Chemnotes Mod 7

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Module 7 Chemistry Notes
Chemistry- Unit 4 (High School - Australia)
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MODULE 7: Organic Chemistry

Nomenclature
Inquiry Question: How do we systematically name organic chemical
compounds?
Homologous Series
Organic compounds with the same functional groups form part of a homologous series.
Organic compounds are classified into a variety of homologous series depending on the
arrangement of the carbon skeleton, and the groups attached.
Homologous Series Main Features
Alkanes Hydrocarbon chains containing only single bonds (C - C)
Alkenes Hydrocarbon chains containing a carbon-carbon double bond

(C=C)
Alkynes Hydrocarbon chains containing a carbon-carbon triple bond

(C≡C)
Alcohols Contain a hydroxyl (-OH) functional group
Aldehydes and Ketones Contain carbonyl group (C=O)
Carboxylic acids Contain a carboxylic acid functional group (-COOH)
Amines and Amides Contain Nitrogen (N) atom in the chain
Halogenated organic compounds Contain a halogen (Group 7 element) side group such as
fluorine (-F), chlorine (-Cl), bromine (-Br) and iodine (-I)

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Naming Organic Compounds
Prefix + Parent + Suffix
1. Parent:
Number of carbons atoms in the longest continuous chain in the molecule
2. Suffix:
Identifies functional groups that the molecule possesses
3. Prefix:
Each prefix identifies a side group attached to the main carbon chain, and specifies the
location in the chain (numerically). If there are multiples of a particular side group, then
we write di, tri, tetra etc.
No. of Carbons Parent Names
1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
7 Hept-
8 Oct-
9 Non-
10 Dec-

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Primary, Secondary and Tertiary

● Primary carbons are carbons attached to one other carbon.
● Secondary carbons are attached to two other carbons.
● Tertiary carbons are attached to three other carbons.

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Isomers
Molecules that have the same molecular formula but different molecular geometries are
called isomers.
● Chain Isomers
Chain isomers are made up of two or more
carbon or other compounds with the same
molecular formula but different atomic
arrangements, or branches.
● 1,1,1,2,3,5,9,18
● No. of chain isomers from C1 to C8
● Position Isomers
Positional isomers are constitutional isomers that have the same carbon skeleton and
the same functional groups but different location of the functional groups on or in the
carbon chain.
● Functional Group Isomers

Functional Group Isomers have the same molecular formula, but different functional
groups.
● cyclohexane and 1-hexene
Butan-2-one
3-buten-2-ol

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Hydrocarbons
Inquiry question: How can hydrocarbons be classified based on their structure
and reactivity?
Alkanes (C - C)
Alkenes (C = C) Alkynes (C ≅ C)

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Alkyl Side Groups
When Naming:
● Identify and name any side groups
● Side groups are written alphabetically in the compound name, e.g. 1-ethyl-2-methyl…
● Number the main chain carbon atoms consecutively, such that the side groups have the
lowest set of ordinates
● A dash is used to separate numbers and letters, a comma is used to separate numbers
conduct an investigation to compare the properties of organic chemical compounds within a

homologous series, and explain these differences in terms of bonding
Shape of Molecules Formed Between Carbon Atoms
The nature of bonding around each carbon

atom of an organic compound influences the
geometrical shape of that part of the
molecule (VSEPR).
The molecular arrangement can influence

how close these molecules are able to
compact together.

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Physical Properties of Hydrocarbons
Hydrocarbons are nonpolar covalent molecular substances as carbon and hydrogen have
similar electronegativity, and most hydrocarbon molecules have symmetrical sharing of
electrons.
Physical Properties of Alkanes
● The only type of intermolecular force

in alkanes are dispersion forces. So
alkanes generally have low B.P and
M.P.
● At room temperature- C1 to C4 are

gases, C5 to C10 are liquid and C>10
are typically solid. Colourless.
● Insoluble in water and Dissolve

nonpolar substances (The weak dispersion forces between water molecules and
hydrocarbon molecules are not strong enough to overcome the strong attraction between
water molecules)
● Poor conductors of electricity (No free mobile charge carriers, no free electrons)
● Less dense than water (Dispersion forces hold molecules together more loosely than
H-bonds)
● The strength of the overall dispersion forces between molecules increases as the
molecular weight increases. (More electrons lead to a greater amount of temporary
dipole interactions).
○ Therefore, larger alkane = higher B.P and M.P
● The shape of the hydrocarbon also influences B.P and M.P

○ Linear molecules pack closer together allowing for a greater effect with the dispersion
forces between the molecules.
○ Bulkier molecules (molecules with side chains) do not always pack together neatly, so
less overall dispersion forces form.

