloy of gold and palladium (or An alloy of gold with smaller amounts of An alloy of gold and copper, with smaller
and palladium are common alloying metals. up the remaining 5%, commonly ruthenium. platinum), plated with rhodium. copper and silver. amounts of silver.
HARDNESS (0-10) 4.0-4.5 HARDNESS (0-10) 4.8 HARDNESS (0-10) 2.5-4.0 HARDNESS (0-10) 2.5-4.0 HARDNESS (0-10) 2.5-4.0
DENSITY (g/cm3) 21.45 DENSITY (g/cm3) 12.02 DENSITY (g/cm3) 14.64 DENSITY (g/cm3) 15.58 DENSITY (g/cm3) 15.18
MELTING POINT (˚C) 1768 MELTING POINT (˚C) 1555 MELTING POINT (˚C) 943 MELTING POINT (˚C) 927 MELTING POINT (˚C) 902
VALUE ££££ VALUE £££ VALUE £££ VALUE £££ VALUE £££
RESIZEABLE? Yes RESIZEABLE? Yes RESIZEABLE? Yes RESIZEABLE? Yes RESIZEABLE? Yes
STERLING SILVER TITANIUM BLACK ZIRCONIUM TUNGSTEN CARBIDE STAINLESS STEEL
Ag Ti Fe
Cu
ZrO2 WC
V Al C Cr
Sterling silver must contain 92.5% silver. The Commonly made from a blend of titanium, Made by oxidising zirconium to produce a Alloyed with small amounts of cobalt so that An alloy of iron, carbon and other elements.
remainder is other metals, usually copper. vanadium and aluminium. black coating of zirconium oxide. the rings can be more easily shaped. Stainless steel contains min. 10.5% chromium.
HARDNESS (0-10) 2.5-3.0 HARDNESS (0-10) 6.0 HARDNESS (0-10) 7.5-8.0 HARDNESS (0-10) 8.5-9.0 HARDNESS (0-10) 5.0-6.5
DENSITY (g/cm3) 10.36 DENSITY (g/cm3) 4.506 DENSITY (g/cm3) 5.680 DENSITY (g/cm3) 15.63 DENSITY (g/cm3) 8.050
MELTING POINT (˚C) 893 MELTING POINT (˚C) 1668 MELTING POINT (˚C) 2715 MELTING POINT (˚C) 2870 MELTING POINT (˚C) 1370
VALUE ££ VALUE £ VALUE £ VALUE £ VALUE £
RESIZEABLE? Yes RESIZEABLE? No RESIZEABLE? No RESIZEABLE? No RESIZEABLE? No

WHY CAN LEAVES CAUSE RAIL DELAYS?
WHAT CAUSES THE PROBLEM? DEALING WITH LEAVES ON THE LINE
There are several potential explanations for the

lubricating effect of leaves on train tracks.
££
£50 MILLION
ESTIMATED COST PER YEAR IN THE UK TO CLEAR LEAVES FROM TRAINLINES
5,800 HOURS
ESTIMATED DELAYS IN THE UK CAUSED BY LEAVES ON TRAINLINES IN 2015
Leaves on the line cost rail companies millions every

year in delays and compensation. Below are some
Leaves can be compacted onto the tracks. The of the ways they deal with the problem.
1 compacted layer becomes thick enough to
prevent contact between wheels and rails.
High pressure water jets fitted to special trains
1 are used to blast leaf residue from tracks.
A chemical reaction between the leaf and the
LEAVES ON THE LINE 2 rail produces friction-reducing iron oxides.
1500 bar (22000 psi) pressure
Leaf residue on train tracks can reduce the friction COMPRESSED LEAF FILM
coefficient, μ. This leads to loss of grip between the FRICTION-REDUCING LAYER
train wheels and the track, meaning longer braking METAL RAIL Adhesion modifiers are applied after leaves
2 have been washed off to improve traction.
distances. Additionally, leaves on the line can
prevent signalling equipment detecting trains. Pectin in the leaves forms pectate gels with
3 iron from the steel in the rails, reducing friction.
ADHESION
μ = 0.40–0.65 MODIFIER
COOH OH COOCH3 OH
(SANDITE)
O O O O O SAND ALUMINIUM ADHESIVE
μ = 0.10–0.20 OH
O
OH OH
O
OH
O O
CH3 COOCH3 OH COOH
n In some countries lasers remove leaf films from
μ = 0.02–0.05 3
PECTIN (TYPICAL STRUCTURE)
rails (a process called laser ablation).

THE WINTER OLYMPICS MEDALS
2018
2018
2018
GOLD MEDAL SILVER MEDAL BRONZE MEDAL
Ag SILVER 580 g Ag SILVER 580 g Cu COPPER 444 g
The silver in this year’s medals

Au GOLD 6g has a purity of 99.9%. The gold Zn ZINC 49 g
and silver medals are the heaviest
in Olympic history; the bronze
The gold medal is mostly silver, medal is topped only by that at This year’s bronze medal is a
with a plated layer of gold on top. the 2010 Vancouver games. Cu90-Zn10 alloy.

PeriodicGraphics
C EN.ACS.O RG 29 FEB RUA RY 9, 20 15

Periodic graphics
More
online
To see more of
to compoundchem.
com. To see all of
JUNE 13, 2016 | CEN.ACS.ORG | C&EN 27

Periodic graphics
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online
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compoundchem.com.
visit cenm.ag/

Periodic graphics
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online
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compoundchem.com.
visit cenm.ag/
24 C&EN | CEN.ACS.ORG | JUNE 12, 2017

WORLD DIABETES DAY
As of 2014, around 387 million people worldwide have diabetes. What is the cause of this
disease, and what is the difference between the different types? Here, we take a brief look.
FOOD, BLOOD SUGAR, & INSULIN GLUCOSE

O O PANCREAS O O
O O
O O O O
O O O O
INSULIN
O
BLOOD BLOOD
SUGAR BLOODSTREAM SUGAR
O O
Eating food, particularly foods high in carbohydrates,
increases blood glucose levels. The hormone, insulin, is
O
secreted by the pancreas, and when released into the
bloodstream allows cells to take in the glucose and use it to
produce energy. Diabetes is a resistance to or lack of insulin. Hydrogen atoms on carbon implied –
each carbon has four bonds
TYPE 1 DIABETES TYPE 2 DIABETES GESTATIONAL DIABETES
PANCREAS PANCREAS O O O O
O O
O O O O
O O
INSULIN INSULIN INSULIN
BLOOD BLOOD
BLOODSTREAM BLOODSTREAM BLOODSTREAM SUGAR SUGAR
The immune system attacks The body becomes resistant High blood sugar levels
insulin-producing cells in to insulin’s effects, and can occur during 1 in 25
the pancreas, until it cannot its production eventually pregnancies. It usually
produce insulin, and it must decreases. Exercise and diet disappears after childbirth,
be injected instead. can help manage type 2. but can lead to type 2.

BY NC ND
A Rough Guide to
IARC CARCINOGEN CLASSIFICATIONS
The International Agency for Research on Cancer (IARC) classifies substances to show whether they are suspected to cause
cancer or not. It places substances into one of five categories depending on the strength of evidence for their carcinogenicity.
GROUP WHAT DOES IT MEAN? WHAT DOES IT INCLUDE?
CARCINOGENIC
GROUP TO HUMANS
1 Sufficient evidence in humans.

Causal relationship established.
Smoking, exposure to solar radiation,
alcoholic beverages and processed meats.
PROBABLY CARCINOGENIC
GROUP TO HUMANS
2A Limited evidence in humans.

Sufficient evidence in animals.
Emissions from high temp. frying, steroids,
exposures working in hairdressing, red meat.
POSSIBLY CARCINOGENIC
GROUP TO HUMANS
2B Limited evidence in humans.

Insufficient evidence in animals.
Coffee, gasoline & gasoline engine exhaust,
welding fumes, pickled vegetables.
CARCINOGENICITY
GROUP NOT CLASSIFIABLE
3 Inadequate evidence in humans.

Inadequate evidence in animals.
Tea, static magnetic fields, fluorescent
lighting, polyethene.
PROBABLY NOT ONLY 1 CHEMICAL EVER PLACED IN THIS

GROUP CARCINOGENIC 1 GROUP, OF ALL SUBSTANCES ASSESSED
4 Evidence suggests no
carcinogenicity in humans/animals
Caprolactam, which is used in the
manufacture of synthetic fibres.
THE IARC’S INDEX ONLY TELLS US HOW STRONG THE EVIDENCE IS THAT SOMETHING CAUSES CANCER.
SUBSTANCES IN THE SAME CATEGORY CAN DIFFER VASTLY IN HOW MUCH THEY INCREASE CANCER RISK.
COKE & DIET COKE: THE FACTS & THE FICTION
A couple of infographics on the effects Coke and Diet Coke have on your body have recently gone viral. Unfortunately, whilst some of the information
provided is correct, a lot of it is sensationalised, hyperbolic, or simply incorrect. Here, we sort the fact from the fiction to provide a clearer picture.
NORMAL COKE DOES CONTAIN 10 TEASPOONS OF SUGAR CAFFEINE DOESN’T STIMULATE PRODUCTION OF DOPAMINE
Caffeine isn’t directly involved in the production of dopamine, though it does help
to block its reabsorption. There’s no evidence that, at dietary levels, it affects
parts of the brain involved in addiction and reward, unlike heroin and cocaine.
A can of Coke contains 33 grams of sugar, around 9-10 teaspoons. Whilst this is
definitely a LOT of sugar, there’s no recommended daily allowance – though the
WHO suggests no more than 5% of total calories should come from added sugar.
CAFFEINE DOES HAVE A DIURETIC EFFECT IN THE BODY
Caffeine does increase urine output in doses equivalent to the amount found in
YOU WOULDn’T VOMIT IF NOT FOR THE PHOSPHORIC aCID 2-3 cups of coffee. However, it’s possible to develop a tolerance to this effect, and
it’s much diminished in those who consume caffeinated beverages regularly.
This claim is simply wrong. We’re capable of drinking sweetened beverages with
more than ten teaspoons of sugar, but no phosphoric acid, without vomiting.
CAFFEINE & ASPARTAME ISn’T A ‘POTENTIALLY DEADLY’ COMBINATION
ACIDIC BEVERAGES CAN DAMAGE YOUR TOOTH ENAMEL O
N
N O LEFT: CAFFEINE
O O OH O L to R:
HO OCH3 RIGHT: ASPARTAME
O O O N N N
HO PHOSPHORIC ACID H
HO P OH OH CITRIC ACID O NH2 O
HO OH MALIC ACID
OH OH O OH
The study cited by the graphic doesn’t even support this point. Aspartame is
Drinking a lot of acidic beverages, like Coke, could cause damage to your tooth much maligned, but numerous reviews have found it to be perfectly safe at normal
enamel over a long time. This isn’t limited to the phosphoric acid in Coke; fruit dietary levels. Of course, it’s all about moderation – anything is ‘potentially deadly’
juices, which contain citric and malic acids, can also cause erosion of tooth enamel. at a high enough dose, summed up by the phrase ‘the dose makes the poison’.
INSULIN SPIKES AREn’T THE MAIN CAUSE OF FAT PRODUCTION ASPARTAME DOESN’t ‘TRICK’ THE BODY INTO THINKING IT’S SUGAR
The fat production that is associated with sweetened drinks results more from the Aspartame tastes sweet, but doesn’t induce the same response in the body as
metabolism of fructose in the liver than an increase in the production of insulin. sugar does. It doesn’t lead to the production of insulin, as stated in the graphic.

C This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 licence. References: bit.ly/CokeDebunked BY NC ND
A Rough Guide to
TYPES OF SCIENTIFIC EVIDENCE
Being able to evaluate the evidence behind a claim is important, but scientiic evidence comes in a variety of forms. Here, the
diferent types of scientiic evidence are ranked and described, particularly those relevant to health and medicinal claims.
Anecdotal evidence is a person’s own personal

experience or view, not necessarily representative
... ANECDOTAL & of typical experiences. An expert’s stand-alone
opinion, or that given in a written news article, are
EXPERT OPINIONS both considered weak forms of evidence without
scientiic studies to back them up.
Animal research can be useful, and can predict

ANIMAL & CELL efects also seen in humans. However, observed
efects can also difer, so subsequent human trials
STUDIES
INCRE A SING S TRENGTH OF E VIDENCE
are required before a particular efect can be said

to be seen in humans. Tests on isolated cells can
(experimental)
also produce diferent results to those in the body.
A case report is a written record on a particular

CASE REPORTS & subject. Though low on the hierarchy of evidence,
they can aid detection of new diseases, or side
CASE SERIES efects of treatments. A case series is similar,
but tracks multiple subjects. Both types of study
(observational)
cannot prove causation, only correlation.
Case control studies are retrospective, involving

CASE-CONTROL two groups of subjects, one with a particular
condition or symptom, and one without. They then
STUDIES track back to determine an attribute or exposure
that could have caused this. Again, these studies
(observational)
show correlation, but it is hard to prove causation.
A cohort study is similar to a case-control study. It

COHORT involves selection of a group of people sharing a
certain characteristic or treatment (e.g. exposure
STUDIES to a chemical), and compares them over time to a
group of people who do not have this characteristic
(observational)
or treatment, noting any diference in outcome.
Subjects are randomly assigned to a test group,

RANDOMISED which receives the treatment, or a control group,
? CONTROLLED TRIALS
which commonly receives a placebo. In ‘blind’
trials, participants do not know which group they
are in; in ‘double blind’ trials, the experimenters do
(experimental)
not know either. Blinding trials helps remove bias.
Systematic reviews draw on multiple randomised

controlled trials to draw their conclusions, and
SYSTEMATIC also take into consideration the quality of the
REVIEW studies included. Reviews can help mitigate bias

in individual studies and give us a more complete
picture, making them the best form of evidence.
Note that in certain cases, some of these types of evidence may not be possible to procure, for ethical or other reasons.

LETHAL DOSES OF COMMON CHEMICALS
LD50 stands for ‘median lethal dose’, and is defined as the amount of a substance
LD50 required to kill 50% of a test population of animals, expressed in mg per kg of body
weight. Human LD50 values are calculated from these tests. For ethical reasons, tests
on animals to determine LD50 are being phased out in favour of other methods.
The figures provided below are median lethal doses, and are rough averages for a body weight of 75kg, when
the amount specified is taken all at once. Actual figures will vary depending on physical and medical condition.
WATER
6 LITRES
CAFFEINE
118 COFFEES
1 coffee = approx 240ml
(Or 175 shots of espresso)
ALCOHOL
13 SHOTS
Where 1 shot = 45 ml
(40% ABV)

References & further information: www.compoundchem.com/2014/07/27/lethaldoses BY NC ND
CHEMICAL COMPOUNDS IN CIGARETTE SMOKE
THIS GRAPHIC OFFERS A SUMMARY OF A SELECTION OF HAZARDOUS COMPOUNDS IN CIGARETTE SMOKE & THEIR EFFECTS
The compounds shown below are all found in cigarette smoke. The mass figures, given in µg, take
into account both mainstream (inhaled) and sidestream smoke. 1 µg is equal to 1 millionth of a gram.
Amounts of these compounds vary in different brands of cigarettes - these figures are approximate.
ESTIMATED NUMBER OF CHEMICAL
COMPOUNDS IN CIGARETTE SMOKE NICOTINE ACETALDEHYDE
∙ Approx. 919µg per cigarette ∙ Approx. 680-1571µg per cigarette
N ∙ Addictive O ∙ Known animal carcinogen
∙ Increases heart rate ∙ Probable human carcinogen
N ∙ Increases blood pressure ∙ Irritant to skin & eyes
∙ Increases blood glucose H3C H ∙ Irritant to respiratory tract
∙ Lethal dose: around 500-1000mg
7,357 N-NITROSAMINES
∙ Large class of compounds
1,3-BUTADIENE
R1 R2 ∙ Several are tobacco-specific ∙ Approx. 36-191µg per cigarette

N ∙ Known human carcinogens ∙ Known human carcinogen
∙ Most carcinogenic: NNK & NNN ∙ Suspected human teratogen
N ∙ NNK: approx. 0.3µg per cigarette ∙ Irritant to eyes & skin
O ∙ NNN: approx. 2-50µg per cigarette ∙ Irritant to upper respiratory tract
∙ May cause reproductive damage
70 BENZENE
∙ Approx. 46-272µg per cigarette
∙ Known human carcinogen
∙ Damages bone marrow
∙ Lowers red blood cell count
ACROLEIN
O
∙ Approx. 69-306µg per cigarette
∙ Possible human carcinogen
∙ Known DNA mutagen
∙ Irritant to skin & nasal passages
∙ May harm reproductive organs H ∙ May contribute to heart disease
AROMATIC AMINES POLYAROMATICS

NH2 ∙ Large class of compounds ∙ Large class of compounds
NUMBER OF THESE COMPOUNDS WITH ∙ Includes 2-aminonaphthalene: ∙ Includes benzo[a]pyrene:
- Known human carcinogen
CONFIRMED CARCINOGENIC ACTIVITY - Linked with bladder cancer
- Known human carcinogen
- Known DNA mutagen
- Approx. 0.04µg per cigarette - Affects reproductive capacity
- Up to 0.14µg per cigarette

A Rough Guide to
SPOTTING BAD SCIENCE
Being able to evaluate the evidence behind a scientific claim is important. Being able to recognise bad science reporting, or
faults in scientific studies, is equally important. These 12 points will help you separate the science from the pseudoscience.
1. SENSATIONALISED HEADLINES 7. UNREPRESENTATIVE SAMPLES USED

Article headlines are commonly designed to In human trials, subjects are selected that
entice viewers into clicking on and reading are representative of a larger population. If
Aa the article. At times, they can over-simplify

the findings of scientific research. At worst,
the sample is different from the population
as a whole, then the conclusions from the
trial may be biased towards a particular
they sensationalise and misrepresent them.
outcome.
2. MISINTERPRETED RESULTS 8. NO CONTROL GROUP USED

News articles can distort or misinterpret the In clinical trials, results from test subjects
findings of research for the sake of a good should be compared to a ‘control group’ not
story, whether intentionally or otherwise. If given the substance being tested. Groups
possible, try to read the original research, should also be allocated randomly. In
rather than relying on the article based on general experiments, a control test should
it for information. be used where all variables are controlled.
3. CONFLICTS OF INTEREST 9. NO BLIND TESTING USED

Many companies will employ scientists to To try and prevent bias, subjects should
carry out and publish research - whilst this not know if they are in the test or the
doesn’t necessarily invalidate the research, control group. In ‘double blind’ testing,
it should be analysed with this in mind. even researchers don’t know which group
Research can also be misrepresented for subjects are in until after testing. Note,
personal or financial gain. blind testing isn’t always feasible, or ethical.
4. CORRELATION & CAUSATION 10. SELECTIVE REPORTING OF DATA

Be wary of any confusion of correlation and Also known as ‘cherry picking’, this involves
causation. A correlation between variables selecting data from results which supports
doesn’t always mean one causes the other. the conclusion of the research, whilst
Global warming increased since the 1800s, x x ignoring those that do not. If a research
and pirate numbers decreased, but lack of paper draws conclusions from a selection
pirates doesn’t cause global warming. of its results, not all, it may be guilty of this.
5. UNSUPPORTED CONCLUSIONS 11. UNREPLICABLE RESULTS

Speculation can often help to drive science Results should be replicable by independent
forward. However, studies should be clear research, and tested over a wide range of
??? on the facts their study proves, and which conditions (where possible) to ensure they
conclusions are as yet unsupported ones. A are consistent. Extraordinary claims require
statement framed by speculative language extraordinary evidence - that is, much more
may require further evidence to confirm. than one independent study!
6. PROBLEMS WITH SAMPLE SIZE 12. NON-PEER REVIEWED MATERIAL

In trials, the smaller a sample size, the Peer review is an important part of the
lower the confidence in the results from scientific process. Other scientists appraise
that sample. Conclusions drawn can still be and critique studies, before publication
valid, and in some cases small samples are in a journal. Research that has not gone
unavoidable, but larger samples often give through this process is not as reputable,
more representative results. and may be flawed.