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○ Melting point versus carbon chain length has more of a step-like curve due to chains
with even numbers of carbon atoms packing slightly more efficiently in the solid
state than chains with odd numbers. The more efficient packing requires more energy
to melt the compound.
Physical Properties of Alkenes and Alkynes
● Similar to their corresponding alkanes (same number of carbon atoms).
● The location of the double and triple bonds influences the molecule geometry and
hence also influences the physical properties.
○ The location of the double or triple bond changes the molecule’s ability to compact
together, changing the effectiveness of the dispersion forces between the molecules.
○ Symmetrical structures allow for closer compaction between the molecules, and greater
effectiveness of the dispersion forces between the molecules, leading to higher B.P and
M.P.
○ Bulky structures do the opposite.
Cyclic Hydrocarbons (Cyclo...)

A hydrocarbon that contains carbon atoms joined together in a ring is called a cyclic
hydrocarbon. They may contain single, double, or triple bonds in the primary chain.
● Non-polar and share similar

properties to their
corresponding open-chain
hydrocarbons
● Less flexible than corresponding
open-chain hydrocarbon since the
single bonded carbons cannot
freely rotate
● Side groups are named similarly to
open-chain hydrocarbon

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● Aromatic hydrocarbons contain one or

more benzene rings
○ The electrons in the benzene ring
are delocalised in that they can
move around the structure
○ The cyclic delocalisation makes it
extremely stable and reactions
involving benzene will often
maintain the ring structure
Naming Halogenated Organic Compounds

Br: bromo- Cl: chloro- F: fluoro- I: iodo-
● If there are more than one of any halogen, then prefixes di-, tri- etc are placed in front of
the halogen name
● Alphabetical order
○ bromo>chloro>fluoro>iodo

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● In haloalkanes, number the main-chain carbon atoms consecutively, such that the side
groups have the lowest set of ordinates.
○ [1,1,1,2,2]
○ NOT [1,1,2,2,2]
● In haloalkenes and haloalkynes, the multiple bond takes priority

○ The carbon atoms are named according to the longest chain containing the
multiple bond, numbered such that the multiple bond has the lowest possible
number
Safety When Handling and Disposing Organic Substances

● Companies and labs which work with organic compounds must use Material Safety Data
Sheets (MSDS)
○ MSDS provide specific details on the hazards, harm minimisation, and safest storing and
handling practices for the compound of interest
○ MSDS must be checked prior to handling
● Many organic compounds are volatile due to weak intermolecular forces and hence can
often form vapours at room temperature
○ The vapours of organic compounds are often colourless and cannot be seen
○ Most have an odour but it is not safe to detect a compound this way
○ Exposure to vapours is minimised by handling all organic compounds in a fume
cupboard OR in an isolated chemical containment system
Toxicity
● Acute/Short-Term Health Effects
○ Headaches
○ Dizziness
○ Slowed Reaction Time
○ Loss of Consciousness
● Chronic/Long-Term Health Effects

○ Chronic Fatigue
○ Liver and Kidney Damage
○ Damage to central nervous system
○ Immune system disorders

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Flammability
Most organic compounds are highly flammable, especially in vapour form.
● Flashpoint - The lowest temperature at which a liquid will ignite

○ The lower the flashpoint, the easier it is to ignite
○ Any organic substance with a flashpoint below 23°C is considered highly flammable
■ Cyclohexane
■ Cyclohexene
■ Ethanol
■ Pentane
● Conduct experiments with organic compounds in well-ventilated rooms where there

are no naked flames.
Disposal of Organic Compounds
● Organic compounds for disposal are collected and stored in specific labelled
containers which are taken by the appropriate disposal companies
● Organic compounds cannot be disposed of in regular drain systems as they can re-enter
the environment and have detrimental effects
○ E.g. They may end up in the ocean as an oil layer, which is disastrous for aquatic
life and birds
Environmental, Economic and Sociocultural Implications of