MEDICATIONS FOR LABOUR & BIRTH
INDUCTION OF LABOUR LABOUR PAINKILLERS
Most women go into labour after 42 weeks of pregnancy. Oxytocin is the natural hormone that dilates the cervix GAS & AIR
Sometimes labour is induced when a baby is overdue or and is responsible for contractions during labour. If
there are risks to the mother or baby’s health. contractions don’t start, or aren’t long enough or strong OXYGEN 50% Also known as entonox; can
enough, a synthetic oxytocin drip can be given. reduce pain and make it more
bearable. It can also make you
NITROUS OXIDE 50%
PESSARY TABLET GEL feel woozy and light-headed.
O O
H O
O
N
N NH2 OPIOIDS
H
O NH O
HO HN O N Injections of opioids such as
O
O pethidine or diamorphine can
H2N O
All of these induction methods contain prostaglandins, be given to relieve (but not
natural hormones that ‘ripen’ the cervix and induce S NH PETHIDINE eliminate) pain during labour.
S O NH2
labour. All three require insertion into the vagina.
O O N
O H EPIDURAL
DINOPROSTONE H2N N H
N N
H N
An epidural is an injection of
O O O
O OH OXYTOCIN
drugs around the nerves in the
spine that carry pain signals
BUPIVACAINE
from the uterus. It is usually a
mix of a local anaesthetic, such
Medication brand names include syntocinon and pitocin
as bupivacaine, and an opioid,
FENTANYL such as fentanyl. The pain relief
Oxytocin alone, or combined with ergometrine (a is usually very effective, leaving
O
combination named ‘syntometrine’), can be given to most women pain-free, though
HO OH mothers in the third stage of labour to aid delivery of the
N N
it can take up to 40 minutes for
placenta and stop blood loss after birth. the full effect to kick in.
Prostaglandin commonly used in labour induction

IMPROVING STABILITY OF CONE SNAIL TOXINS FOR THERAPEUTIC USE
WHAT ARE CONE SNAIL TOXINS?
Conotoxin peptides are the toxic
components of the venom of fish-
hunting cone snails. Some make
muscles relax by binding to nACh
receptors, giving them possible uses
in anaesthesia. Many others are of
interest as drugs to control pain and
treat other medical conditions.
CONOTOXIN nACh MUSCLE
PEPTIDE RECEPTORS RELAXANT
S S STABILITY PROBLEMS
Conotoxins have poor stability in blood

H E C C N P A C G R H Y S C NH2 and this can limit their potential to be
used as drugs. Reaction of the disulfide
bridges can cause the shape of
S S conotoxins to change. This means the
peptides can no longer bind to their
targets to produce medical effects.
KEY: E C C amino acid chain S S disulfide bridge
N IMPROVING STABILITY
N
N One of the disulfide bridges in
alpha-conotoxin GI can be replaced
with a 1,2,3-triazole bridge. This
H E C X N P A C G R H Y S X NH2
mimics the shape and arrangement
of the disulfide bridge. It is also more
stable and tests in human cells
S S showed that, with the 1,2,3-triazole
N bridge shown in place, GI is held in
N the correct shape to retain its full
KEY: S S disulfide bridge N triazole bridge biological activity.
WHY THIS RESEARCH MATTERS S S
The modification of GI was easily

achieved with commercially available N
reagents and could be used with other N
peptides, including other conotoxins, N
containing disulfide bridges to make
more stable compounds for medical
use. In addition, the NMR method used
to determine GI’s structure could inform
future drug discovery efforts.
SYNTHESISE REPLACE POTENTIAL
PEPTIDE BRIDGES DRUG USE
α-Conotoxin GI Triazole-Peptidomimetics: Potent and Stable Blockers of a Human Acetylcholine Receptor – DOI: 10.1039/C8SC04198A
A Knuhtsen, C Whitmore, F S McWhinnie, L McDougall, R Whiting, B O Smith, C M Timperley, A C Green, K I Kinnear, A G Jamieson
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30 C&EN | CEN.ACS.ORG | SEPTEMBER 17, 2018

SNOWDROPS, ALZHEIMER’S, & CHEMICAL WARFARE
POISONOUS SNOWDROPS NERVE AGENT POISONING
Snowdrops contain poisonous alkaloids, Acetylcholine (ACh) is released by nerve

including galantamine and lycorine, endings, and controls contraction of of
particularly in their bulbs. Ingestion can muscles when it binds to receptors.
cause vomiting and diarrhoea.
H3C
O N ACh ACh ACh
N
H
LYCORINE
O
H
GALANTAMINE
HO
OH O OCH3
HO
H The enzyme acetylcholinesterase (AChE)
controls ACh levels by breaking it down.
TREATING ALZHEIMER’S Organophosphate (OP) nerve agents stop
H3C this, causing convulsions and death.
Falling levels of the neurotransmitter N AChE OP AChE OP

AChE ACh
acetylcholine are linked to symptoms of AChE
Alzheimer’s disease. Galantamine stops an ACh ACh ACh
enzyme (acetylcholinesterase) breaking

down acetylcholine, increasing availability.
normal with organophosphate
ALZHEIMER’S
O CH3
O OCH3
CH3 HO Galantamine also latches on to AChE and
N+ acetylcholine
H stops it working, but does so reversibly.
H3C O CH3
GALANTAMINE This blocks the nerve agents from binding
ACETYLCHOLINE (ACh) acetylcholine
to it irreversibly and prevents poisoning.
GALANTAMINE

23RD JANUARY – GERTRUDE B. ELION’S BIRTHDAY
GERTRUDE b. ELION
1988
BORN
23 January 1918 Elion was jointly awarded the 1988 Nobel
Prize in Physiology or Medicine for work
DIED on the development of a number of
drugs, based on biochemical differences
21 February 1999 between human and pathogen cells.
S HN NH2
Working both alone and O2N
with George Hitchings, H N OCH3
N S N
Elion discovered new N
drugs against a variety N H2N N OCH3
of diseases. Her name N N N N
N OCH3
appears of 45 different H
patents and she was
awarded 25 honarary
doctorates.
MERCAPTOPURINE AZATHIOPRINE TRIMETHOPRIM
first treatment for leukemia to prevent transplant rejection antibiotic
O O Cl N
OCH3
N O N
NH HO
N
NH N N
N
HO N N NH2
N N O HO OH
H H2N N NH2 NH2
ALLOPURINOL ACICLOVIR PYRIMETHAMINE NELARABINE

treatment for gout antiviral for herpes infections for malaria and toxoplasmosis treatment for cancer

BY NC ND
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A BRIEF GUIDE TO DOPING IN SPORTS
Doping in sports has been in the news in the run up to the Olympics. What drugs will doping tests at the Olympics be looking
for? This graphic looks at some of the major groups of drugs used in doping, their effects, and why athletes might take them.
ANABOLIC AGENTS STIMULANTS HORMONES AND MODULATORS
OH
MUSCLE MASS & STRENGTH HO
! ALERTNESS AND ENERGY
H3C
CH3 O AFFECT HORMONES/METABOLISM
H CH3 N+
HO N H3C N O–
H H
74 nO. OF NAMED BANNED AGENTS H 66 nO. OF NAMED BANNED AGENTS H 20 nO. OF NAMED BANNED AGENTS
OH
O
TESTOSTERONE
48% % OF POSITIVE TESTS IN 2014
ADRENALINE
MELDONIUM
The largest class of prohibited drugs, and the most Stimulants are used to improve alertness, attention, A range of drugs which generally interfere with human
commonly detected. Anabolic steroids mimic the and energy. Many behave similarly to the hormones hormones. They can be used with anabolic steroids,
hormone testosterone, increasing muscle mass and adrenaline and noradrenaline. They include to suppress some of the undesirable effects of these
physical strength. This class also includes some non- amphetamines. Taking them can increase blood drugs. Some affect oestrogen levels in the body,
steroidal drugs. They have a range of side effects. pressure and cause cardiac problems. whereas others affect human metabolism.
DIURETICS
PRESSURE
AND OF
MASKING
REACTION
AGENTS SURFACE NARCOTICS
AREA OF REACTANTS OTHER
USE
BANNED
OF A CATALYST
SUBSTANCES
O HO O OH
H HELP TO CONCEAL DOPING INCREASE PAIN TOLERANCE ERYTHROPOIETIN (EPO) BETA-BLOCKER DRUGS
N Cl
O
HO H HO
O
OH
S 22 ALCOHOL (IN-COMPETITION) GLUCOCORTICOSTEROIDS

HO
nO. OF NAMED BANNED AGENTS CAN HELP REDUCE ANXIETY H

H
NH2 O
O O N
H3C
FUROSEMIDE
MORPHINE
11 No. OF NAMED BANNED AGENTS CANNABIS & CANNABINOIDS BETA-2 AGONIST DRUGS
Diuretics remove fluids from the body and can be This class includes narcotic analgesics such as Many more substances are banned, including EPO,
used by athletes to regulate their body mass, as well as morphine and codeine which can be enhance which promotes red blood cell production, getting
diluting urine so lower levels of banned substances are performance by increasing a competitor’s tolerance oxygen to muscles more effectively. Some substances,
registered in tests. Masking agents are drugs taken to to pain. They can also reduce anxiety which can be such as alcohol and beta-blockers, are only prohibited
conceal the presence of illegal drugs in urine samples. advantageous in some sports. in-competition for some sports.

CANNABIS & SYNTHETIC CANNABINOIDS
In recent years, the use of synthetic cannabinoids as a substitute for cannabis has been on the increase. However, there is also some concern about their
potential effects on users. This graphic looks at what synthetic cannabinoids are, how they can be classified, and some of the effects that they can have.
CANNABIS & CANNABINOIDS SELECTED CLASSES OF SYNTHETIC CANNABINOIDS

HO R1
O OH
H OH OH
N
R2
O R2 R R1
O
H ∆-9-TETRAHYDROCANNABINOL CLASSICAL AMINOALKYLINDOLES NON-CLASSICAL
(structure similar to THC) (number of subcategories) (e.g. cyclohexylphenols)
Cannabis contains a large number of different cannabinoid
chemicals. The main psychoactive constituent in cannabis is the
cannabinoid tetrahydrocannabinol (THC). It acts on cannabinoid
receptors in the brain, causing a range of psychological effects.
R4
O R3 O
O
N R2 N N
N R3 R4
R3 R2 R2 R1 R2 R1
R1 R1
SYNTHETIC CANNABINOIDS & THEIR EFFECTS

NAPHTHOYLINDOLES NAPHTHYLMETHYLINDOLES PHENYLACETYLINDOLES BENZOYLINDOLES
e.g. JWH-018 e.g. JWH-175 e.g. JWH-167 e.g. RCS-4
2-100x
Synthetic cannabinoids can be classified in a number of ways. Broadly,
they can be split into three groups: classicial cannabinoids, which are
SYNTHESIS ILLICIT USE IN ‘SPICE’ HIGH POTENCY SERIOUS SIDE EFFECTS structurally related to THC; aminoalkylindoles, the most numerous,
First synthesised in labs in the Sprayed onto dried herbs then Synthetic cannabinoids can be Adverse effects often much which can be further split into a number of subclasses; and non-classical,
1980s for research purposes. smoked or ingested. much more potent than THC. more severe than for THC. including cyclohexylphenols and other compounds. Other classifications
split them into further groups. A group not shown here is the eicosanoids.
Synthetic cannabinoids (SCs) were never intended for human consumption, but synthesised to investigate
potential medicinal uses of cannabis. They target the same receptors, but have a higher efficacy than THC. A number of the compounds have ‘code names’. JWH stands for John W.
There is no published safety data for the compounds, and little is known about their effects in humans. Many Huffman, who synthesised many new cannabinoids. Others have more
are controlled substances, but modifications of the compounds produces new entities not covered by legislation. obscure origins; AKB-48 is named after a Japanese girl band, whilst XLR-
Use of SCs is linked with nausea & vomiting, anxiety, psychosis, seizures, acute renal failure, and in cases, death. 11 is named after the first liquid rocket fuel developed in the US.

MAJOR CLASSES OF ANTIDEPRESSANT DRUGS
Key: ‘FIRST GENERATION’ ANTIDEPRESSANTS ‘SECOND GENERATION’ ANTIDEPRESSANTS NOTE: DESIGNATIONS ARE ARBITRARY - DIFFERENT SOURCES CAN GROUP THEM DIFFERENTLY
MONOAMINE OXIDASE INHIBITORS (MAOI s) TETRACYLIC & UNICYCLIC ANTIDEPRESSANTS SSRI s

THE FIRST CLASS OF MODERN ANTIDEPRESSANTS PRIMARILY COMPOUNDS THAT DON’T FIT OTHER CLASSES SELECTIVE SEROTONIN REUPTAKE INHIBITORS
NH O
H F
HN
N F
N
NH2 NH2 N F Cl
N Cl
H O N
H
O Cl
Cl
Phenelzine (Nardil) Tranylcypromine (Parnate) Amoxapine (Asendin) Bupropion (Wellbutrin) Fluoxetine (Prozac) Sertraline (Zoloft)
EXAMPLES EXAMPLES EXAMPLES

Iproniazid (discontinued), phenelzine (Nardil), isocarboxazid (Marplan), Bupropion (Wellbutrin), mirtazapine (Remeron), amoxapine (Asendin), Fluoxetine (Prozac), sertraline (Zoloft), citalopram (Celexa), paroxetine (Paxil),
tranylcypromine (Parnate), selegiline (Emsam), moclobemide (Amira). maprotiline (Ludiomil). fluvoxamine (Faverin), escitalopram (Lexapro).
DETAILS DETAILS DETAILS
Inhibit monoamine oxidase, preventing breakdown of neurotransmitters. Variably inhibit serotonin & norepinephrine reuptake. Some poorly understood. Inhibit reuptake of serotonin. High toxic dose and mild side effects.
Rarely used due to toxicity and potentially lethal food & drug interactions. Bupropion is amongst the few antidepressants without sexual side-effects. The most widely prescribed antidepressants in many countries.
FIRST APPROVED 1950 1960 1970 1980 1990 2000
TRICYCLIC ANTIDEPRESSANTS (TCAs) SARIs SNRIs

DOMINANT CLASS UNTIL INTRODUCTION OF SSRIs SEROTONIN ANTAGONIST & REUPTAKE INHIBITORS SEROTONIN-NOREPINEPHRINE REUPTAKE INHIBITORS
N
N
N N
O
N N O N OH OH
Cl N N
O OH
N
N N
N N NH Cl N N
Cl
Imipramine (Tofranil) Chloripramine (Anafranil) Nortriptyline (Aventyl) Trazodone (Desyrel) Etoperidone (Axiomin) Venlafaxine (Efexor) Desvenlafaxine (Pristiq)
EXAMPLES EXAMPLES EXAMPLES
Chloripramine (Anafranil), imipramine (Tofranil), nortriptyline (Aventyl), Trazodone (Desyrel), etoperidone (Axiomin), lorpiprazole (Normarex), Venlafaxine (Efexor), desvenlafaxine (Pristiq), duloxetine (Cymbalta).
lofepramine (Lomont), amitriptyline (Tryptomer). mepiprazol (Psigodal), nefazodone (Serzone).
DETAILS
DETAILS DETAILS Inhibit both serotonin & norepinephrine reuptake. Studies have shown they
Inhibit reuptake of neurotransmitters; mostly epinephrine, and serotonin. Prevent reuptake of serotonin, as well as stopping it binding to cell receptors. may have a modest increase in efficacy compared to SSRIs. They also have
Due to side effects and potential for fatal overdose, now seldom used. Nefazodone can be toxic to the liver and is no longer commonly prescribed. slightly milder side effects.