Obtaining and Using Hydrocarbons from the Earth
The most significant reaction that hydrocarbons undergo is combustion.
● The first fuel sources to be exploited were wood and peat

○ These were used for cooking, baking, smelting and warmth
○ Burning fuel also provided energy for making new materials
● During the Industrial Revolution, coal (a hydrocarbon fuel) began to replace wood as the
main source of energy in Europe and North America
○ Oil and coal gas were later used
○ Then in the 1960s, natural gas (composed of primarily methane but also consists of
ethane, propane, butane, and pentane) began to replace coal gas

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○ These all had a higher energy density than wood

○ These hydrocarbons were called fossil fuels
● In the past 250 years, the use of hydrocarbons for fuel has increased by nearly 800 fold,
the consequences of this include:
Effects
Environmental Economic Societal
Global warming, acid rain, Loss of income in the area of From air pollution: Headaches,
smog, ozone depletion spills dizziness and nausea. Long-term
Large cost of clean-up of spills effects include heart disease,
Destruction of natural lung cancer, and respiratory
ecosystems Job creation diseases.
Contamination of groundwater Increased economic output Mental impact of losses
systems which feed rivers etc. Increases availability of
products and services
● Greenhouse effect - the trapping of the sun's warmth in a planet's lower atmosphere
which is caused by the atmospheric gases that trap infrared radiation
○ Combustion of hydrocarbons releases greenhouse gases into the atmosphere
○ Main greenhouse gases include:
■ Carbon dioxide, methane, nitrous oxide, hydrofluorocarbons, perfluorocarbons
and sulphur hexafluoride.
Fractional Distillation of Petroleum (Crude Oil)
● Petroleum is a complex mixture of

hydrocarbons with a vast range of
hydrocarbon chain lengths
● The mixture is separated into fractions and
then further refined before it can be used
● The crude oil mixture is separated based on
differences in B.P using a fractionating
column
1. Petroleum mixture is heated to a high

temperature of approximately 400°C,
vaporising a large portion of the mixture

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2. Temperature decreased in the tower with increasing height, allowing the heated vapours
to cool.
3. At different stages, hydrocarbons condense out of the mixture, separating the mixture into
fractions
● Short chain molecules condense toward the top of the column

○ Short chain molecules have weak intermolecular forces = low M.P and temperatures
decreases as we increase in height
● Long chain molecules condense toward the bottom of the column
○ Long chain molecules have stronger intermolecular forces = high M.P and temperatures
are higher towards the bottom of the column
● These fractions are the raw materials that become the building blocks of polymers,
pharmaceuticals, industrial solvents, and sources of fuel and energy powering electricity,
industry, vehicles etc.
Fraction Name Use
Gas Used in LPG for cooking and heating.

Also used in some automobiles.
Ethers Solvents in industrial reactions.

Used to create plastics.
Petrol Car fuel, Jet Fuel.
Light Oils Heating Oils
Lubricating Oils Motor oils and used in cooking (fats), lubricants.
Products of Reactions Involving

Hydrocarbons
Inquiry Question: What are the products of reactions of hydrocarbons and how
do they react?
Chemical properties are influenced by the functional groups of the organic compound

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(the reactive parts of the molecule, the double and triple bonds, or side groups which contain
oxygen or nitrogen)
Reactions of Saturated Hydrocarbons

● Chemical reactions occur when the chemical bonds change.
● Alkanes are saturated hydrocarbons as they have only single-bonds
● As they are non-polar, and the (C-C) and (C-H) bonds are relatively strong, alkanes are
relatively inert compared to other homologous series
Combustion of Alkanes
● Alkanes are commonly used as fuels in combustion reactions

● Volatility (the tendency to change from liquid to gas) decreases as the length of the
carbon chain increases, so short-chain molecules such as butane and octane are used
● Alkanes, particularly gaseous and liquid alkanes, are highly flammable
● Complete combustion - excess oxygen - produces CO2 and H2O
● Incomplete combustion - limited oxygen - produces C or CO or CO2 and H2O
Halogenation of Alkanes (Substitution Reactions)
● Alkanes can react with halogens via substitution reactions in the presence of UV light
● One atom is swapped with another
● Useful in the industry as it allows chemists to change a compound into something more
useful