BY NC ND
TARGETING DNA REPAIR TO COMBAT CANCER CHEMORESISTANCE
WHAT IS A CANCER CELL? DNA DAMAGE
CELL BECOMES
DORMANT
The cells in our body are continually
dividing; when they do, their DNA
unzips and replicates, producing
two copies. The copy isn’t perfect so
HEALTHY CELL DAMAGED DNA PRECANCEROUS CELL DEATH
small changes can accumulate. CELL
In cancer, these changes have
broken the control over cell division,
meaning they divide constantly and
uncontrollably, causing problems. CANCEROUS
CELL
DNA REPAIR
H H
TARGETING CANCER’S DNA
H H
Cl N N
H
H H
Most cancer treatments target cancer
Pt cell DNA. They include radiotherapy
H H N
H
N (beams of high energy) and
Pt H H Pt
N
H
chemotherapy (anti-cancer drugs).
H H H
Cisplatin is one of the most common
Cl N chemotherapy drugs; it reacts with
H H DNA, forming a platinum bridge
between the strands. This prevents the
DNA from unzipping and replicating,
and in turn prevents the cancer cell
MAJOR INTRASTRAND MINOR INTERSTRAND from making new copies of itself.
CISPLATIN CROSSLINK CROSSLINK
DNA AND CHEMORESISTANCE 1 2 3
C G G A A C G G A A C G G A A
MISMATCH
Our DNA has a number of repair G U C T T G C T T G C C T T REPAIR
mechanisms that remove damaged
sections of DNA. Cancer cells ERROR CORRECT
exploit these repair mechanisms to
remove replication blocks created 1 2 3
by chemotherapy. This means

C G G A A C G G A A C G G A A
increasingly high doses of the drugs NUCLEOTIDE
are needed to destroy the cancer, and G C T T T G T G C C T T
EXCISION REPAIR
sometimes even this is not enough.
ERROR CORRECT
COMBATING CHEMORESISTANCE O
OLAPARIB AND FUTURE DRUGS
OLAPARIB
Our understanding of DNA repair can N H Olaparib works by trapping PARP
help us to combat cancer. Scientists onto DNA, preventing it from
N
have found that cancer cells often O completing its repair. There is a
become dependant on a particular good chance that cancers that are
repair mechanism, and this is an PARP-dependent can be treated
N
Achilles’ heel that can be targeted with Olaparib. Scientists are now
to kill the cancer. One example is N developing new drugs to block more
F
Olaparib, an inhibitor of the DNA DNA repair processes to treat a wider
repair protein called PARP. O range of cancers.
Based on materials provided by Tom Fleming, www.browngroupnucleicacidsresearch.org.uk.

Synthesis for Biology and Medicine CDT, www.oxfordsynthesiscdt.ox.ac.uk, University of Oxford.
This work was supported by The Royal Commission of 1851.
© Andy Brunning 2017

CHEMUNICATE www.compoundchem.com/chemunicate
A BRIEF SUMMARY OF DISINFECTANTS & ANTISEPTICS
Key: USED FOR ANTISEPSIS USED TO DISINFECT SURFACES USED FOR STERILISATION (E.G. MEDICAL INSTRUMENTS) USED FOR PRESERVATION
ALCOHOLS ALDEHYDES BIGUANIDES BISPHENOLS DIAMIDINES

USED IN ALCOHOL-BASED SANITARY HAND MAINLY USED FOR DISINFECTION & USED IN CREAMS & FOR SKIN ANTISEPSIS TRICLOSAN IS COMMONLY USED IN MAINLY USED FOR THE TOPICAL
GELS PRESENT IN HOSPITALS STERILISATION OF MEDICAL INSTRUMENTS IN SURGICAL PROCEDURES ANTISEPTIC SOAPS TREATMENT OF WOUNDS
Cl
O H H H
NH NH
Cl OH
OH O N N N
N
H
N
H
N
H
O
NH NH
NH NH
Cl
OH H O H2N NH2
OH OH O OH OH O
H H HO
OH
HO
OH
Cl Cl
O O
H OH OH OH OH
ETHANOL ISOPROPANOL FORMALDEHYDE GLUTARALDEHYDE CHLORHEXIDINE DIGLUCONATE TRICLOSAN PROPAMIDINE
Kill many bacteria and fungi, and some Show broad activity against bacteria, fungi, Slow-acting, but don’t evaporate easily like Effective against bacteria, though more so Less commonly used than the other featured
viruses, when used at suitably high and viruses. Not used for general antisepsis, alcohols, so provide some residual activity. against gram-positive bacteria. There are compounds; halogenated derivatives of
concentrations (usually 60-90% solution). due to their high toxicity. Due to the relatively Active against most bacteria, and show concerns surrounding triclosan’s use in these compounds can also be used. Unlike
Slow-acting, and evaporate easily, so lack long contact times required to disinfect, other some activity against fungi and viruses. soaps due to its effects on the skin, and also some other agents, they still work in the
residual action. Can’t be used to sterilise. agents are often preferred. Combination with alcohol increases efficacy. due to its accumulation in the environment. presence of organic matter.
HALOGEN-RELEASING METAL DERIVATIVES PEROXYGENS PHENOLICS QUATERNARY AMMONIUM SALTS

MAINLY USED FOR SURFACE DISINFECTION; RARELY USED FOR DISINFECTION, BUT SUITABLE CONCENTRATIONS CAN BE USED USED FOR SURFACE DISINFECTION IN USED IN MANY ANTISEPTIC CREAMS AND
FOUND IN HOUSEHOLD BLEACH CAN BE USED FOR VACCINE PRESERVATION FOR STERILISATION & ANTISEPSIS HOSPITALS AND LABORATORIES KITCHEN SURFACE CLEANERS
O O– Na+ OH
CnH2n+1
- O H O OH
O N+
Na+ Cl I I -
N+ -
Ag+ S
Hg
O O OH H3C CH3 Cl–
O O H O
SODIUM HYDROGEN
IODINE SILVER NITRATE THIOMERSAL PERACETIC ACID PHENOL o-PHENYLPHENOL BENZALKONIUM CHLORIDE
HYPOCHLORITE PEROXIDE
Affect bacteria, viruses, and fungi. Usually Silver salts are strongly bactericidal, and Widely used and environmentally friendly, Phenol is no longer used as it is corrosive Low toxicity, so can be used to disinfect
chlorine and iodine-containing compounds, can be used to halt bacterial growth in burn as they decompose into safe by-products; and carcinogenic. A number of derivatives surfaces in food-handling areas. Work
with the halogens acting as oxidising agents wounds. Thiomersal is used as a preservative most solutions need stabilisers to prevent are widely used, often for sterilising against gram positive bacteria and gram
on micro-organisms. Iodine solutions can in some vaccines, and there are no causative decomposition. Broad spectrum of activity. surfaces. They’re partly responsible for the negative bacteria, though gram negative
cause irritation and staining. links to any harmful effects. Peracetic acid is the more potent. characteristic smell of hospitals. bacteria growth in solutions is possible.

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BY NC ND
A BRIEF SUMMARY OF INTRAVENOUS ANAESTHETICS
Key: B BARBITURATE BD BENZODIAZEPINE A ARYLCYCLOHEXAMINE I IMIDAZOLE P ALKYL PHENOL RAPID-ACTING AGENTS SLOWER-ACTING AGENTS
AMOBARBITAL B THIAMYLAL B DIAZEPAM BD ETOMIDATE I PROPOFOL P
ALONG WITH OTHER BARBITURATES, LIKE OTHER BARBITURATES, STRONG BUT MORE COMMONLY KNOWN BY ITS FREQUENTLY USED FOR ANAESTHESIA FOR HAS LARGELY REPLACED THIOPENTAL FOR
PREVIOUSLY USED AS A ‘TRUTH SERUM’ SHORT-ACTING BRAND NAME, VALIUM EMERGENCY INTUBATION INDUCTION OF ANAESTHESIA
O Cl O
O OH
NH NH N
O O
N
O S N
NH NH N
O O
Intermediate duration of action. It is a Very short duration of action. Thiamylal is still Long duration of action. In its use as an anti- Fairly short duration of action. Used as Short duration of action. Widely used
hypnotic agent, and can be used to treat in current use as an induction agent, and is anxiety medication it has been nicknamed an induction agent for short surgical for both induction and maintenance of
insomnia. It was also used by the US army also used as an anti-convulsant to limit the ‘Mother’s Little Helper’. In anaesthesia, it is procedures; the chances of a large drop in anaesthesia, and often given with opioids to
in WWII as an attempted treatment for shell side effects experienced from the use of often used to induce moderate sedation. blood pressure are lower than for other help ease pain. Awakening is rapid and can
shock, but proved largely ineffective. other anaesthetics. Also used for benzodiazapine dependence. anaesthetics. No longer used very widely. also be accompanied by mild euphoria.
1929 1934 YEAR AVAILABLE FOR CLINICAL USE 1950 1957 1966 1973 1977 1978
THIOPENTAL B METHOHEXITAL B KETAMINE A LORAZEPAM BD MIDAZOLAM BD
PREVIOUSLY USED FOR LETHAL LOWERS SEIZURE THRESHOLD; USEFUL FOR ALSO USED AS A RECREATIONAL DRUG ALSO USED FOR SHORT-TERM TREATMENT REPLACED THIOPENTAL FOR USE IN
INJECTIONS IN THE USA ELECTROCONVULSIVE SHOCK THERAPY OF ANXIETY LETHAL INJECTIONS IN THE USA
O O Cl Cl
NH
HN O NH N
NH N
O
S O
NH N N N
Cl OH
O O Cl F
Very short duration of action. Its use in lethal Very short duration of action, and faster Short duration of action. Doesn’t suppress Long duration of action. Often used to Short duration of action. Midazolam is two to
injections was ceased after the EU banned its recovery rate than with some other breathing as much as other anaesthetics, but treat anxiety disorders under the brand three times as potent as diazepam, and has a
export for this purpose. Used as an induction barbiturates. Also cheaper than propofol. can also cause hallucinations. Often used to name ‘Ativan’. Sometimes given before faster onset. Also used in end-of-life care to
agent to induce loss of consciousness, but Commonly used for outpatient surgical and induce and maintain anaesthesia in severely awake procedures as it can also prevent the help reduce agitation and anxiety, and in the
largely replaced by propofol. dental procedures. injured patients. formation of new memories. management of seizures.

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BY NC ND
COMMON COMPONENTS OF VACCINES
As well as the active components, vaccines contain a number of other substances. This graphic examines these and the reasons for their inclusion.
ACTIVE COMPONENTS STABILISERS

A form of the virus, bacteria or toxin that causes the disease OH OH Vaccines need to be storable, so stabilisers
is used as the antigen. This antigen is modified from the OH are added to ensure the various components
HO
original form so it no longer causes disease, but still elicits remain stable and effective. A variety of
an immune response from the body. To modify the disease- OH OH different stabilisers are used; either inorganic
causing agent, it can be treated with specific chemicals, SORBITOL magnesium salts such as magnesium sulfate
so it cannot replicate. It can also be treated so it does not or magnesium chloride, or mixtures of lactose,
cause serious disease, or only parts of the disease-causing MgSO4 sorbitol and gelatin. Monosodium glutamate
agent that do not cause serious symptoms can be used. and glycine are also used in some cases.
MAGNESIUM SULFATE
ADJUVANTS PRESERVATIVES
Added to enhance the body’s immune response O O- Na+
Al(OH)3 to the vaccine. How they work isn’t entirely OH
understood, but it’s thought they help keep S
ALUMINIUM HYDROXIDE Hg
antigens near the site of injection. This means they OH
can be easily accessed by the immune system cells. O
AlPO4 There is no evidence of any serious adverse effects THIOMERSAL PHENOL PHENOXYETHANOL
ALUMINIUM PHOSPHATE from adjuvants, though they can cause some minor
reaction near the injection site. Preservatives help prevent contamination of vaccines. They are used
particularly in multi-dose vaccines. Thiomersal is a common preservative,
though its use declined in the late 1990s when vaccines were falsely linked
to child autism. This link was later shown to be an elaborate medical hoax,
ANTIBIOTICS and there is no link between thiomersal and autism.
H HO NH2 HO
N O O
NH2
OH
O
H2N NH2
O
HO
O
O O
O
H2N
OH TRACE COMPONENTS
H2N H2N OH OH
OH
O O N
H
O These are left-over from the vaccine production process.
NH2 OH OH NH2
Though they are purposefully removed, residual
GENTAMICIN NEOMYCIN
amounts remain. Formaldehyde is one such agent,
Antibiotics are used in the manufacturing process of the vaccine to
prevent bacterial contamination. They are later removed, and only residual
H H used to deactivate viruses and detoxify bacteria, but
amount remaining is several hundred times lower than
quantities remain in the vaccine after the production process. FORMALDEHYDE the smallest amount known to cause harm in humans.

THE CHEMISTRY OF FOXGLOVES
The vibrance of foxgloves belies their poisonous nature; but the same compounds that make them poisonous can also be used in medicine.
POISONOUS FOXGLOVES FOXGLOVES IN MEDICINE
O O
Though poisonous in large amounts, in small doses
DIGOXIN digoxin can be used to manage some heart conditions,
OH
including abnormal heart rhythms and heart failure.
It increases the force of the heart’s contraction and
H consequently the volume of blood pumped with each
HO O O
O O beat, and also causes the heartbeat to slow.
H OH
HO O HO O
H
OH
Na+ SODIUM ION CONCENTRATION
All parts of the foxglove contain compounds called

1 Ca2+ CALCIUM ION CONCENTRATION
cardiac glycosides, including the structurally
similar digoxin and digitoxin. Ingestion of these
compounds can cause nausea, vomiting, diarrhoea,
and an irregular heart beat. They disable cell sodium- FORCE OF CONTRACTION
potassium ion pumps, leading to increased cell sodium
and calcium ion concentration. This slows the heart
rate, which can lead to a heart attack and death.
2 VOLUME OF BLOOD PER BEAT
HEART RATE
O
DIGITOXIN
O
0.8–2.0
Nanograms per
THERAPEUTIC
RANGE
>2.0
Nanograms per
TOXIC
LEVEL
millilitre of blood millilitre of blood
H
HO O O
O O The therapeutic levels of digoxin don’t differ greatly
H OH
from those at which toxic effects are seen, and as such
HO O HO O dosages must be carefully monitored.
H
OH

THE CHEMISTRY OF ORAL CONTRACEPTIVES
The first oral contraceptive, norethindrone, was synthesised by Carl Djerassi in 1951. This graphic looks at the range of compounds used and how they work.
THE NATURAL HORMONES PROGESTogeNS

O HO HO
OH
H H H H
H H
H H H H
H H H H
O O
HO O
NORETHINDRONE LEVONORGESTREL
ESTRADIOL PROGESTERONE
Can be used in combination with estrogens, but also on their own
Oral contraceptives contain synthetic versions of two hormones in progestogen-only pills. These pills must be taken continuously
produced naturally by the body: estrogens and progestogens. and within 3 hours of a specific time every day. Recommended for
Both hormones have roles in the female menstrual cycle. breast-feeding women, as it doesn’t affect milk production.
HOW ORAL CONTRACEPTIVES WORK ESTROGENS

HO
H
H
OH
LH HO HO
MAINTAIN CONSISTENT
FSH
SUPPRESS RELEASE OF PREVENTS H
H
H H
H
H
HORMONE LEVELS OTHER HORMONES OVULATION
HO O
Steady levels of estrogens and/or progestogens in the body as a
result of oral contraceptives trick the pituitary gland into thinking a ETHYNYL ESTRADIOL MESTRANOL
woman is already pregnant, stopping it from releasing hormones
that stimulate ovulation, and preventing pregnancy. Progestogens Combined oral contraceptive pills include an estrogen as well as
promote formation of a thicker layer of cervical mucus, which
makes it difficult for sperm to reach the uterus, and also affect
the uterine lining and make it harder for an egg to attach.
99.9% EFFECTIVE a progestrogen. Most are taken over a 28 day cycle, with 21 pills
taken, followed by a week of no pills. They must be taken within
12 hours of a specific time every day to maximise protection.
( WHEN TAKEN CORRECTLY)
THE CHEMISTRY OF THROAT LOZENGES
Throat lozenges are commonly used to provide relief from a sore throat. This graphic takes a look at some of the compounds used, and how they exert their efects.
COMBATTING SORE THROATS

HO OH HO OH
Cl Cl
LEFT TO RIGHT: AMYLMETACRESOL, DICHLOROBENZYL ALCOHOL, & HEXYLRESORCINOL
Many lozenges for sore throats contain either amylmetacresol or dichlorobenzyl

alcohol - or both compounds in combination. They have an antiseptic efect,
and have been shown to act on bacterial (and even some viral) infections.
Hexylresorcinol, used in some lozenges, also has a mild anaesthetic efect.
Though they are efective in relieving the symptoms of sore throats, there is
mixed evidence for them reducing the duration of infection.
HOW DO LOZENGES COMBAT SORE THROATS? OTHER COMPOUNDS

Other compounds can also be included in lozenges. Flavouring agents
are used to make them palatable; sometimes menthol is used for
this purpose as it can also impart a ‘cooling’ efect, as well as having
Na+ anaesthetic properties of its own. Compounds with decongestant and
anti-coughing efects can also be included in the formulations.
THROAT LOZENGES SODIUM CHANNELS SORENESS O
TAKEN BLOCKED REDUCED O
O
As well as their antiseptic efects, it’s been postulated that all three of the H N
compounds mentioned above can bind to and block sodium channels, stopping HO
H
H2N
pain signals reaching the brain. This leads to them having an anaesthetic-like
efect, comparable to the potency of some anaesthetic compounds. LEFT TO RIGHT: MENTHOL, DEXTROMETHORPHAN (COUGH SUPPRESSANT), & BENZOCAINE (ANAESTHETIC)

UNDERSTANDING THE DRUG DISCOVERY PROCESS
The process of discovering, testing, and eventually gaining approval for selling a drug is a long and arduous one. Here, we look at the different
stages involved, and the approximate length of time that each stage takes, to eventually arrive at an approved drug that can be given to patients.
1 2 3 4
RESEARCH & DEVELOPMENT PRECLINICAL STUDIES CLINICAL TRIALS REVIEW & APPROVAL
3–6 YEARS 1 YEAR 4–7 YEARS 1–2 YEARS

Drug development begins long before clinical Up to 10,000 compounds considered during Clinical trials involve human participants. These If a drug is deemed effective in clinical trials, it is
testing. It starts with the identification of a target screening, but only around 250 will make it to tests in volunteers provide information on safety submitted to regulating bodies to be approved.
for a drug to act on, then the identification of preclinical testing. Efficacy and potential risks are and efficacy. Around 70% of drugs succeed in It’s estimated that only around 1 in 5000 drug
compounds that could potentially hit that target. evaluated before human trials can begin. phase 1, 33% in phase 2, and 25–30% in phase 3. candidates makes it all the way to approval.
TARGET IDENTIFICATION IN VITRO STUDIES PHASE 1 TRIALS EVALUATION
WHAT WILL THE DRUG AFFECT? LATIN FOR ‘IN GLASS’ USUALLY 20–80 PEOPLE EVIDENCE FROM TRIALS
Understandings of the causes of diseases or Laboratory experiments on cells or molecules The primary goal of phase 1 trials is to determine The regulating body reviews the evidence
conditions can help researchers know what outside of their usual biological surroundings. the drug’s side effects. Additionally, how quickly provided by the pharmaceutical company for
processes or pathways drugs to treat the This gives some idea of efficacy against the the drug is metabolised and excreted from the the drug’s efficacy and safety. Drugs offering
condition need to be able to target. identified target. Toxicity can also be assessed. body can be determined during these trials. important advances are given priority.
COMPOUND SCREENING IN VIVO STUDIES PHASE 2 TRIALS APPROVAL & MANUFACTURE
UP TO 10,000 COMPOUNDS LATIN FOR ‘IN THE LIVING’ USUALLY 100–300 PEOPLE ~75% SUBMISSIONS APPROVED
Compounds are screened in laboratory tests for Drugs that look promising in in vitro testing will Phase 2 trials help to determine how effective If the benefits of taking the drug are deemed
their ability to affect the identified target. They progress to testing in animals. These include tests the drug is in patients who have the condition it to outweigh its risks, it is approved. The cost of
are also screened to check they don’t interfere on toxicology, efficacy, and how quickly the drugs is trying to treat. Controlled trials compare the developing a drug that gains marketing approval
with other related targets. are absorbed and subsequently eliminated. effects of the drug to that of a placebo. is estimated to be $2,558 million.
LEAD IDENTIFICATION REQUIRED STANDARDS PHASE 3 TRIALS POST-RELEASE MONITORING

WHICH COMPOUNDS TO TEST? MIN. 2 MAMMALIAN SPECIES USUALLY 1,000–3,000 PEOPLE INDEFINITE DURATION
Though screening is unlikely to uncover a perfect Drugs must undergo toxicity testing on at least Gauges efficacy, dosage, and safety in a larger After a drug is approved and available for use by
drug candidate, promising compounds can be two mammals (one non-rodent), including at population. Also compares efficacy to existing patients, it is still monitored for any side effects
identified. The structures of these molecules can least two administration routes, before they are treatments, as well as interactions with other in the general population that may not have
be modified to try and improve their activity. allowed to proceed to clinical trials in humans. drugs and effects of different dosages. occurred in the drug’s clinical trials.

WORLD TUBERCULOSIS DAY
24 March is World Tuberculosis Day. In this graphic, we take a look at the basics of the disease, and how it can be treated.
WHAT IS TUBERCULOSIS? FIRST LINE TB DRUGS TREATING DRUG RESISTANT TB

1/3 OF THE WORLD IS INFECTED WITH O OH
DRUG-RESISTANT TUBERCULOSIS
LATENT TB N
NH2
H3C
H
N
H N CH3 TB bacteria that are resistant to at
10% OF LATENT TB N H
CASES PROGRESS TO least one first line TB drug.
OH
MYOBACTERIUM TUBERCULOSIS ACTIVE TB ISONIAZID (INH) ETHAMBUTOL (EMB)
MULTIDRUG-RESISTANT TUBERCULOSIS
Tuberculosis (TB) is a bacterial disease which usually O
affects the lungs. In many cases it is symptomless HO
N NH2 O Resistant to more than one anti-TB
(latent TB), but can progress to active disease which H3C
N
OH
OH OH
O drug and at least INH and RIF.
kills around half of those affected if left untreated. O
NH
O
N
PYRAZINAMIDE (PZA) O N
1.8 MILLION 95% OF DEATHS RIFAMPICIN (RIF)

O
CH3
CH2
OH N Tuberculosis that is resistant to first line drugs must
be treated with second line drugs. These can include
DEATHS IN 2015 IN DEVELOPING COUNTRIES drugs that are usually less effective, which have toxic
Active TB is treated by taking several antibiotics side effects, or which are unavailable in developing
for six to nine months. The four drugs shown are countries. Streptomycin was formerly considered a
WHAT ARE THE SYMPTOMS? commonly used first line drugs in treatment regimes. first line drug, but is now used less due to increased
cases of resistance to its effects.
SELECTED SECOND LINE DRUGS O
HO O HO OH
HO
COUGHING WEIGHT LOSS CHEST PAINS STREPTOMYCIN O NH2

DIVIDES EVERY 15-20 HOURS ANTIBIOTIC RESISTANCE HO O O N
NH2
HO HN N OH
CYCLOSERINE
ZZ
Myobacterium tuberculosis divides more slowly than H2N NH2
Z most bacteria, making development of antibiotic CAPREOMYCIN

resistance more likely. In addition, the mycolic acids in
STREPTOMYCIN
its cell wall limit the effectiveness of some antibiotics. AMIKACIN
FATIGUE FEVER LOSS OF APPETITE

A BRIEF GUIDE TO SELECTED COMMON PAINKILLERS
THERE ARE TWO MAIN CLASSES OF PAINKILLERS - PARACETAMOL IS AN EXCEPTION. Key: N NON-STEROIDAL ANTI-INFLAMMATORY DRUGS P PARACETAMOL O OPIOID ANALGESICS
N
ASPIRIN N
IBUPROFEN O
TRAMADOL O
MORPHINE O
HYDROMORPHONE O BUPRENORPHINE
MORE COMMONLY PRESCRIBED POTENTIAL FOR SERIOUS SIDE METABOLISED IN THE BODY TO A THE FIRST INDIVIDUAL PLANT MOSTLY USED INTRAVENOUSLY IN ALSO COMMONLY USED TO TREAT
FOR BLOOD CLOT PREVENTION EFFECTS LESS THAN OTHER NSAIDS MORE POTENT OPIOID ALKALOID EVER ISOLATED A HOSPITAL SETTING OPIOID DEPENDENCE
O OH N N N
O H
O H HO
O
OH
O H
O OH N HO OH HO O O O
HO OCH3
Salicylate drug A phenylpropanoic acid Synthetic opioid Naturally-occurring opioid Semi-synthetic opioid Semi-synthetic opioid
TRADE NAMES TRADE NAMES TRADE NAMES TRADE NAMES TRADE NAMES TRADE NAMES
Aspirin, Acuprin, Ecotrin Advil, Nurofen, Motrin, Brufen Ryzolt, Tramal, Ultram MS Contin, Oramorph, Sevredol Palladone, Dilaudid Suboxone, Subutex, Zubsolv
Inhibits cyclo-oxygenase enzymes, Exact mode of action unknown. Binds to opioid receptors in the Precise mechanism unknown; binds Precise mechanism unknown; binds Precise mechanism unknown; binds
(COX) preventing formation of However, it is known to inhibit COX central nervous system, & inhibits to opioid receptors in the central to opioid receptors in the central to opioid receptors in the central
prostaglandins and reducing enzymes, and thus the formation of noradrenaline & serotonin reuptake, nervous system responsible for nervous system responsible for nervous system. Also has potent
inflammation & pain. prostaglandins. inhibiting pain transmission. transmitting pain. transmitting pain. local anaesthetic properties.
0.003 0.008 0.03 POTENCY (VS. MORPHINE) 0.1 1 1.5 5 4-7 40 80-100
P
PARACETAMOL O
CODEINE O
HYDROCODONE O
OXYCODONE O
METHADONE O
FENTANYL
A.K.A ACETAMINOPHEN, OR THE MOST WIDELY USED OPIATE IN AROUND 99% OF WORLDWIDE ONE OF THE MOST ABUSED COMMONLY USED TO PREVENT OFTEN USED FOR PAIN RELIEF
TYLENOL IN THE USA THE WORLD SUPPLY CONSUMED IN THE USA PRESCRIPTION OPIOIDS HEROIN WITHDRAWAL SYMPTOMS DURING SURGICAL PROCEDURES
OH N N N N
O
O H H HO
N N
O
N
H O O OH O O O
H3CO O O
Antipyretic analgesic Naturally occurring opioid Semi-synthetic opioid Semi-synthetic opioid Synthetic opioid Synthetic opioid
TRADE NAMES TRADE NAMES TRADE NAMES TRADE NAMES TRADE NAMES TRADE NAMES
Acetaminophen, Tylenol, Panadol Co-codamol (with paracetamol) Vicodin (with paracetamol) Roxicodone, OxyContin, Oxecta Methadose, Dolophine, Symoron Actiq, Durogesic, Abstral
Mode of action not well understood; Precise mode of action unknown; Precise mode of action unknown; Precise mode of action unknown; Precise mode of action unknown; Precise mode of action unknown;
it’s thought it may act in a similar binds to opioid receptors in the binds to opioid receptors in the binds to opioid receptors in the binds to opioid receptors in the binds to opioid receptors in the
manner to aspirin, but also have central nervous system responsible central nervous system responsible central nervous system responsible central nervous system responsible central nervous system responsible
effects in the brain. for transmitting pain. for transmitting pain. for transmitting pain. for transmitting pain. for transmitting pain.
Note: Potency values are for oral administration. Numeric measures of potency are variable; the figures given are merely general approximations, and can be affected by a number of factors.

BY NC ND
A BRIEF SUMMARY OF INHALATIONAL ANAESTHETICS
A RANGE OF SIMPLE BUT DIVERSE CHEMICAL COMPOUNDS WITH GENERAL ANAESTHETIC PROPERTIES. Key: C CURRENTLY CLINICALLY UTILISED R RARELY OR NO LONGER IN USE
NITROUS OXIDE C CHLOROFORM R TRICHLOROETHENE R HALOTHANE R ENFLURANE C DESFLURANE C
ALSO KNOWN AS LAUGHING GAS PRODUCED BY MANY KINDS DYED BLUE TO AVOID CONFUSION ONLY INHALATIONAL ANAESTHETIC RAPID INDUCTION & RECOVERY BOILS AT ROOM TEMPERATURE;
OF SEAWEED WITH CHLOROFORM CONTAINING A BROMINE ATOM FROM ANAESTHESIA LOW POTENCY
N N+ O- Cl Cl Cl F F
F
F F O F O
Cl Br Cl F
-
N N +
O Cl Cl Cl F
F F F F F F
Colourless gas with a slightly sweet Colourless, sweet-smelling and Colourless, non-flammable liquid, with Colourless liquid with a sweet odour Volatile, colourless liquid, with a sweet Colourless, non-flammable liquid, with
odour and taste dense liquid a sweet smell resembling that of chloroform smell; light-sensitive an unpleasant, pungent odour
Like other inhalational anaesthetics, Common in the 1800s, its use was When used as an anaesthetic it was Unstable in light. A potent Used increasingly in the 1970s and Highest onset and offset of action
it also induces a degree of analgesia. abandoned due to toxicity & fatalities. almost always combined with nitrous anaesthetic, though it is a weak 80s, but no longer as common. It of the volatile anaesthetic drugs.
It is a weak general anaesthetic, so is Contrary to popular belief, it’s hard to oxide. It smells similar to chloroform, analgesic. Hepatitis links resulted lowers the threshold for seizures in However, it has a low potency, and
often used as a carrier gas for other, incapacitate someone quickly with a which it replaced, but was itself in a dramatic reduction in use, & epilepsy sufferers, and can also be its high cost prohibits its use in less
more powerful anaesthetics. chloroform-soaked rag. replaced by faster acting agents. replacement with newer agents. toxic to the kidneys. developed countries.
1844 1846 1847 YEAR AVAILABLE FOR CLINICAL USE 1925 1930 1951 1956 1960 1973 1981 1992 1994
DIETHYL ETHER R CYCLOPROPANE R FLUOROXENE R METHOXYFLURANE C ISOFLURANE C SEVOFLURANE C
COMMONLY USED AS A SOLVENT EXTREMELY REACTIVE UNDER THE FIRST VOLATILE ANAESTHETIC SIGNIFICANT RESPIRATORY STRUCTURAL ISOMER OF NAME DERIVES FROM THE SEVEN
NORMAL CONDITIONS CONTAINING FLUORINE DEPRESSANT ENFLURANE FLUORINE ATOMS IT CONTAINS
Cl F F
F F
F F
F O F O
O O Cl F F
O F
F F
F F F Cl F
Colourless, volatile and highly Colourless and highly flammable gas Colourless liquid, with a less pungent A colourless liquid with a strong, fruity Colourless, non-flammable liquid, with Colourless, non-flammable liquid, with
flammable liquid with a sweet, petrol-like odour smell than diethyl ether aroma and high boiling point a pungent, musty odour a mildly unpleasant sweet odour
Also known simply as ‘ether’, it was Often combined with oxygen, and Compared to other agents available Extremely potent, but with slow Always administered with oxygen; Most commonly used volatile
commonly used with chloroform gave a rapid onset of anaesthesia. at the time, fluoroxene, whilst of onset and offset times, and also a nitrous oxide can also be used. anaesthetic, often administered with
or alcohol. It was found to have However, its high cost and explosive use, did not provide any distinct powerful analgesic. Abandoned in Often used to maintain anaesthesia nitrous oxide & oxygen. Its onset &
undesirable side-effects, such as nature limited its use, leading to it advantages, although it did appear to 1970s due to kidney toxicity, but still induced with another drug. Its use is offset are slower than desflurane, but
nausea and vomiting. being largely phased out. minimise respiratory irritation. used in emergencies in Australia. beginning to decline. it irritates mucous membranes less.

BY NC ND
DIFFERENT CLASSES OF ANTIBIOTICS - AN OVERVIEW
Key: COMMONLY ACT AS BACTERIOSTATIC AGENTS, RESTRICTING GROWTH & REPRODUCTION COMMONLY ACT AS BACTERICIDAL AGENTS, CAUSING BACTERIAL CELL DEATH
ß-LACTAMS AMINOGLYCOSIDES chloramphenicol glycopeptides quinolones oxazolidinones

MOST WIDELY USED ANTIBIOTICS FAMILY OF OVER 20 ANTIBIOTICS COMMONLY USED IN LOW INCOME COMMON ‘DRUGS OF LAST RESORT’ RESISTANCE EVOLVES RAPIDLY POTENT ANTIBIOTICS COMMONLY
IN THE NHS O
COUNTRIES OH
USED AS ‘DRUGS OF LAST RESORT’
NH2
O O
R O O
F O
H H HO O HO OH
OH
F
N HO
OH N+
HO O OH
S O NH2 - O
O O HO
O O Cl H
O HO O O N O O
N N N
N
N O
N NH2 Cl HO OH
HO HN N OH N O
Cl
O O HN
O H O
H
N
H
N
O
O N N N
OH H2N NH2 Cl OH NH
H
O
H
H2N O
H
HN
HO
O All contain fused aromatic rings with a All contain 2-oxazolidone somewhere
Distinct individual compound O
carboxylic acid group attached in their structure
All contain a beta-lactam ring All contain aminosugar substructures HO OH OH
MODE OF ACTION
EXAMPLES EXAMPLES Consist of carbohydrate linked to a EXAMPLES EXAMPLES
Inhibits synthesis of proteins,
Penicillins (shown) such as Streptomycin (shown), neomycin, peptide formed of amino acids Ciprofloxacin (shown), levofloxacin, Linezolid (shown), posizolid,
preventing growth.
amoxicillin and flucloxacillin; kanamycin, paromomycin. trovafloxacin. tedizolid, cycloserine.
EXAMPLES
Cephalosporins such as cefalexin. No longer a first line drug in any
MODE OF ACTION Vancomycin (shown), teicoplanin. MODE OF ACTION MODE OF ACTION
developed nation (except for
MODE OF ACTION Inhibit the synthesis of proteins by conjunctivitis) due to increased Interfere with bacteria DNA Inhibit synthesis of proteins by
MODE OF ACTION
Inhibit bacteria cell wall biosynthesis. bacteria, leading to cell death. resistance and worries about safety. replication and transcription. bacteria, preventing growth.
Inhibit bacteria cell wall biosynthesis.
DISCOVERY 1930 1940 1950 1960 1970 1980
sulfonamides tetracyclines macrolides ansamycins streptogramins lipopeptides

FIRST COMMERCIAL ANTIBIOTICS BECOMING LESS POPULAR DUE TO SECOND MOST PRESCRIBED CAN ALSO DEMONSTRATE TWO GROUPS OF ANTIBIOTICS THAT INSTANCES OF RESISTANCE RARE
WERE SULFONAMIDES DEVELOPMENT OF RESISTANCE ANTIBIOTICS IN THE NHS ANTIVIRAL ACTIVITY ACT SYNERGISTICALLY HO O
O
O O
OCH3 O N
OH O OH O O H
O H
OH NH OH
H2N
O NH HN
O
OH
HO OH H3CO OH NH O NH
NH2 OH
H2N S N C2H5 O O
HO
O
N
CH3 O
O O
O
O O O
HN O HN
OH O NH2 O OH
H H H OCH3 O O
O N O H H
O OH N
O O
HN H3CO NH2 O
C9H19
O
N
N
H
O
N
N
H
OH O OO
HN O
OH
CH3 OH N
O NH
O O O NH O
All contain the sulfonamide group All contain 4 adjacent cyclic All contain a 14-, 15-, or 16-membered
hydrocarbon rings All contain an aromatic ring bridged by Combination of two structurally differing NH2
macrolide ring
EXAMPLES an aliphatic chain. compounds, from groups denoted A & B
All contain a lipid bonded to a peptide
Prontosil, sulfanilamide (shown), EXAMPLES EXAMPLES EXAMPLES EXAMPLES
sulfadiazine, sulfisoxazole. Tetracycline (shown), doxycycline, Erythromycin (shown), Geldanamycin (shown), rifamycin, Pristinamycin IIA (shown),
EXAMPLES
limecycline, oxytetracycline. clarithromycin, azithromycin. Daptomycin (shown), surfactin.
MODE OF ACTION naphthomycin. Pristinamycin IA.
Do not kill bacteria but prevent their MODE OF ACTION MODE OF ACTION MODE OF ACTION
MODE OF ACTION MODE OF ACTION
growth and multiplication. Cause Inhibit synthesis of proteins by Inhibit protein synthesis by bacteria, Disrupt multiple cell membrane
Inhibit the synthesis of RNA by Inhibit the synthesis of proteins by
allergic reactions in some patients. bacteria, preventing growth. occasionally leading to cell death. functions, leading to cell death.
bacteria, leading to cell death. bacteria, leading to cell death.