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DON’T FORGET THE STATES

Reactions of Unsaturated Hydrocarbons
Unsaturated hydrocarbons (alkenes and alkynes) are typically more reactive than saturated
hydrocarbons (alkanes) due to their double or triple bond which can be ‘cracked open’ in an
addition reaction.
● Alkenes undergo addition reactions readily and do not require the input of UV light
Halogenation of Alkenes (X2)
● The addition of elemental halogens such as chlorine (Cl2) or Bromine (Br2) results in a
dihalogenated alkane

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Distinguishing Between an Alkane and an Alkene
● Alkanes and corresponding alkenes possess very similar physical properties

● Mixing bromine water with samples of alkane and alkene can distinguish the two
○ Bromine water is an orange-brown mixture of Br2(aq) and HOBr(aq)
(hypobromous acid)
● A reaction between the hydrocarbon and bromine water will decolourise the solution
● Alkanes require UV light in order to react with bromine water, whereas alkenes will
readily react with bromine water
○ So they can be distinguished by the time it takes for the bromine water to be
decolourised
○ E.g Cyclohexane and Cyclohexene can be distinguished with the bromine water
test, they are both colourless and volatile liquids at SLC
○ Risks and Minimisation
■ Organic compounds are volatile and flammable - conduct in a fume
cupboard and in a well ventilated lab
■ Can cause severe irritation to upper respiratory tract upon inhalation, if
ingested can result in severe digestive tract damage, if exposed over a long
term may result in chronic liver and kidney damage
■ Wear protective clothing, gloves, and goggles, handle bromine water with
care (be more specific in exams depending on equipment), thoroughly
wash hands after to remove all remnants of bromine water
Hydrogenation of Alkenes (H2)

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● In the presence of a nickel catalyst and at a temperature of 150°C, ethene will undergo
an addition reaction with H2 gas to produce saturated alkane ethane
○ This type of reaction is used in the food industry to convert unsaturated fats and
oils to margarine
○ Removing the (C=C) bonds increase the melting points, allowing for the
substance to be solid at standard temperature
Hydrohalogenation of Alkenes (HX)
● The addition of a hydrogen halide (HX), to an alkene results in a single

mono-halogenated alkane
● Markovnikov’s rule is applied (the rich get richer) explained below
Markovnikov’s Rule (The Rich Get Richer)
● In the reaction between an alkene and HX, the H will attach to the carbon with fewer
alkyl groups and the X will attach to the carbon with more alkyl group
● The Rich (the carbon with more alkyl groups) Get Richer (by gaining the halogen)
● If the number of alkyl side groups are equal, there are multiple equally-likely
products possible

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● The stability of the carbocation increases with the no. of alkyl side groups attached, so a
tertiary carbocation is more stable than a primary one (might not need to know this)
● The major product is the preferred product based on Markovnikov’s Rule
Hydration of Alkenes (H2O)
● Ethanol can be produced by reacting steam with ethene in the presence of a catalyst,
phosphoric acid, at 300°C and a pressure of 6-7 MPa
● Dilute sulphuric acid can also be used

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Alcohols
Inquiry Question: How can alcohols be produced and what are their properties?
Primary, Secondary and Tertiary Alcohols

● The position of the hydroxyl group classifies the alcohol as primary, secondary or tertiary
● If the hydroxyl (-OH) group is bonded to a carbon that is bonded to 1 other carbon it is a
primary alcohol
○ If the carbon is bonded to 2 other carbons, it is a secondary alcohol
○ If the carbon is bonded to 3 other carbons, it is a tertiary alcohol
● When naming alcohols, and numbering the chain, the location of the hydroxyl group
takes priority over alkyl groups and halogens, but not double or triple bonds
● Alkanol - hydroxyl group is bonded to an alkane
Physical Properties of Alcohols

● The most important physical property of alcohols is the polarity of their hydroxyl
groups
● (C-O) and (O-H) bonds are polar