BY NC ND
HAY FEVER & HAY FEVER MEDICATIONS
THE CAUSE ANTIHISTAMINES FOR HAY FEVER SODIUM CROMOGLYCATE IN EYE DROPS
O Cl O O
O Na-+ O O -
Na+
N OH O OH O
N O O O O
O
CETIRIZINE N
TREE, GRASS & WEED POLLENS
O
LORATADINE
The percentage of the UK N SODIUM CROMOGLYCATE
10-15% population affected by hay
fever. Cl
The percentage of hay fever
Prevents release of histamine
90-95% sufferers that are allergic to
grass pollens. Block histamine action, Commonly used in eye drop solutions, sodium
prevent most symptoms cromoglicate prevents hay fever symptoms by
stabilising mast cells, and preventing them from
THE ALLERGIC RESPONSE
releasing histamine. Unlike anti-histamines, it
All oral formulations for treatment of hay fever
Pollen exposure results in the are antihistamines. These bind to H1 histamine is effective at remedying itchy eyes even after
1 body misidentifying it as a threat;
antibodies are released to combat it.
receptors instead of histamine, preventing the symptoms have started.
effects produced by the allergic response -
although they may not clear blocked noses.
The antibodies produced bind to two CORTICOSTEROIDS
2 types of cell in tissues - mast cells
and basophils. 1ST GENERATION VS. 2ND GENERATION
O
These release several chemicals, O
3 including histamine, which produce First generation antihistamines can cause HO

O O O
Prevent the
an inflammatory response. undesireable effects, including sedation.
Second generation are less likely to exhibit
NASAL H inflammatory
sedative effects, particularly loratadine. Peak SPRAY
4
Symptoms of this response include
a runny nose, itching, sneezing fits, levels of antihistamines are generally reached
Cl H symptoms of
and nasal congestion. O
one hour after taking.
BECLAMETASONE
hay fever
N
HN Take when hay fever symptoms are expected, Prevent nasal symptoms more effectively than
NH2 rather than when they have already started. antihistamines, and also relieve itchy eyes. They act
to reduce inflammation, rather than directly blocking
This is because they cannot reverse the effects of histamine or preventing the action of histamine.
HISTAMINE already binding to the H1 receptors, and so will not provide relief.

TEIXOBACTIN - A NEW ANTIBIOTIC
Teixobactin is the first member of a new class of antibiotics - and, more importantly, the method used to discover it could lead to many more.
O NH2
HOW TEIXOBACTIN WAS DISCOVERED
O O OH
H H H
N N N
HN N N Soil
H H Sample taken Single soil
O O O and diluted bacterium in
O OH HN O each CHANNEL SOIL
HN O
NH O O A DEVICE REFERRED TO By RESEARCHERS AS THE ‘iCHIP’ WAS USED TO CULTURE SOIL BACTERIA
ALLOWING NUTRIENTS & SIGNAL MOLECULES TO PASS TO THE BACTERIA & STIMULATE GROWTH.
Teixobactin O NH HN Bacteria themselves produce antibacterial compounds to kill off competing
bacteria, but 99% of these bacteria cannot be grown in a lab. The discovery
One of 25 new antibiotic compounds discovered of teixobactin is actually less important than the method used to discover it;
using a new method, and considered the most O researchers used a device that allowed them to dilute the bacteria-containing
promising. The compound is toxic to bacteria, soil samples, sandwich them between two semi-permeable membranes, then
but not to the cells of mammals. It works against HN immerse them in soil, allowing the bacteria to be grown in the lab; a method
gram-positive bacteria, such as MRSA, but not which could eventually lead to many more potential antibiotic candidates.
gram-negative bacteria such as E. coli. NH
HN
HOW TEIXOBACTIN WORKS LIMITATIONS OF TEIXOBACTIN

Teixobactin has a unique mechanism of action, targeting lipid molecules
bacteria use to build their cell walls. As it’s hard for bacteria to alter these
molecules, it’s expected to take much longer for resistance to develop.
ONLY TESTED IN MICE TRIALS TAKE TIME LIKELY INJECTION ONLY NOT VS. ALL BACTERIA
BINDS TO PREVENTS BACTERIA
LIPIDS CELL WALL SYNTHESIS Teixobactin human trials are yet to begin; approval could take several years. It
doesn’t work against bacteria with an extra membrane around their cell wall.

THE CHEMISTRY OF ASTHMA INHALERS
Asthma medication commonly comes in two different colours of inhalers: blue and brown. Though these colours can vary, usually the
medication can be classed as either a ‘reliever’ or a ‘preventer’. The identity and function of the chemical compounds in each vary.
RELIEVERS PREVENTERS
HO
HO
O
O
HO HO
N H
O
H H
OH
H H
O
SALBUTAMOL BUDESONIDE
(also known as albuterol in the US) (sold under trade name Pulmicort)
TWO 5-20 2-8 4-6

HOURS MINS DAYS WEEKS
Bronchodilator Short-acting Mean Duration Maximal Effect Anti-inflammatory Long-acting Onset of Action For Peak Effect
Relievers, such as salbutamol, are taken for the immediate relief of Preventers help asthma sufferers by acting to reduce inflammation
asthma symptoms. They cause the airways to widen by relaxing the and keep their airways open. They are commonly steroids, and are
muscles in the lungs. Usually, they are taken ‘nebulised’ - that is, turned only useful for prevention - they won’t provide any relief if you are
into a fine mist that is then inhaled - and their action is apparent after already experiencing an asthma attack. It has to be taken daily, and
a short amount of time, making them of great use in cases of asthma its full effects are not reached for several weeks. Though there are
attacks. Salbutamol is commonly marketed as Ventolin. several different drugs used as preventers, they all function similarly.

Ci ASTHMA INHALER IMAGE: Stuart B, https://www.flickr.com/photos/gnu2000/5602664050 BY NC ND
THE CHEMISTRY OF DECONGESTANTS
Nasal decongestants are commonly used to provide relief from a blocked nose; this graphic looks at how they work, and some commonly used compounds.
PSEUDOePHEDRINE OXYMETAZOLINE
OH
H HO N
N
HN
Duration: around 8 hours. Duration: around 7 hours.

Regulated in some countries due to use as Can also be used as a drug to treat nose
precursor for methamphetamine. bleeds and eye redness.
PHENYLEPHRINE XYLOMETAZOLINE HOW THEY WORK

Decongestants ease nasal congestion by reducing the
OH swelling of blood vessels in the nose. They do this by
H N acting on receptors to constrict the blood vessels in
HO N the tissue that lines the nasal cavity.
HN Decongestants are available in the form of both
nasal sprays and tablets; nasal sprays tend to exhibit
a quicker onset of action. However, they can also
Duration: around 4 hours. Duration: around 5-6 hours. lead to ‘rebound congestion’, with use of more than
Alternative to pseudoephedrine, though Like the other decongestants, use isn’t advised a few days worsening congestion when use of the
studies conflict as to its efficacy. for those with high blood pressure. decongestant is stopped.

TRIAL DRUGS FOR TREATMENT OF THE EBOLA VIRUS
TRIALS ON THREE DIFFERENT EBOLA TREATMENTS WILL BEGIN IN WEST AFRICA IN DECEMBER, INCLUDING TWO ANTI-VIRAL DRUGS, CHOSEN DUE TO PROMISING DATA & NON-PROHIBITIVE
COSTS. FOR ETHICAL REASONS, NO CONTROL GROUP WILL BE USED IN TRIALS, AND THEY WILL END AHEAD OF SCHEDULE IF IMPROVEMENT TO 40% MORTALITY IS OBSERVED.
NH2
N
O
O N F N
OH
NH2
O
O P
O O
N OH
HO
The Ebola Virus Brincidofovir Favipiravir

70% WEST AFRICAN DEATH RATE Anti-viral originally developed to treat Anti-viral, active against a range of RNA
smallpox, adenovirus, and cytomegalovirus. viruses including influenza & yellow fever.
5000+ DEATHS SINCE OUTBREAK Tests on cells in a lab have suggested Appears effective in a mouse model of the
Brincidofovir could help treat ebola virus. ebola virus.
Effects of the Virus The first US patient given it at a late stage

died, but another patient was subsequently
passed ebola-free.
Reported that its administration aided the
recovery of a French nurse in Liberia, but its
efficacy in human cases is still unclear.
NAUSEA VOMITING DIARRHOEA RED EYES Mechanism unclear - not usually effective Works by blocking replication of the virus by
RASH CHEST PAINS STOMACH PAINS against RNA-based viruses like ebola. inhibiting an enzyme.
SEVERE WEIGHT LOSS BLEEDING & BRUISING Safety tested in 1000+ human subjects. In Already in phase III clinical trials in the US for
phase III clinical trials for other viruses in US. flu virus treatment.
LOSS OF BLOOD FROM ORIFICES DEATH
Ci EBOLA VIRUS IMAGE: PUBLIC LIBRARY OF SCIENCE JOURNAL (http://www.plosbiology.org/article/info:doi/10.1371/journal.pbio.0030403) BY NC ND
A GUIDE TO THE TWENTY COMMON AMINO ACIDS
AMINO ACIDS ARE THE BUILDING BLOCKS OF PROTEINS IN LIVING ORGANISMS. THERE ARE OVER 500 AMINO ACIDS FOUND IN NATURE - HOWEVER, THE HUMAN GENETIC CODE
ONLY DIRECTLY ENCODES 20. ‘ESSENTIAL’ AMINO ACIDS MUST BE OBTAINED FROM THE DIET, WHILST NON-ESSENTIAL AMINO ACIDS CAN BE SYNTHESISED IN THE BODY.
Chart Key: ALIPHATIC AROMATIC ACIDIC BASIC HYDROXYLIC SULFUR-CONTAINING AMIDIC NON-ESSENTIAL ESSENTIAL
O O
Chemical O O O O
Structure O H3N O O
O
O
(at physiological pH) O NH2
single letter NH3 NH3 NH3
NH3
code
NAME A Alanine A Glycine G ISOLEUCINE I LEUCINE L PROLINE P VALINE V

three letter code Ala Gly Ile Leu Pro Val
DNA codons GCT, GCC, GCA, GCG GGT, GGC, GGA, GGG ATT, ATC, ATA CTT, CTC, CTA, CTG, TTA, TTG CCT, CCC, CCA, CCG GTT, GTC, GTA, GTG
H
O N
O O O O O
NH2 O H
O O N
O NH3 O O O H2N N O O
NH3 H
NH3 NH3
HO
O NH3 NH3 HN NH3
O
O
PHENYLALANINE F TRYPTOPHAN W TYROSINE Y ASPARTIC ACID D GLUTAMIC ACID E ARGININE R HISTIDINE H

Phe Trp Tyr Asp Glu Arg His
TTT, TTC TGG TAT, TAC GAT, GAC GAA, GAG CGT, CGC, CGA, CGG, AGA, AGG CAT, CAC
O OH O O O O
O O O
H3N S H2N
O HO O O HS O O O H2N O
NH3 O NH3 NH3
NH3 NH3 NH3
NH3
LYSINE K SERINE S THREONINE T CYSTEINE C METHIONINE M ASPARAGINE N GLUTAMINE Q

Lys Ser Thr Cys Met Asn Gln
AAA, AAG TCT, TCC, TCA, TCG, AGT, AGC ACT, ACC, ACA, ACG TGT, TGC ATG AAT, AAC CAA, CAG
Note: This chart only shows those amino acids for which the human genetic code directly codes for. Selenocysteine is often referred to as the 21st amino acid, but is encoded in a special manner.
In some cases, distinguishing between asparagine/aspartic acid and glutamine/glutamic acid is difficult. In these cases, the codes asx (B) and glx (Z) are respectively used.

BY NC ND
A GUIDE TO THE TWENTY COMMON AMINO ACIDS
AMINO ACIDS ARE THE BUILDING BLOCKS OF PROTEINS IN LIVING ORGANISMS. THERE ARE OVER 500 AMINO ACIDS FOUND IN NATURE - HOWEVER, THE HUMAN GENETIC CODE
ONLY DIRECTLY ENCODES 20. ‘ESSENTIAL’ AMINO ACIDS MUST BE OBTAINED FROM THE DIET, WHILST NON-ESSENTIAL AMINO ACIDS CAN BE SYNTHESISED IN THE BODY.
Chart Key: ALIPHATIC AROMATIC ACIDIC BASIC HYDROXYLIC SULFUR-CONTAINING AMIDIC NON-ESSENTIAL ESSENTIAL
O O O
Chemical O O O
Structure OH H2N OH OH OH OH
OH
single letter NH2 NH2 NH NH2
code
NH2
NAME A Alanine A Glycine G ISOLEUCINE I LEUCINE L PROLINE P VALINE V

three letter code Ala Gly Ile Leu Pro Val
DNA codons GCT, GCC, GCA, GCG GGT, GGC, GGA, GGG ATT, ATC, ATA CTT, CTC, CTA, CTG, TTA, TTG CCT, CCC, CCA, CCG GTT, GTC, GTA, GTG
H
O N
O O O O O
NH2 O
OH O N
OH NH2 OH O OH H2N N OH OH
NH2 H
NH2 NH2
HO
O NH2 NH2 HN NH2
OH
O
PHENYLALANINE F TRYPTOPHAN W TYROSINE Y ASPARTIC ACID D GLUTAMIC ACID E ARGININE R HISTIDINE H

Phe Trp Tyr Asp Glu Arg His
TTT, TTC TGG TAT, TAC GAT, GAC GAA, GAG CGT, CGC, CGA, CGG, AGA, AGG CAT, CAC
O OH O O O O
O O O
H3N S H2N
OH HO OH OH HS OH OH OH H2N OH
NH2 O NH2 NH2
NH2 NH2 NH2
NH2
LYSINE K SERINE S THREONINE T CYSTEINE C METHIONINE M ASPARAGINE N GLUTAMINE Q

Lys Ser Thr Cys Met Asn Gln
AAA, AAG TCT, TCC, TCA, TCG, AGT, AGC ACT, ACC, ACA, ACG TGT, TGC ATG AAT, AAC CAA, CAG
Note: This chart only shows those amino acids for which the human genetic code directly codes for. Selenocysteine is often referred to as the 21st amino acid, but is encoded in a special manner.
In some cases, distinguishing between asparagine/aspartic acid and glutamine/glutamic acid is difficult. In these cases, the codes asx (B) and glx (Z) are respectively used.

BY NC ND
2,4-DINITROPHENYLHYDRAZINE: USES AND RISKS
UK schools have recently been disposing of incorrectly stored 2,4-DNPH. Here we look at what it is and the risks it can pose.
H WHAT IS 2,4-DNPH USED FOR?

H N O O
R1 O N O N
N H
O C O H
C C
H
O
H+
H
C C
H
R2
N C C N – H2O R1 N C C N
H N C C O C N C C O
H
C N R1 & R2 = variable groups H H H
R2
H H
ALDEHYDE/KETONE 2,4-DINITROPHENYLHYDRAZINE A 2,4-DINITROPHENYLHYDRAZONE

C C O
2,4-DNPH can be used to identify aldehydes and ketones. It is commonly used in a mixture of
methanol and sulfuric acid, and reacts with aldehydes and ketones to form an orange-yellow
H C C H
precipitate called a 2,4-dinitrophenylhydrazone. After purification the 2,4-dinitrophenylhydrazone’s
melting point can help identify the specific aldehyde or ketone that was used in the reaction.
C
STORING 2,4-DNPH CORRECTLY AND SAFELY
N FRICTION SENSITIVE PERFECTLY

DRY DAMP SAFE TO OPEN
O O SHOCK SENSITIVE AND USE
2,4-DNPH is supplied damp; It’s recommended that the bottle of damp solid is stored inside a larger
container with a small amount of water at the bottom. If it hasn’t been stored like this, or if there is no
2,4-DINITROPHENYLHYDRAZINE water in the outer container, schools have been told to assume it has dried out, and the bottle should
not be opened due to the risk of a small fire or explosion; in the UK, CLEAPSS should be contacted.

A BASIC GUIDE TO DECODING ORGANIC COMPOUND NAMES
The names of organic molecules can be long and look like a confusing mix of words and numbers. However, they follow a particular set of rules which
allows their structure to be decoded from their name. This graphic summarises some basic rules, and shows how they apply to some organic molecules.
ORGANIC COMPOUND REPRESENTATION FUNCTIONAL GROUPS BOND TYPES
Atoms other than carbon or hydrogen always shown

O O OH
OH NH2
H BUTANE BUT-1-eNE PROP-1-EN-1-OL
O
ALCOHOL ALDEHYDE KETONE AMINE OH
Vertices and line ends are carbon atoms Naming: -ol Naming: -al Naming: -one Naming: -amine
e.g. ethanol e.g. ethanal e.g. propanone e.g. ethanamine BUT-2-eNE BUT-2-YNE PROP-2-EN-1-OL
Organic molecules are usually represented using skeletal formula. In A molecule’s functional group is the group of atoms that give it its Carbon atoms can be linked by single bonds, double bonds, or even
these diagrams, the line ends and vertices represent carbon atoms. chemical properties and reactivity. It’s usually indicated by a suffix triple bonds. The name of the molecule reflects the bonds present.
Hydrogen atoms are ‘implied’ – that is, they are not usually shown, at the end of the name, with a number indicating its position if this -an- present in name – molecule contains only single bonds
but each carbon must have four bonds, and it’s assumed they have is required for clarity. There are many different functional groups. -en- present in name – molecule contains at least 1 double bond
the required number of hydrogens for this to be the case. Atoms -yn- present in name – molecule contains at least 1 triple bond
other than carbon or hydrogen are always shown, and hydrogen Different functional groups have different suffixes. Alcohols (-ol),
atoms are shown if they are bonded to one of these ‘heteroatoms’. aldehydes (-al), & ketones (-one) are examples of functional groups. For double and triple bonds, numbers indicate their position.
PARENT CHAIN SIDE CHAINS STEREOISOMERISM
NUMBER OF CARBONS DENOTED BY PREFIX 2 MAIN TYPES: E-Z ISOMERISM (BELOW)

3 3
1 METH- 6 HEX- & OPTICAL ISOMERISM (RIGHT) C C

4 2 2 4
2-methylbutane 3-methylPENTANE 2,4-DImethylPENTANE 1 1
2 ETH- 7 HEPT-
BUTANE
3 PROP- 8 OCT- S R
OH (E)-BUT-2-ENE (Z)-BUT-2-ENE
E = heavier groups on Z = heavier groups on Groups numbered based on weight of atoms
4 BUT- 9 NON- 4-ETHYLNONAN-1-OL 3,5,7-trimethyldecane
opposite side of double bond same side of double bond they contain, with 4 being the lowest.
5 PENT- 10 DEC- HEXANE Chemical names sometimes contain a letter in brackets; for
Molecules can have one or more carbons that aren’t part of the
example, (Z), (E), (R), or (S). These refer to stereoisomerism: when a
parent chain, referred to as ‘side chains’. The number of carbons in
the side chain is used to name it, in the same way as for the parent molecule has the same chemical formula as another, but a different
Part of the organic molecule’s name denotes how many carbons chain, but the ending -yl is then added. A number is added to show arrangement in 3D space. This can be due to a different arrangement
make up its ‘parent chain’. This is defined as the longest continuously the location of the side chain on the parent chain. If there is more of atoms around a double bond, or when a molecule has two different
connected chain of carbon atoms including the functional group in than one of the same side chain at different points, the prefixes di- arrangements of four different groups of atoms around a central
the molecule. Carbons not included are dealt with as ‘side chains’. (2), tri- (3), or tetra- (4) are used in the name. carbon which are non-superimposable mirror images.

C Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International licence. BY NC ND
AROMATIC FUNCTIONAL GROUP INTERCONVERSIONS
O
OH I F R
S I2 & conc. HNO3, refux

PHENYLSULFONIC ACID IODOBENZENE FLUOROBENZENE N AZOBENZENE
N
O
H2SO 4 cat., H2O, heat
Coupling reaction
H2SO 4, heat under refux
C6H5R, NaOH, <10˚C

KI (aq), room temp.
Br2 & FeBr3 cat., room temperature Br

BROMOBENZENE
HBF4 - flter of solid, dry & heat
N
HBr, CuBr cat., room temperature N
BENZENEDIAZONIUM
OH H2O, 160˚C
Powdered Zn, heat
BENZENE PHENOL
KCN & copper powder

NaOH with Cu salt cat., 200 atm & 350˚C, then HCl Cl HCl, CuCl cat., room temp.
CHLOROBENZENE
CuCN, polar solvent, refux (also for Ar-Br)
Cl2 & AlCl3 cat., room temperature
Na & RI, dry ether

Chloroalkane, AlCl3 cat., room temperature N
0.1M H2SO 4, H2O C
HNO3, H2SO 4 cat., 55˚C BENZONITRILE
KNH2, NH3, -33˚C; then dilute acid

O
SnCl2 (ether), HCl, 20˚C, then boil with H2O

R Cl BENZOYL CHLORIDE
ALKYLBENZENE
REACTIONS KEY
KMnO4, H2SO4, heat
O
SOCl2, heat
SUBSTITUTION CH3 PHENYLKETONE
NO2 H 2O
NITROBENZENE
HCl, refux, Sn; NaOH
OXIDATION
O O
REDUCTION
BENZOIC ACID H BENZALDEHYDE
OH
NH2
HYDROLYSIS PHENYLAMINE
ACYLATION
CO, HCl & AlCl3 cat, CuCl
OTHER
RCOCl, AlCl3 cat., refux 60˚C
Diazotisation: NaNO2 (aq), dilute HCl, temp. 0-5˚C
Cold H3PO2 (aq)

BY NC ND
BENZENE DERIVATIVES IN ORGANIC CHEMISTRY
A WIDE VARIETY OF IMPORTANT ORGANIC COMPOUNDS ARE DERIVED FROM BENZENE, BY REPLACING ONE OF THE HYDROGENS WITH A DIFFERENT FUNCTIONAL GROUP.
THEY CAN HAVE BOTH COMMON & SYSTEMATIC NAMES, WHICH CAN BE CONFUSING; HERE, COMMON NAMES ARE SHOWN PRIMARILY, WITH SYSTEMATIC NAMES SHOWN IN ITALICS.
HALOGEN-CONTAINING HYDROCARBON DERIVATIVES OXYGEN-CONTAINING NITROGEN-CONTAINING SULFUR-CONTAINING POLYAROMATICS
CH3
F Cl Br I CH3
CH3 CH2
CH3
FLUOROBENZENE CHLOROBENZENE BROMOBENZENE IODOBENZENE TOLUENE CUMENE ETHYLBENZENE STYRENE

Fluorobenzene Chlorobenzene Bromobenzene Iodobenzene Methylbenzene Isopropylbenzene Ethylbenzene Vinylbenzene
C6H5F C6H5Cl C6H5Br C6H5I C7H8 C9H12 C8H10 C8 H8
O O O O
CH3 H3C CH3 CH3 OH
CH3
OH H CH3 O
CH3 H3C
ORTHO-XYLENE META-XYLENE PARA-XYLENE PHENOL BENZOIC ACID BENZALDEHYDE ACETOPHENONE METHYL BENZOATE
1,2-dimethylbenzene 1,3-dimethylbenzene 1,4-dimethylbenzene Hydroxybenzene Benzenecarboxylic Acid Benzenecarbaldehyde 1-phenylethanone Methyl Benzoate
C8H10 C8H10 C8H10 C6H5OH C6H5COOH C6H5CHO C6H5COCH3 C8H8O2
O O
O NH2 NO2 N OH
CH3 C S
NH2
O
ANISOLE ANILINE NITROBENZENE BENZoNITRILE BENZAMIDE BENZENESULFONIC ACID NAPHTHALENE ANTHRACENE

Methoxybenzene Aminobenzene Nitrobenzene Benzonitrile Benzamide Benzenesulfonic Acid Naphthalene Anthracene
C6H5OCH3 C6H5NH2 C6H5NO2 C6H5CN C6H5CONH2 C6H5SO3H C10H8 C14H10

BY NC ND
HETEROCYCLES IN ORGANIC CHEMISTRY
A HETEROCYCLE IN ORGANIC CHEMISTRY IS A RING OF CONNECTED ATOMS, WHERE ONE OR MORE OF THE ATOMS IN THE RING ARE ELEMENTS DIFFERENT FROM CARBON.
HETEROCYCLES WITH OXYGEN, NITROGEN, AND SULFUR ARE THE MOST PREVALENT; SELENIUM, BORON, SILICON, ARSENIC & PHOSPHORUS CAN ALSO BE INCORPORATED.
OXYGEN-BASED HETEROCYCLES NITROGEN-BASED HETEROCYCLES SULFUR-BASED HETEROCYCLES MULTIPLE HETEROATOM HETEROCYCLES
O N N
O O O O O
H H
ETHYLENE OXIDE Tetrahydrofuran FURAN TETRAHYDROPYRAN 4H-PYRAN 1,4-DIOXANE ETHYLENe IMINE PYRROLIDINE
Oxirane Oxolane Oxole Oxane 4H-Oxine p-Dioxane Aziridine Azolidine
C 2H4 O C4 H 8 O C4H4O C5H10O C5H6O C4H8O2 C2H5N C4H9N
N N
N
N N
N N N
N N N
H H H H H N N N
PYRROLE IMIDAZOLE PYRAZOLE TRIAZOLE PIPERIDINE PYRIDINE PYRIMIDINE PYRIDAZINE

Azole 1,3-diazole 1,2-diazole 1,2,4-triazole Azinane Azine 1,3-diazine 1,2-diazine
C4H5N C3H4N2 C3H4N2 C2H3N3 C5H11N C5H5N C4H4N2 C4H4N2
N O
N N
S S S S O S N
N H
PYRAZINE ETHYLENE SULFIDE TETRAHYDROTHIOPHENE THIOPHENE TETRAHYDROTHIOPYRAN OXAZOLE THIAZOLE MORPHOLINE

1,4-diazine Thiirane Thiolane Thiole Thiane 1,3-oxazole 1,3-thiazole Tetrahydro-1,4-oxazine
C4H4N2 C2H4S C4H8S C4H4S C5H10S C3H3NO C3H3NS C4H9NO

BY NC ND
ORGANIC FUNCTIONAL GROUP INTERCONVERSIONS
H H R1 O
Cracking (variety of products) R2 O2, Ag cat., 250-300˚C, 10-20 atm (ethene only); other alkenes: RCO3H in CH2Cl2
C C ALKENE R1 C C R2 EPOXIDE
R1 C C R2 ALKANE R3 R4
H2, Ni cat., 150˚C, 5 atm R3 R4
H H
Polymerisation
Hydrogen halide & UV light
Steam, 300˚C, 60 atm, conc. H3PO 4 cat.

ADDITION POLYMER
Conc. H2SO 4
Al2O3, 300˚C, or conc. H2SO 4, refux

Hydrogen halide (aq), room temperature
Hot, conc. KOH, alcoholic solution

O O
H2SO 4, heat (1˚ alcohols only) O ACID ANHYDRIDE
R1 R2 ETHER R1
C
O
C
R2
H H
R1 C C R2 ALKYL HYDROGENSULFATE
H OSO3H
H2O, warm
R X HALOALKANE
O
1˚ only: Cr2O72-, H+, distil
H2O, refux
P2O5, distil
NaOH (aq), refux Cr2O72-, H+, refux
R OH ALCOHOL C ALDEHYDE
KCN, ethanolic solution, refux
NaBH4 (aq, heat) or LiAlH4 (ether)
R H
O
Conc. NH3, heat in sealed tube 2˚ only: Cr2O72-, H+, refux
C KETONE
ROH (anhydrous), refux

NaBH4, alcoholic or alkaline aq. solution, heat; or LiAlH4 in dry ether R1 R2
REACTIONS KEY 1˚ only: Cr2O72-, H+, refux

O
CARBOXYLIC ACID
C
ADDITION NaBH4, alcoholic or alkaline aq. solution, heat; or LiAlH4 in dry ether R OH
H+ (aq), H2O, refux
SUBSTITUTION R C N NITRILE
LiAlH4 (ether)
ROH, conc. H2SO 4 cat.

OXIDATION H2SO 4 & heat
Refux, H+ or OH -
REDUCTION
P2O5, distil
O
H 2O
ELIMINATION H 2O
R NH2 AMINE
C ACYL CHLORIDE
SClO2, PCl3 or PCl5, refux
HYDROLYSIS R Cl
ACYLATION O
O
Conc. NH3, room temp. (gives 1˚ amide) ROH, room temp. C ESTER
ESTERIFICATION LiAlH4 (ether) C AMIDE R1 OR2
RNH2, refux (gives 2˚ amide)
R NH2
OTHER
NH3, refux (gives 1˚ amide); RNH2, refux (gives 2˚ amide)

BY NC ND
FUNCTIONAL GROUPS IN ORGANIC CHEMISTRY
FUNCTIONAL GROUPS ARE GROUPS OF ATOMS IN ORGANIC MOLECULES THAT ARE RESPONSIBLE FOR THE CHARACTERISTIC CHEMICAL REACTIONS OF THOSE MOLECULES.
IN THE GENERAL FORMULAE SHOWN BELOW FOR EACH FUNCTIONAL GROUP, ‘R’ REPRESENTS THE REST OF THE MOLECULE, AND ‘X’ REPRESENTS ANY HALOGEN ATOM.
HYDROCARBONS SIMPLE OXYGEN HETEROATOMICS HALOGEN HETEROATOMICS CARBONYL COMPOUNDS NITROGEN-BASED SULFUR-BASED AROMATIC
H H R1 R2 O
O R1 C C R2
R1 C C R2 C C R1 C C R2 R OH R1 R2 R3 R4
R X
R3 R4
H H
ALKANE ALKeNE ALKyNE ALCOHOL ETHER Epoxide haloalkane

Naming: -ane Naming: -ene Naming: -yne Naming: -ol Naming: -oxy -ane Naming: -ene oxide Naming: halo-
e.g. ethane e.g. ethene e.g. ethyne e.g. ethanol e.g. methoxyethane e.g. ethene oxide e.g. chloroethane
O O O O O O O O
C C C R1
C
O
C
R2
C C C
R H R1 R2 R OH R1 OR2 R NH2 R X
ALDEHYDE KETONE CARBOXYLIC ACID ACID ANHYDRIDE ESTER AMIDE ACYL HALIDE
Naming: -al Naming: -one Naming: -oic acid Naming: -oic anhydride Naming: -yl -oate Naming: -amide Naming: -oyl halide
e.g. ethanal e.g. propanone e.g. ethanoic acid e.g. ethanoic anhydride e.g. ethyl ethanoate e.g. ethanamide e.g. ethanoyl chloride
R3
N N R1
R NH2 R C N C
R C N N R SH R
R1 R2
O R2
AMINE NITRILE IMINE ISOCYANaTE AZO COMPOUND THIOL ARENE

Naming: -amine Naming: -nitrile Naming: -imine Naming: -yl isocyanate Naming: azo- Naming: -thiol Naming: -yl benzene
e.g. ethanamine e.g. ethanenitrile e.g. ethanimine e.g. ethyl isocyanate e.g. azoethane e.g. methanethiol e.g. ethyl benzene

This graphic is shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. BY NC ND
ORGANIC FUNCTIONAL GROUP INTERCONVERSIONS
H H R1 O
Cracking (variety of products) R2 O2, Ag cat., 250-300˚C, 10-20 atm (ethene only); other alkenes: RCO3H in CH2Cl2
C C ALKENE R1 C C R2 EPOXIDE
R1 C C R2 ALKANE R3 R4
H2, Ni cat., 150˚C, 5 atm R3 R4
H H
Polymerisation
Steam, 300˚C, 60 atm, conc. H3PO 4 cat.

ADDITION POLYMER
Conc. H2SO 4
Al2O3, 300˚C, or conc. H2SO 4, refux

Halogen & UV light
Hydrogen halide (aq), room temperature
Hot, conc. KOH, alcoholic solution

O O
H2SO 4, heat (1˚ alcohols only) O ACID ANHYDRIDE
R1 R2 ETHER R1
C
O
C
R2
H H
R1 C C R2 ALKYL HYDROGENSULFATE
H OSO3H
H2O, warm
R X HALOALKANE
O
1˚ only: Cr2O72-, H+, distil
H2O, refux
P2O5, distil
NaOH (aq), refux Cr2O72-, H+, refux
R OH ALCOHOL C ALDEHYDE
KCN, ethanolic solution, refux
NaBH4 (aq, heat) or LiAlH4 (ether)
R H
O
Conc. NH3, heat in sealed tube 2˚ only: Cr2O72-, H+, refux
C KETONE
ROH (anhydrous), refux

NaBH4, alcoholic or alkaline aq. solution, heat; or LiAlH4 in dry ether R1 R2
REACTIONS KEY 1˚ only: Cr2O72-, H+, refux

O
CARBOXYLIC ACID
C
ADDITION LiAlH4 in dry ether R OH
H+ (aq), H2O, refux
SUBSTITUTION R C N NITRILE
LiAlH4 (ether)
ROH, conc. H2SO 4 cat.

OXIDATION H2SO 4 & heat
Refux, H+ or OH -
H2O & acid/base catalyst
REDUCTION
P2O5, distil
O
ELIMINATION H 2O
R NH2 AMINE
C ACYL CHLORIDE
SOCl2, PCl3 or PCl5, refux
HYDROLYSIS R Cl
ACYLATION O
O
Conc. NH3, room temp. (gives 1˚ amide) ROH, room temp. C ESTER
ESTERIFICATION LiAlH4 (ether) C AMIDE R1 OR2
RNH2, refux (gives 2˚ amide)
R NH2
OTHER
NH3, refux (gives 1˚ amide); RNH2, refux (gives 2˚ amide)

BY NC ND
A GUIDE TO OXIDATION REACTIONS OF ALCOHOLS
Compounds containing the alcohol functional group (–OH) can be oxidised to produce carbonyl compounds. Here’s how it happens.
THE REAGENTS THE APPARATUS TESTING FOR REACTION PRODUCTS
H CH3 CH3 DISTILLATION

1˚ alcohol aldehyde
Oxidising agents can be represented simply in chemical
(excess alcohol used)
H3C C OH WATER OUT equations as [O]. An example reaction is shown below.
H3C C OH H3C C OH
H H CH3 O O
WATER IN [O] [O]
PRIMARY (1˚) ALCOHOL SECONDARY (2˚) ALCOHOL TERTIARY (3˚) ALCOHOL
Carbon attached to –OH has one Carbon attached to –OH has two Carbon attached to –OH has three
OH
other carbon directly attached. other carbons directly attached. other carbons directly attached. H OH
Alcohols can be oxidised to carbonyl compounds ETHANOL ETHANAL ETHANOIC ACID

ALCOHOL & ACIDIFIED
(containing a C=O bond) using an oxidising agent. DICHROMATE Note: In step 1, water (H2O) is lost as a side product of the reaction
Acidified dichromate (VI) salts can be used, though due
to their toxicity alternative reagents can also be utilised, DISTILLED PRODUCT 3 C 2H 5OH + 2 Cr2O 72– + 16 H+ 3 CH 3COOH + 4 Cr3+ + 11 H2O
such as pyridinium chlorochromate (PCC). HEAT
DICHROMATE (ORANGE) CHROMIUM ION (GREEN)
An aldehyde can be obtained from

Na2Cr2O7 K 2Cr2O7 primary alcohols using distillation (above). There are two different chemical reactions that can be
Otherwise, heating under reflux (below) used to identify the products of oxidation reactions.
SODIUM DICHROMATE POTASSIUM DICHROMATE is used to make sure the alcohol is fully
oxidised before distilling off the product.
FEHLING’S SOLUTION TOLLEN’S REAGENT
The type of compound obtained from the reaction
HEATING UNDER
depends on the starting alcohol (shown below). When an REFLUX WATER OUT
Contains complexed Cu2+ ions. Contains the diamine silver ion,
oxidation reaction is carried out with a dichromate salt, 1˚ alcohol carboxylic acid
Aldehydes reduce these ions to red [Ag(NH3) 2]+. Aldehydes reduce this
the dichromate ion (Cr2O72–) is reduced to the Cr3+ ion, (excess oxidising agent used) copper (I) oxide. Ketones don’t react to metallic silver, forming a silver
2˚ alcohol ketone with Fehling’s solution. mirror on the glass surface.
giving a colour change from orange to dark green.
WATER IN
DISTIL REFLUX
REACTION PRODUCT WARM
ALDEHYDE WARM
ALDEHYDE
1˚ ALCOHOL ALDEHYDE CARBOXYLIC ACID CONDENSES AND
Blue Red Colourless Silver mirror
DROPS BACK IN TO (or grey silver precipitate)
PEAR-SHAPED FLASK
REFLUX
2˚ ALCOHOL KETONE PRODUCTS ALCOHOL & ACIDIFIED
WITH DIFFERENT DICHROMATE WARM
KETONE WARM
KETONE
DISTIL
ALCOHOLS Solution remains blue; Solution remains colourless;
3˚ ALCOHOL NO REACTION no reaction no reaction
HEAT