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● Alcohols can have non-polar and polar parts of the molecule, the (-OH) group allows
the formation of H-Bonds
○ Because of this, compounds such as ethanol can interact with both non-polar and polar
molecules
● As molar mass increases, the physical properties of

alcohols become more like those of hydrocarbons of
similar molar mass
○ This is because, as molar mass increases, the
non-polar part of the alcohol begins to
dominate the nature of the molecule and the
effect of the hydroxyl group is lessened
● Alcohols have higher B.P than alkanes of similar

molar mass
○ H-Bonds, more energy required to overcome these strong intermolecular forces between
alcohol molecules
○ Additional (-OH) groups further increase the extent of H-Bonds, leading to an even
higher B.P
● The extent to which the (-OH) group will participate in H-Bonds depends on how
exposed the (-OH) group is
○ Primary (-OH) groups are more free to participate in H-Bonds with surrounding
molecules as they don’t have local methyl groups
○ Secondary (-OH) groups are less exposed than primary (-OH) groups
○ Tertiary (-OH) groups are the least exposed and their abilities to participate in H-Bonds is
hindered the most
○ Therefore, the more exposed the (-OH) groups, the higher the B.P
● An exception:
○ Some primary alcohols may have lower B.P than their secondary and tertiary isomers
○ This can occur if it has a methyl side group that causes the molecule to not be able to
compact as closely, lessening the impact of its intermolecular forces, decreasing the B.P

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● Alcohols have increased solubility in water compared to alkanes of similar molar mass
○ This is due to how the (-OH) groups can form H-Bonds with water molecules
○ Smaller alcohols such as methanol, ethanol and propan-1-ol are completely soluble in
water whereas alcohols with greater molar mass are much less soluble in water
■ This is because as molar mass increases, the non-polar part of the alcohol begins to
dominate the nature of the molecule and the effect of the hydroxyl group is lessened
■ Therefore less H-Bonds and decreased
solubility
● Ethanol is a universal solvent due to

○ Non-polar and polar parts can interact with
non-polar and polar substances
○ The non-polar chain is not so large that it
dominates the nature of the molecule,
allowing both parts to contribute
significantly
Practical Investigation of Enthalpies of Combustion of

Alcohols
● The heat of combustion of a fuel can be measured using a spirit burner calorimeter

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1. Using q=mCΔT find how much heat the water absorbed

2. Calculate the moles of the fuel combusted
○ Mass of fuel = Mass of spirit burner (Initial) - Mass of spirit burner (Final)
○ n of fuel = mass of fuel / MM of fuel
3. Using ΔHc = -q/n, find heat released by fuel in Jmol/L, then convert to kJmol/L
Causes of Variations to Theoretical Enthalpy of Combustion
● Energy loss to surroundings

● Heat absorbed by the copper can
● Experiment not conducted in SLC
● (Be more specific in exams when stating the effects of the above)

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Reactions of Alcohols
Dehydration (Elimination)
● Water is removed from alcohol via elimination in a process called dehydration

○ In elimination reactions, two substituents of the molecule are removed
○ In this case it is the H atom and the OH group removed to form water
● Dehydration is carried out by heating it with concentrated acid, usually sulphuric acid
● An alkene and H2O are formed as products
● Tertiary alcohols dehydrate most readily, followed by secondary and then primary
○ Tertiary alcohols are the most reactive
○ Tertiary alcohols require the least heating to dehydrate, some can only need room
temperature
Dehydration of Ethanol to Form Ethene
Substitution with Hydrogen Halides (HX)
● An alcohol is converted to halogenated compound via a substitution reaction

● The hydroxyl group at a saturated carbon is substituted for a halogen
● R - OH + HX -----> R - X + H2O
● Tertiary alcohols are the most reactive, followed by secondary, then primary
2-methylpropan-2-ol / tert-butanol to 2-bromo-2-methylpropane and water

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● Hydrogen halide reactivity

○ The lower the bond enthalpy (average energy required to break a chemical bond) the
more reactive the hydrogen halide
○ Hydrogen halide reactivity increases as you go down the halogen group on the periodic
table
■ So from least to most reactive, (H-F) - (H-Cl) - (H-Br) - (H-I)
Oxidation
● In organic chemistry, electrons are transferred in the form of hydride ions (H-)
● OILRIG
○ Oxidation Is Loss (of hydrogen)
○ Reduction is Gain (of hydrogen)
● Reduction
○ When a carbon atom gains a bond to a hydrogen atom and loses a bond to an
atom greater than or equal to the electronegativity of carbon
○ Adding hydrogen atoms to a carbon increases the electron density around carbon
atom(s)
○ Consider the hydrogenation of ethene:
● Oxidation
○ When a carbon atom loses a bond to a hydrogen atom and gains a bond to an
atom greater than or equal to the electronegativity of carbon
○ Removing hydrogen atoms from a carbon decreases the electron density around
the carbon atom(s)
○ Consider the halogenation of methane:

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● Combustion = Oxidation
○ CH4 ---> CO2
Calculating Oxidation State of Carbon
● A carbon atom with its four valence electrons has an oxidation state of zero
● Each hydrogen atom bonded with the carbon adds another electron to the valence shell,
which decreases the oxidation state by one
● So, the oxidation state of methane would be -4
○ Since there are four (C-H) bonds
● A (C-O) will increase the oxidation state by one
● A (C=O) will increase the oxidation state by two
○ So methanoic acid would be -1+1+2
○ It is bonded to one H atom, one O atom and double bonded to another O atom
Production of Alcohols
● Alcohols can be produced by converting hydrocarbons to alcohols or they can be
produced from a renewable source such as the fermentation of crops
● Three main ways
○ Alkene hydration (Covered above)
■ The addition of hydroxyl (-OH) and (-H) when the double bond is broken
○ Substitution of halogenated organic compounds (Covered above)
■ The of the halogen side (-X) with a hydroxyl side group (-OH)
○ Fermentation
■ The enzymatic conversion (zymase) of carbohydrates such as glucose to
alcohols such as ethanol
Two different pathways of converting propene to an isomer of propanol

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Fermentation
● The process of converting simple sugars, like glucose, into ethanol in anaerobic
conditions
● Fermentation of glucose
○ Requires the enzyme zymase in yeast
○ Absence of oxygen
Conditions for Fermentation
● Yeast is temperature and pH sensitive

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○ General temperature range 15°C - 35°C

○ pH range 6.1 - 6.8
○ If conditions are too extreme, then the yeast will be denatured and the reaction
will not continue
● Fermentation occurs under anaerobic conditions / no oxygen gas present
○ Anaerobic pathway must be forced to produce ethanol
○ In the presence of oxygen gas, the ethanol can oxidise to ethanal and ethanoic
acid which are unwanted products
● Yeast cannot survive in ethanol concentrations greater than 15% (V/V)
○ When concentration reaches this level, the yeast is poisoned by ethanol and stops
the fermentation process
○ Yeast poisoning can be delayed by diluting the solution with distilled water
Producing Ethanol via Fermentation Prac
● Airlock used to prevent oxygen from entering

the apparatus
● CO2 escapes through the tubing of the airlock,
bubbling through the water and out through the
perforated cup
● Placed on a scale
○ When the mass is constant, fermentation
process has ceased
○ Because the CO2 escapes the apparatus, mass is lost
● After, the ethanol is extracted by first filtering out the sediments and then distilling the
mixture

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○ The more times the mixture is distilled, the greater the purity of the ethanol
● You can test to confirm if anaerobic fermentation is occuring
○ Connect the airlock filter with another tube to a solution of limewater
○ Use limewater test to confirm the presence of CO2
○ Limewater should turn milky-white colour
○ Ca(OH)2 + CO2 ----> CaCO3 + H2O
Saccharides
● Sugars belong to a class of organic compounds called saccharides

● They are cyclic carbohydrate structures containing multiple -OH groups and an oxygen
atom within the ring structure
● Glucose is a monosaccharide, it contains a single six membered ring structure
● Sucrose is a disaccharide containing the

monosaccharides glucose and fructose joined
together through a glycosidic bond

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● Disaccharide - two rings

● Trisaccharide - three rings
● Oligosaccharide - 3-10 rings
● Multiple monosaccharides and disaccharides can join to form very large structures, called
polysaccharides
● Cellulose is a polysaccharide containing repeated units of beta-glucose molecules
connected together through glycosidic bonds
○ The molecule connect via a condensation reaction of two hydroxyl side groups,
forming a glycosidic bond and a water by-product
○ (C6H10O5)n
○ Glucose minus Water = C6H10O5, because water is lost in the reaction
Hydrolysis of Polysaccharides
● Polysaccharides can be broken down into simpler saccharides by breaking the glycosidic
bonds and reintroducing water into the structure (hydrolysis)
● Cellulose must be broken down into simpler monosaccharides structures before it can be
fermented into ethanol
Hydrolysis of cellulose to form glucose: (C6H10O5)n + nH2O -----> nC6H12O6
● Hence, cellulose can be considered a raw material for ethanol production
● Disaccharides such as sucrose must be hydrolysed into monosaccharides before being

fermented
○ Hydrolysis of sucrose to form glucose and fructose
○ C12H22O11 + H2O -----> 2C6H12O6