A BRIEF GUIDE TO
TYPES OF ORGANIC FORMULAE

A GUIDE TO THE DIFFERENT WAYS ORGANIC COMPOUNDS CAN BE REPRESENTED IN CHEMISTRY
MOLECULAR FORMULA
The molecular formula of an organic compound simply
shows the number of each type of atom present. It tells
C4H8O2
you nothing about the bonding within the compound.
EMPIRICAL FORMULA
The empirical formula of an organic compound gives the
simplest possible whole number ratio of the different
types of atom within the compound.
C2H4O
CONDENSED FORMULA
The condensed formula is also text-based; here, each
carbon atom is listed separately, with atoms attached CH3CH2CH2COOH
to it following. An exception is cyclic parts of molecules,
e.g. benzene, where the carbons are grouped.
DISPLAYED FORMULA H H H O
A displayed formula shows all of the atoms and all of H C C C C

the bonds present in an organic compound. The bonds
are represented as lines. O H
H H H
STRUCTURAL FORMULA O
Similar to displayed formula - not all bonds are shown, H3C CH2 CH2 C
although all atoms are still indicated using subscript
numbers. Carbon hydrogen bonds are often simplified. OH
SKELETAL FORMULA O
In a skeletal formula, most hydrogen atoms are omitted,
and line ends or vertices represent carbons. Functional
groups and atoms other than carbon or hydrogen are
still shown. Easiest to draw & commonly used. OH

A BRIEF GUIDE TO
TYPES OF ISOMERISM IN ORGANIC CHEMISTRY

A GUIDE TO THE FIVE MAIN TYPES OF ISOMERISM THAT CAN BE EXHIBITED BY ORGANIC COMPOUNDS
AN ISOMER OF A MOLECULE IS A MOLECULE WITH THE SAME MOLECULAR FORMULA BUT A DIFFERENT STRUCTURAL OR
SPATIAL ARRANGEMENT OF ATOMS. THIS VARIATION CAN LEAD TO A DIFFERENCE IN PHYSICAL OR CHEMICAL PROPERTIES.
STRUCTURAL ISOMERISM STEREOISOMERISM
CHAIN POSITION FUNCTIONAL GEOMETRIC OPTICAL

H H H H H H H H H H H H CH3 CH3
H Cl
H C C C C H H C C C C H H C C C C H C C
C C
H H H H H H H H Cl H H OH HO H
BUTANE BUT-2-ENE BUT-2-ENE (E)-1,2-DICHLOROETHENE Cl Cl
E = opposite side
H H H L: (S)-1-CHLOROETHANOL
H C H H H H H Cl Cl R: (R)-1-CHLOROETHANOL
H C C H
H H
H C C C C H C C
H C C C H H C C H
H H H H
H H H H H S R
(Z)-1,2-DICHLOROETHENE
METHYL PROPANE BUT-1-ENE CYCLOBUTANE Z = same side
DIFFERENT ARRANGEMENT THE DIFFERING POSITION DIFFERING POSITIONS OF DIFFERENT SUBSTITUENTS NON-SUPERIMPOSABLE
OF A MOLECULE’S CARBON OF THE SAME FUNCTIONAL ATOMS GIVE A DIFFERENT AROUND A BOND WITH MIRROR IMAGES OF THE
SKELETON GROUP IN THE MOLECULE FUNCTIONAL GROUP RESTRICTED ROTATION SAME MOLECULE
The positions of the carbon atoms The molecular formula remains the Also referred to as functional group Commonly exhibited by alkenes, Optical isomers differ by the
in the molecule can be rearranged same; the type of functional group isomerism, these isomers have the presence of two different placement of different substituents,
to give ‘branched’ carbon chains also remains the same, but its the same molecular formula but substituents on both carbon atoms around one or more atoms in a
coming off the main chain. The position in the molecule changes. the atoms are rearranged to give at either end of the double bond molecule. Different arrangements
name of the molecule changes The name of the molecule changes a different functional group. The can give rise to two different, non- of these substituents can be
to reflect this, but the molecular to reflect the new position of the name of the molecule changes to superimposable isomers due to the impossible to superimpose - these
formula is still the same. functional group. reflect the new functional group. restricted rotation of the bond. are optical isomers.

FOR MORE DETAILED INFORMATION ON THE DIFFERENT TYPES OF ISOMERS, GO TO WWW.COMPOUNDCHEM.COM/2014/05/22/TYPESOFISOMERISM
BY NC ND
30TH AUGUST – ERNEST RUTHERFORD’S BIRTHDAY
ERNEST RUTHERFORD
BORN α β +
30 August 1871
Awarded the Nobel Prize in Chemistry for
work on radioactivity, and named alpha
DIED and beta radiation. Also developed the
Rutherford model of the atom from his
19 October 1937 famous gold foil experiment.
Small no. of particles

GOLD FOIL EXPERIMENT show large deflection DETECTING SCREEN
1/8000
In this famous experiment,
α
+ GOLD FOIL
carried out by Hans Geiger and
Ernest Marsden between 1908
and 1913, alpha particles were +
fired at thin metal foils. Most
Most particles show
of the alpha particles passed + little or no deflection
straight through the foil, but a
small number were deflected 7999/8000
back at a large angle. VACUUM
This experiment showed that, contrary to previous models, positive charges (protons) are not spread evenly
throughout the atom, but are concentrated in a small, dense centre: the nucleus. A cloud of negative charges
(electrons) surround this nucleus. Alpha particles that collided with the nucleus were repelled.

BY NC ND
A GUIDE TO DIFFERENT TYPES OF RADIATION
Ionising radiation commonly comes in three different forms: alpha, beta, and gamma radiation. Each of these has a differing
composition, and they also differ in their penetration, ionisation ability, and uses. This graphic summarises each type in turn.
α ALPHA
2 protons & 2 neutrons
ß BETA
High energy electron
γ GAMMA
High energy EM radiation
IONISATION ABILITY: IONISATION ABILITY: IONISATION ABILITY:

HOW PENETRATING? HOW PENETRATING? HOW PENETRATING?
α γ
ALUMINIUM
ALUMINIUM
ALUMINIUM
PAPER
PAPER
ß
PAPER
LEAD
LEAD
LEAD
USES USES USES
Many smoke detectors contain americium-241, which Beta-radiation emitters can be used as tracers in Gamma radiation is used to help sterilise medical
releases alpha radiation and helps detect smoke. medicine to image inside the body, and have also equipment, and can also help sterilise packaged
Alpha radiation-emitting elements have also been been used in cancer treatment. In industry, they have foods. Gamma ray detection is used by a number of
used to power some heart pacemakers and some been used to find leaks in underground pipes, and to telescopes to produce images. They have also been
space probes, including the Mars Curiosity Rover. gauge the thickness of materials during manufacture. used in cancer treatment to help kill cancer cells.

MAKING CHEMICAL REACTIONS HAPPEN FASTER
There are a number of different things that we can change to make a chemical reaction faster. Here, we explain the concept
of collision theory, and how it can be used to explain the effects of five different factors on the rate of a chemical reaction.
COLLISION THEORY INCREASE CONCENTRATION OF REACTANTS INCREASE TEMPERATURE OF REACTION

T1: ROOM TEMPERATURE T 2: ROOM TEMPERATURE + 20˚C
INCREASED INCREASED T1 T1
% OF PARTICLES
% OF PARTICLES
PARTICLES PARTICLES
CONCENTRATION CONCENTRATION WITH ENERGY WITH ENERGY
REQUIRED TO T2 REQUIRED TO
REACT REACT
NO REACTION NO REACTION
ENERGY OF PARTICLES ENERGY OF PARTICLES
CORRECT ORIENTATION
WRONG ORIENTATION INSUFFICIENT ENERGY
SUFFICIENT ENERGY
FREQUENCY OF % SUCCESSFUL FREQUENCY OF % SUCCESSFUL
COLLISIONS COLLISIONS COLLISIONS COLLISIONS
Collision theory states that, for a reaction to occur,
particles must collide with the correct orientation and
with sufficient energy for a reaction to occur. Different Increasing the concentration of reactants in solution Increasing the temperature increases the kinetic
factors affect the rate of the reaction by affecting the increases the rate of reaction as there are a greater energy of particles. This increases the frequency of
frequency of particle collisions, and/or the proportion number of particles available to react. This increases particle collisions, and a greater proportion of collisions
of collisions that have enough energy to react. the frequency of collisions between particles. will have the energy required to react.
INCREASE
PRESSURE
SURFACEOF
AREA
REACTION
OF REACTANTS INCREASE
SURFACEPRESSURE
AREA OF REACTANTS
OF REACTION USE A CATALYST
USE OF A IN
CATALYST
THE REACTION
WITHOUT CATALYST
INCREASED INCREASED INCREASED
SURFACE AREA PRESSURE PRESSURE E a
WITHOUT
CATALYST
ENERGY
WITH CATALYST
E a
WITH
CATALYST
REACTANTS
PRODUCTS
FREQUENCY OF % SUCCESSFUL FREQUENCY OF % SUCCESSFUL Ea = ACTIVATION ENERGY
COLLISIONS COLLISIONS COLLISIONS COLLISIONS
REACTION PROGRESS
Increasing the surface area of solid reactants increases Increasing the pressure of a reaction involving gases A catalyst provides an alternative route for the
the number of particles that are exposed and available forces the gas particles closer together. This will reaction, with a lower activation energy. This means
to react, and as a consequence this increases the increase the frequency of particle collisions, and that particle collisions need less energy in order for a
frequency of particle collisions, increasing rate. therefore increase the rate of reaction. reaction to occur, increasing the rate of the reaction.

HOW DO NUCLEAR REACTORS GENERATE ELECTRICITY?
Nuclear reactors are one way of generating electricity – but how do they work, and what reactions are involved? This graphic takes a look.
THE ANATOMY OF A NUCLEAR REACTOR NUCLEAR FISSION CONTROLLING THE REACTION
94
1 Kr CONTROL RODS
RAISED
CONTROL RODS
LOWERED
235 1 236 36 1
U +n U + 3n ALLOWS MORE SLOWS DOWN
3 6 92 0 92 139 0
REACTIONS TO THE CHAIN
4 Ba
TAKE PLACE REACTION
7 56
5 Control rods, commonly made of boron or

2 144 cadmium, can be lowered into the reactor. They
10 Xe slow the reaction by absorbing neutrons, meaning
235 236
9 1 54 1 there are less available to trigger fission.
PUMP PUMP
U +n U + 2n
0
PUMP 8 92 92 90 0
Sr
38 MODERATORS WATER GRAPHITE
Example uranium fission reactions

1 Containment structure 6 Generator
Moderators help slow neutrons down in the reactor
so that they can be absorbed by uranium atoms.
Uranium oxide pellets are packed into fuel rods
2 Nuclear reactor 7 Transformer to be used as fuel in the reactor. During nuclear
Many nuclear reactors use the water in the reactor
as a moderator, though some use graphite.
fission neutrons collide with uranium-235 atoms
to produce uranium-236, which then splits into
3 Control rods 8 Cool water source
smaller elements, releasing energy. It also releases
more neutrons, leading to a chain reaction, and NUCLEAR WASTE
4 Steam generator 9 Condensor fission of more uranium atoms.
5 Turbine 10 Cooling towers 134
Xe
SPENT FUEL COMPOSITION
239 1 240 54 1
Pu +n Pu + 3n Uranium-238 (95%) Uranium-235 (1%)
In a nuclear reactor, fission reactions generate heat, 94 0 94 103 0
Plutonium (1%) Fission Products (3%)
which heats water and turns it into steam. This steam is then Zr
40
used to drive a turbine which spins a generator, producing
Fission products stay radioactive for many years, and
electricity. The steam used to turn the turbine condenses must be safely stored. Weapons-grade plutonium can
Plutonium-239 is generated by neutron collision
back into water and can be recycled back through the set up be produced in reactors which only expose uranium
with uranium-238, and is also fissionable, creating
to continually drive the turbine. around one third of a nuclear reactor’s energy. to neutron sources for short periods of time.

EQUILIBRIUM AND LE CHÂTELIER’S PRINCIPLE
Reversible chemical reactions reach equilibrium in closed systems (no substances added or lost). Here’s how different conditions affect that equilibrium.
EQUILIBRIUM CONCENTRATION TEMPERATURE PRESSURE
A+B C+D
REACTANT CONCENTRATION INCREASED TEMPERATURE INCREASED ˚C PRESSURE INCREASED Pa
# ˚C Pa
The equilibrium position shifts to The equilibrium position shifts The equilibrium position shifts
reduce the reactant concentration. to reduce the temperature. to reduce the pressure.
In reversible reactions products of the

reaction can react to produce the original
REACTION FORMING THE ENDOTHERMIC REACTION SIDE OF REACTION WITH FEWER
reactants. At dynamic equilibrium the
rates of the forwards and backwards PRODUCTS FAVOURED # WILL BE FAVOURED
ENDO
GAS MOLECULES FAVOURED
reactions are equal; the concentrations of In the example below the new In the example below the new In the example below the new
the reactants and products don’t change. equilibrium mixture will contain a equilibrium mixture will contain equilibrium mixture will contain
higher concentration of C and D. more A and B, and less C and D. more C and D, and less A and B.
REDUCES REACTANT CONCENTRATION EXOTHERMIC DECREASES PRESSURE

1 removes dirt at the same
rate as 2 replaces it. 2 (increases temperature) (fewer gas molecules on right)
1
The size of the hole and
A + 2B C+D A + 2B C+D A + 2B C+D
(decreases temperature) (more gas molecules on left)
pile of dirt stay the same. REDUCES PRODUCT CONCENTRATION ENDOTHERMIC INCREASES PRESSURE
Increasing concentration of one side favours the other. If the forward reaction is exothermic, the backward If the number of gas molecules is the same on either side,
reaction will be endothermic, and vice versa. then changing pressure will have no effect.
LE CHÂTELIER’S PRINCIPLE
PRODUCT CONCENTRATION INCREASED TEMPERATURE DECREASED ˚C PRESSURE DECREASED Pa
An analogy for changing equilibrium conditions
# ˚C
The equilibrium position shifts to The equilibrium position shifts The equilibrium position shifts
reduce the product concentration. to increase the temperature. to increase the pressure. Pa
REACTION FORMING THE EXOTHERMIC REACTION EXO SIDE OF REACTION WITH MORE
Le Châtelier’s principle states that when
REACTANTS FAVOURED # WILL BE FAVOURED GAS MOLECULES FAVOURED
In the example above the new In the example above the new In the example above the new
a change is made to the conditions of a equilibrium mixture will contain a equilibrium mixture will contain equilibrium mixture will contain
dynamic equilibrium, the system moves to higher concentration of A and B. more C and D, and less A and B. more A and B, and less C and D.
counteract the change, causing changes in
quantities of reactants and products.
Note: using a catalyst increases the rate of both the forwards and backwards reactions but doesn’t change the equilibrium position.

WHAT TEMPERATURE DOES WATER BOIL AT?
It might seem a pretty straightforward question – but actually, water’s boiling point can differ at different elevations. This
graphic takes a look at its boiling point in a several different locations, as well as looking at the reasons behind this variance.
EVEREST KILIMANJARO LA PAZ LONDON SEA LEVEL BAKU THE DEAD SEA
ELEVATION: 8848m ELEVATION: 5895m ELEVATION: 3640m ELEVATION: 14m ELEVATION: 0m ELEVATION: –28m ELEVATION: –427m
WATER BOILS: 69.94 ˚C WATER BOILS: 80.33 ˚C WATER BOILS: 87.71 ˚C WATER BOILS: 99.96 ˚C WATER BOILS: 100.0 ˚C WATER BOILS: 100.1 ˚C WATER BOILS: 101.4 ˚C
WORLD’S HIGHEST HIGHEST FREE-STANDING WORLD’S HIGHEST CAPITAL CITY OF THE USED AS RELATIVE WORLD’S LOWEST LOWEST POINT IN
MOUNTAIN MOUNTAIN CAPITAL CITY UNITED KINGDOM ELEVATION REFERENCE CAPITAL CITY THE WORLD
WHY DOES WATER’S BOILING POINT VARY?

KEY
ATMOSPHERIC It’s not so much the elevation that affects water’s boiling point, as
PRESSURE the decreased atmospheric pressure at higher elevations. A liquid
will boil when its vapour pressure is equal to the atmospheric
Decreases with increasing
elevation above sea level. pressure; vapour pressure can be thought of as the tendency of
molecules to escape the liquid’s surface into the gas phase.
WATER WATER MOUNT EVEREST
(AT ROOM TEMP) (AT BOILING TEMP) (LOWER PRESSURE) VAPOUR
PRESSURE Vapour pressure increases with increased temperature, as more
At room temperature, water At sea level, a temperature At a lower surrounding
molecules have the kinetic energy required overcome attractions to
Increases with increasing
doesn’t boil, as the vapour of 100 ˚C is needed for the pressure, the water requires a
water temperature. other water molecules. At lower pressures, molecules escape more
pressure of the water is water’s vapour pressure to lower vapour pressure for it to
lower than the surrounding equal atmospheric pressure, be equal to the surrounding easily, as the vapour pressure required for them to do this is lower.
atmospheric pressure. and for the water to boil. pressure and to boil.