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● Hence, sucrose from fruits and sugar cane are considered raw materials for ethanol
production
Oxidation of Primary and Secondary Alcohols

● Oxidation of alcohols is encouraged by using strong oxidising agents (readily reduced)
such as acidified permanganate ion (MnO4^-) or dichromate ion (Cr2O7^2-) solutions
● These oxidising agents undergo a colour change when they have been reduced
Deep Purple ------------------> Colourless
Orange ----------------->Green
● A colour change indicates that the alcohol has been oxidised

● The presence of (C-H) bonds are necessary for the organic molecule to undergo oxidation
Primary Alcohols
● Primary alcohols contain a carbon atom with 2 (C-H) bonds

○ So they can undergo oxidation twice
● Primary alcohols are oxidised to form aldehydes, which then oxidise to form carboxylic
acids
○ They lose a (C-H) each oxidisation
○ OILRIG
● The intermediate aldehyde usually cannot be isolated
○ Primary alcohols oxidise twice to form carboxylic acid
● However an aldehyde can be prepared from a primary alcohol by selecting a different
oxidising agent and solvent
○ Pyridinium chlorochromate or PCC (C5H6NCrO3Cl) in a dichloromethane
solvent (CH2Cl2) will predominantly oxidise the primary alcohol to the aldehyde
only

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Secondary Alcohols
● Secondary alcohols contain one (C-H) bond so it can undergo oxidation once
● They oxidise to form ketones
Tertiary Alcohols
● Oxidation will not occur because no (C-H) bonds are available
Half-Equations in Alcohol Oxidation
● Oxidation is the loss of carbon-hydrogen bonds

● Reduction is the gain of carbon-hydrogen bonds
Deduce the oxidation half-equation by:
1. Write the number of electrons lost

2. Balance the electrons of the oxidation and reduction half-equations
3. Balance the negative charge by adding the appropriate number of H+
4. Balance the hydrogen atoms by adding H2O to the appropriate side of the equation (used
when dealing with primary alcohol oxidation)

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CONCENTRATED ACID DEHYDRATES, DILUTE ACID HYDRATES
Fuels From Organic Sources and Biofuels

Throughout history, humans have used fuels to convert energy from one form into another and as
time has gone on, our fuel sources have become more efficient but also have caused increased
shifts in global climate
Fossil Fuels
● Our main source of fuel are fossil fuels

○ Fossil fuel sources include
■ Coal: used in the large scale production of electricity
■ Petroleum/Crude Oil: used to power internal combustion engines used in
vehicles and used in heating and cooking
■ Natural Gas (LPG): used to produce electricity and power certain engines
○ The build-up of atmospheric CO2 from burning fossil fuels makes a large
contribution to global climate change
○ But fossil fuels are nonrenewable so they will eventually have to be replaced with
alternative fuels that are renewable
■ Ethanol
■ Biodiesel
■ Biogas
Formation of Fossil Fuels
● Fossil fuels are fuels formed by the anaerobic decomposition of dead organisms under
high heat and pressure over millions of years
● The fuels are the gradual breakdown of plant and animal material buried into the Earth’s
lower levels where there is increased pressure and temperature
● The heat and pressure breaks the long carbon chains of biomass into shorter chains and
form the basis of fossil fuels
● These are then brought back towards the crust and can be accessed via mining and
drilling
Extraction of Energy From Fossil Fuels