ACIDS, ALKALIS, AND THE pH SCALE
The pH scale is a way of gauging the acidity or alkalinity of a solution. It is calculated using: pH = -log10[H+]. Adding an
acid to water increases the H+ (H3O+) concentration, and decreases the OH- concentration. An alkali does the opposite.
pH H+ CONCENTRATION OH- CONCENTRATION EVERYDAY EXAMPLE

(in moles per litre) (in moles per litre)
14 1 × 10 -14 1 Drain Cleaner

ALKALINE
13 1 × 10 -13 0.1 Bleach

Purple
12 1 × 10 -12 0.01 Ammonia

Blue
11 1 × 10 -11 0.001 Soap
10 1 × 10 -10 1 × 10 -4 Antacid Tablets

Turquoise
9 1 × 10 -9 1 × 10 -5 Baking Soda
8 1 × 10 -8 1 × 10 -6 Seawater
NEUTRAL 7 1 × 10 -7 1 × 10 -7 Pure Water

Green
6 1 × 10 -6 1 × 10 -8 Urine (average)
A C I D I C
5 1 × 10 -5 1 × 10 -9 Black Coffee
Yellow
4 1 × 10 -4 1 × 10 -10 Tomato Juice

Orange
3 0.001 1 × 10 -11 Soda
2 0.01 1 × 10 -12 Lemon Juice

Red
1 0.1 1 × 10 -13 Stomach Acid
0 1 1 × 10 -14 Battery Acid

THE SECRETS OF THE COKE AND MENTOS FOUNTAIN
THE COKE AND MENTOS FOUNTAIN 2-LITRE BOTTLE = 15 grams DISSOLVED CO2
When Mentos are added to a bottle of
Coke their surface acts as a nucleation site,
TURNS INTO 8 LITRES OF CO2 GAS
allowing carbon dioxide bubbles to form
rapidly and causing the fountain effect. It
has been suggested that additives such as
artificial sweeteners increase the fountain’s
height by lowering the surface tension. New
research has suggested other compounds
present may also affect fountain height.
HOW DOES THE TYPE OF CARBONATED BEVERAGE AFFECT THE FOUNTAIN HEIGHT?
3.5 m
3.0m
2.5m
2.0m
1.5m
1.0m
0.5 m
0.0m
Seltzer Caffeine Cherry Diet Diet Coke Diet Coke Diet Cherry Diet Sprite Pepsi
Coke Pepsi Dr. Pepper Sprite
water -free Coke Dr. Pepper Pepsi Coke Zero (caffeine-free) Dr. Pepper Dr. Pepper Zero Max
In each case 11 Mentos candies were introduced to two-litre bottles of commercial carbonated beverages. Generally diet sodas
showed the highest fountains, followed by sugar-sweetened sodas (likely due to increased viscosity), then seltzer water.
THE EFFECT ASPARTAME BENZOATE Experiments with different dissolved

solutes in seltzer water showed that
OF SOLUTES UP TO 3× HEIGHT UP TO 3× HEIGHT different compounds affect fountain
height by varying amounts, and at
CITRAL LINALOOL CITRIC ACID quantities typically found in soft drinks
(with the exception of citric acid, where
UP TO 4× HEIGHT UP TO 4× HEIGHT UP TO 6× HEIGHT more was required to observe an effect).
THE SCIENTIFIC EXPLANATION BUBBLE SIZE

DECREASES
Dissolved solutes in carbonated drinks stop
bubbles combining into bigger bubbles. FOUNTAIN SIZE
With smaller bubbles there is a higher INCREASES
surface area for carbon dioxide to enter the
bubbles, increasing the rate of degassing.
WITHOUT SOLUTE WITH SOLUTE
New demonstrations and new insights on the mechanism of the Candy-Cola soda geyser – T S Kuntzleman, L S Davenport,
V I Cothran, J T Kuntzleman, D J Campbell; J Chem Educ; DOI: 10.1021/acs.jchemed.6b00862

CHEMUNICATE Based on materials provided by Thomas Kuntzleman, Department of Chemistry, Spring Arbor University
POISON CHEMISTRY - CYANIDE COMPOUNDS
Cyanide is a fast-acting, bitter-tasting poison, and one of the deadliest known. Its compounds have famously been utilised in suicide pills over the years.
H I S T O R Y T R E A T M E N T
Cyanide has been used for centuries as a poison, but was HCN KCN NaCN O O
H2NOC
CONH2
SODIUM
THIOSULFATE
first identified in 1782 by the Swedish chemist Scheele; H2NOC
in fact, it’s thought Scheele’s death may have been HYDROGEN POTASSIUM SODIUM N H
N O
R N CONH2
Co+
contributed to by cyanide exposure. CYANIDE CYANIDE CYANIDE AMYL NITRITE H N N
H2NOC O
(Note: KCN and NaCN both get converted to HCN by stomach acid) CONH2
Na+ -O S O- Na+
During WWI, the French attempted to use hydrocyanic + N O
N
acid, then cyanogen chloride, in chemical warfare. In WWII, Na -

O O
NH
HO N S
O O
The Nazis used hydrogen cyanide in the form of Zyklon B O P O
VITAMIN B12a
SODIUM NITRITE O-
to kill millions in their concentration camps. HO
Hydrogen cyanide gas has previously been used for pest (HCN ONLY)
The most prevalent antidotes are nitrites, which convert haemoglobin
control, which sometimes led to accidental deaths. Today, into methemoglobin, which then removes cyanide from cytochrome
cyanides are still used in the mining of gold and silver, and MEDIAN LETHAL DOSE: 3-8mg/kg oxidase. Thiosulfate helps convert cyanide to thiocyanate so it can
in organic synthesis reactions. O R A L - VA R I E S D E P E N D I N G O N F O R M O F C YA N I D E A D M I N I S T E R E D be excreted. Cobalt ions also form a stable complex with cyanide.
E F F E C T S D E T E C T I O N
Sample added to Transferred to solution Adding hydrochloric
5% NaOH solution of 5% FeSO 4 & 1% FeCl3 acid solution gives
prussian blue.
DIZZINESS & NAUSEA & RAPID BREATHING & LOW BLOOD

HEADACHE VOMITING HEART RATE PRESSURE
60˚C
1:6 HCl:H2O
HEAT
LOSS OF RESPIRATORY CONVULSIONS
CONSCIOUSNESS FAILURE & DEATH 1 MIN 10 MINS 10-15 MINS
Cyanide inhibits the cytochrome oxidase enzyme, preventing the A common test for cyanide in the early 20th Century formed prussian
body’s cells from using oxygen. HCN smells of bitter almonds, but blue, an iron-cyanide complex, in the presence of cyanide ions.
only ~40% of people have the genetic ability to smell it. Many fruit There are several other chemical tests, including portable card-
seeds also contain small amounts of cyanide-containing compounds. based tests, and instrumental methods can also be used.

POISON CHEMISTRY - THALLIUM SULFATE
Sometimes referred to as ‘the poisoner’s poison’, thallium sulfate is colourless, odourless, and tasteless. It is slow-acting, and diicult to diagnose.
Thallium was discovered in 1861 by William Crookes, and
its toxicity was quickly noted. It is especially toxic in its
bivalent compounds, including thallium sulfate, acetate,
Tl 2 SO 4 Fe7(CN)18
PRUSSIAN BLUE
O
SH
and carbonate. OH
N
In the late 1800s, thallium sulfate was used to treat some
medical conditions, including syphilis, gonorrhoea, &
THALLIUM (I) SULFATE NaI
H
O
gout. The side efects meant that it was not widely used,
SODIUM IODIDE N-ACETYLCYSTEINE
however.
Thallium sulfate was often employed as a rodenticide
No substance can remove thallium which has already been absorbed,
and insecticide, making it easy for would-be poisoners to
but Prussian blue and sodium iodide help remove unabsorbed
obtain. Its usage in rat poisons has been banned in many
thallium from the intestinal tract. As thallium binds to sulfhydryl
countries since the 1970s, however.
MEDIAN LETHAL DOSE: 10-15mg/kg groups, N-acetylcysteine has also been suggested as a treatment.
0.4% BISMUTH NITRATE

IN 20% NITRIC ACID, THEN
10% SODIUM IODIDE IN
A SATURATED SODIUM
CONSTIPATION ABDOMINAL VOMITING & PAIN IN THIOSULFATE SOLUTION
PAIN NAUSEA EXTREMITIES
‘MEES’ LINES’ HAIR LOSS INCREASED CONVULSIONS,

ON NAILS HEART RATE COMA & DEATH URINE RED PRECIPITATE OF
THALLIUM BISMUTH IODIDE
Initial symptoms indistinct. Large doses kill before some efects Qualitative testing for thallium in urine can be carried out as detailed
are apparent, but with lower doses, hair loss occurs 2-3 weeks after above, though this method can produce false positive results. More
poisoning. Damage to nerves, causing pain, is also characteristic. common is the use of atomic absorption photospectrometry of a
Toxicity is due to the similarity between potassium & thallium ions. urine sample, which uses absorption of light to identify thallium.

POISON CHEMISTRY - WHITE ARSENIC
Arsenic is a notorious poison; colourless, odourless white arsenic was a popular choice for poisoners, and was commonly known as ‘The King of Poisons’.
White arsenic has been known for centuries. In Ancient
Rome, Nero’s supposed use of it to poison his brother &
become emperor is one of the first documented cases.
As 2 O 3 HS O SH
OH
HO
In the 17th & 18th centuries, white arsenic’s use as a poison ARSENIC (III) OXIDE OH
was widespread, and earned it the nickname ‘inheritance HS SH O
powder’. However, its usage as a poison rapidly declined
after the development of chemical tests. DIMERCAPROL DIMERCAPTOSUCCINIC ACID
Around 50,000 tonnes of arsenic trioxide are still produced Chelating agents, such as the above compounds, bind the arsenic
annually, and used as a precursor to a range of compounds. ions and prevent them from inhibiting enzymes. However, chelation
It’s also been used as a treatment for some leukaemias. therapy itself can have side effects. Dimercaprol has been largely
MEDIAN LETHAL DOSE: 15.1mg/kg superseded by 2,3-dimercapto-1-propanesulfonic acid.
HEADACHE DISCOLOURATION VOMITING & BREATH SMELLS SILVER-BLACK

OF NAILS METALLIC TASTE OF GARLIC
RESIDUE FORMS
HEAT
STOMACH PAIN & HAIR LOSS CONVULSIONS CONVULSIONS,
DIARRHOEA COMA & DEATH SAMPLE, ZINC, & SULFURIC ACID
Symptoms usually appear around 30 minutes after ingestion. Arsenic The Marsh Test involves reaction of a sample with zinc and acid.
interferes with cell enzymes, respiration and mitosis. The skin, lungs, If arsenic is present, it is converted to arsine gas. Heating arsine
kidneys and liver are the major organs affected, with death occuring decomposes it; a silver-black deposit of arsenic is formed on cooling.
either from circulatory inefficiency, or liver or kidney failure. Modern spectroscopic methods are now used instead of this test.

FUGU & TETRODOTOXIN
O MAIN LOCATIONS
OH
O
O OH H NH2
N liver
HO N
HO H
OH skin
TETRODOTOXIN sex organs
Tetrodotoxin is produced by bacteria that live in pufferfish. The parts of the

fish which contain high levels of the toxin must be skillfully removed before
eating. Tetrodotoxin is heat stable so can’t be broken down by cooking.
O
OH
O
O OH H NH2
N
HO N
OH
HO H blocks nervous causes loss of sensation, paralysis,
system messages respiratory arrest, and death.
The estimated median lethal dose of tetrodotoxin is 0.33 milligrams per

kilogram of body weight. There is no known antidote for the toxin.

POISON CHEMISTRY - CYANIDE COMPOUNDS
Cyanide is a fast-acting, bitter-tasting poison, and one of the deadliest known. Its compounds have famously been utilised in suicide pills over the years.
Cyanide has been used for centuries as a poison, but was HCN KCN NaCN O O
H2NOC
CONH2
SODIUM
THIOSULFATE
first identified in 1782 by the Swedish chemist Scheele; H2NOC
in fact, it’s thought Scheele’s death may have been HYDROGEN POTASSIUM SODIUM N H
N O
R N CONH2
Co+
contributed to by cyanide exposure. CYANIDE CYANIDE CYANIDE AMYL NITRITE H N N
H2NOC O
(Note: KCN and NaCN both get converted to HCN by stomach acid) CONH2
Na+ -O S O- Na+
During WWI, the French attempted to use hydrocyanic + N O
N
acid, then cyanogen chloride, in chemical warfare. In WWII, Na -

O O
NH
HO N S
O O
The Nazis used hydrogen cyanide in the form of Zyklon B O P O
VITAMIN B12a
SODIUM NITRITE O-
to kill millions in their concentration camps. HO
Hydrogen cyanide gas has previously been used for pest (HCN ONLY)
The most prevalent antidotes are nitrites, which convert haemoglobin
control, which sometimes led to accidental deaths. Today, into methemoglobin, which then removes cyanide from cytochrome
cyanides are still used in the mining of gold and silver, and MEDIAN LETHAL DOSE: 3-8mg/kg oxidase. Thiosulfate helps convert cyanide to thiocyanate so it can
in organic synthesis reactions. O R A L - VA R I E S D E P E N D I N G O N F O R M O F C YA N I D E A D M I N I S T E R E D be excreted. Cobalt ions also form a stable complex with cyanide.
Sample added to Transferred to solution Adding hydrochloric
5% NaOH solution of 5% FeSO 4 & 1% FeCl3 acid solution gives
prussian blue.
DIZZINESS & NAUSEA & RAPID BREATHING & LOW BLOOD

HEADACHE VOMITING HEART RATE PRESSURE
60˚C
1:6 HCl:H2O
HEAT
LOSS OF RESPIRATORY CONVULSIONS
CONSCIOUSNESS FAILURE & DEATH 1 MIN 10 MINS 10-15 MINS
Cyanide inhibits the cytochrome oxidase enzyme, preventing the A common test for cyanide in the early 20th Century formed prussian
body’s cells from using oxygen. HCN smells of bitter almonds, but blue, an iron-cyanide complex, in the presence of cyanide ions.
only ~40% of people have the genetic ability to smell it. Many fruit There are several other chemical tests, including portable card-
seeds also contain small amounts of cyanide-containing compounds. based tests, and instrumental methods can also be used.

POISON CHEMISTRY - THALLIUM SULFATE
Sometimes referred to as ‘the poisoner’s poison’, thallium sulfate is colourless, odourless, and tasteless. It is slow-acting, and diicult to diagnose.
Thallium was discovered in 1861 by William Crookes, and
its toxicity was quickly noted. It is especially toxic in its
bivalent compounds, including thallium sulfate, acetate,
Tl 2 SO 4 Fe7(CN)18
PRUSSIAN BLUE
O
SH
and carbonate. OH
N
In the late 1800s, thallium sulfate was used to treat some
medical conditions, including syphilis, gonorrhoea, &
THALLIUM (I) SULFATE NaI
H
O
gout. The side efects meant that it was not widely used,
SODIUM IODIDE N-ACETYLCYSTEINE
however.
Thallium sulfate was often employed as a rodenticide
No substance can remove thallium which has already been absorbed,
and insecticide, making it easy for would-be poisoners to
but Prussian blue and sodium iodide help remove unabsorbed
obtain. Its usage in rat poisons has been banned in many
thallium from the intestinal tract. As thallium binds to sulfhydryl
countries since the 1970s, however.
MEDIAN LETHAL DOSE: 10-15mg/kg groups, N-acetylcysteine has also been suggested as a treatment.
0.4% BISMUTH NITRATE

IN 20% NITRIC ACID, THEN
10% SODIUM IODIDE IN
A SATURATED SODIUM
CONSTIPATION ABDOMINAL VOMITING & PAIN IN THIOSULFATE SOLUTION
PAIN NAUSEA EXTREMITIES
‘MEES’ LINES’ HAIR LOSS INCREASED CONVULSIONS,

ON NAILS HEART RATE COMA & DEATH URINE RED PRECIPITATE OF
THALLIUM BISMUTH IODIDE
Initial symptoms indistinct. Large doses kill before some efects Qualitative testing for thallium in urine can be carried out as detailed
are apparent, but with lower doses, hair loss occurs 2-3 weeks after above, though this method can produce false positive results. More
poisoning. Damage to nerves, causing pain, is also characteristic. common is the use of atomic absorption photospectrometry of a
Toxicity is due to the similarity between potassium & thallium ions. urine sample, which uses absorption of light to identify thallium.

POISON CHEMISTRY - WHITE ARSENIC
Arsenic is a notorious poison; colourless, odourless white arsenic was a popular choice for poisoners, and was commonly known as ‘The King of Poisons’.
White arsenic has been known for centuries. In Ancient
Rome, Nero’s supposed use of it to poison his brother &
become emperor is one of the first documented cases.
As 2 O 3 HS O SH
OH
HO
In the 17th & 18th centuries, white arsenic’s use as a poison ARSENIC (III) OXIDE OH
was widespread, and earned it the nickname ‘inheritance HS SH O
powder’. However, its usage as a poison rapidly declined
after the development of chemical tests. DIMERCAPROL DIMERCAPTOSUCCINIC ACID
Around 50,000 tonnes of arsenic trioxide are still produced Chelating agents, such as the above compounds, bind the arsenic
annually, and used as a precursor to a range of compounds. ions and prevent them from inhibiting enzymes. However, chelation
It’s also been used as a treatment for some leukaemias. therapy itself can have side effects. Dimercaprol has been largely
MEDIAN LETHAL DOSE: 15.1mg/kg superseded by 2,3-dimercapto-1-propanesulfonic acid.
HEADACHE DISCOLOURATION VOMITING & BREATH SMELLS SILVER-BLACK

OF NAILS METALLIC TASTE OF GARLIC
RESIDUE FORMS
HEAT
STOMACH PAIN & HAIR LOSS CONVULSIONS CONVULSIONS,
DIARRHOEA COMA & DEATH SAMPLE, ZINC, & SULFURIC ACID
Symptoms usually appear around 30 minutes after ingestion. Arsenic The Marsh Test involves reaction of a sample with zinc and acid.
interferes with cell enzymes, respiration and mitosis. The skin, lungs, If arsenic is present, it is converted to arsine gas. Heating arsine
kidneys and liver are the major organs affected, with death occuring decomposes it; a silver-black deposit of arsenic is formed on cooling.
either from circulatory inefficiency, or liver or kidney failure. Modern spectroscopic methods are now used instead of this test.

FUGU & TETRODOTOXIN
O MAIN LOCATIONS
OH
O
O OH H NH2
N liver
HO N
HO H
OH skin
TETRODOTOXIN sex organs
Tetrodotoxin is produced by bacteria that live in pufferfish. The parts of the

fish which contain high levels of the toxin must be skillfully removed before
eating. Tetrodotoxin is heat stable so can’t be broken down by cooking.
O
OH
O
O OH H NH2
N
HO N
OH
HO H blocks nervous causes loss of sensation, paralysis,
system messages respiratory arrest, and death.
The estimated median lethal dose of tetrodotoxin is 0.33 milligrams per

kilogram of body weight. There is no known antidote for the toxin.


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SC IENCE & TECHNOLOGY

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