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● Energy is extracted when the fuel is combusted, releasing large amounts of energy which
can be harnessed
● Energy is extracted since the hydrocarbons are moving into a more oxidised form
Extraction and Refining of Fossil Fuels
● Fossil fuels are extracted through mining (coal) or by direct drilling/pumping (oil)
● Once extracted they are refined and purified before being used
○ Fractional distillation
● After extraction and refining, there is often excess of higher chain lengths
○ Cracking is used to convert long-chain hydrocarbons into shorter, more useful
chains
○ Shorter chain hydrocarbons are used as fuels and within the petrochemical
industry
● Cracking is the breaking of carbon bonds to form short chain hydrocarbons
○ Two methods used to crack
■ Steam cracking involves the use of highly pressurised steam to cause
hydrocarbons to crack
● This was energy intensive
■ So it was replaced via the use of a catalyst (zeolites)
■ Zeolites are alumina silicates that have a large cage-like structure
● They act as a sieve and only allow certain sized molecules to pass
through them
■ When writing equations of cracking, include the catalyst, zeolites
Octane Rating
● Internal combustion engine works by first compressing fuel within a small chamber and
then igniting the fuel with a spark
● Certain fuels are prone to autoignition when compressed
○ This leads to knocking, which can damage an engine as it causes the timing of the
engine to be disrupted
● Octane rating is a measure of a fuel's ability to resist auto-ignition when compressed
○ It is measured by comparing the fuel to isooctane (rating 100) and heptane (rating
0)
● High octane rating → compress further before autoignition → better engine performance

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● The more branched hydrocarbon fuel is more resistant to auto-ignition, therefore higher
octane rating
● Octane rating decreases with carbon chain length
● To calculate octane rating of fuel
○ Take weighted average
○
Alternative Fuels (Biofuels)
● The major source of alternative fuels is biomass

○ Biomass is any organic matter that makes up a major component of a living
material
● Both plant and animal matter contain biomass that can be converted into fuel
○ The main components of plant and animal biomass that give them the potential
for use as a fuel are:
■ Cellulose
■ Fatty Acids
■ They both contain the base carbon and hydrogen that allows combustion
Bioethanol
● Ethanol is produced via fermentation of glucose in anaerobic conditions

● Renewable, made from crops
○ Fermentation of sugar cane, corn and wheat
○ Also can be produced via the waste of agricultural products
● However, the production of ethanol leads to the clearing of large amounts of land that
cannot be used for food production
● Benefits of using ethanol as fuel are:
○ Combusts readily and will release less CO2 than fossil fuels
○ High octane rating, very efficient fuel
○ Can be added to existing fuel in small amounts without any conversion of the
engine. E.g, E-10 is a petrol blend with 10% (v/v) ethanol
Biodiesel
● Diesel is a fuel mixture that contains many hydrocarbons normally of longer chain
lengths than conventional petrol
● Engines that use diesel rely on compression of the fuel igniting them (auto-ignition)

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● Diesel has better efficiency than traditional fuels and so is used in trucks and large
vehicles
● Biodiesel is a diesel fuel created from transesterification of a vegetable oil or animal fat
○ It is a mixture of esters with long hydrocarbon chains
○ These esters are produced by a chemical reaction between vegetable oils or
animal fats and an alcohol
○ Triglyceride + Alcohol → Glycerol + Ester (biodiesel)
■ In alkali conditions
● Benefits of using biodiesel as fuel are:
○ Can be produced from waste products in agriculture and farming, renewable
○ Little difference in fuel efficiency to fossil fuels
○ Produces less net carbon than regular diesel
Both bioethanol and biodiesel are formed from plant (or animal) matter and plant matter is formed from
photosynthesis where CO2 is removed from the atmosphere.
Fossil fuels only release CO2 and do not remove any from the atmosphere, so bioethanol and biodiesel
cause a lower net increase in the amount of CO2.
Biogas
● Biogas is a type of biofuel produced during the decay of biomass

● As plant and animal matter decay, with the assistance of anaerobic bacteria, they release
methane, CO2, and small amounts of hydrogen sulphide
● Capturing these gases allows us to use them as fuel
○ Methane is a strong greenhouse gas and capturing it can control the enhanced
greenhouse effect
● Biogas can be used for heating and cooking
● Formation of biogas takes place via anaerobic digestion
○ Similar to fermentation
○ Performed by microorganisms in the absence of oxygen
○ 1. Hydrolysis - conversion of large hydrocarbons into simple sugars (glucose) or
amino acids
○ 2. Acidogenesis - further breakdown of sugars and carbohydrates into volatile
fatty acids
○ 3. Acetogenesis - conversion of volatile fatty acids into acetic acid, CO2 and H2
○ 4. Methanogenesis - conversion of acetic acid into methane and CO2 (with
consumption of H2)

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Reactions of Organic Acids and Base

Inquiry Question: What are the properties of organic acids and bases?
Aldehydes and Ketones

● A ketone and aldehyde both contain a carbonyl group (C = O).
● Aldehydes have the (C = O) attached to an R group and a hydrogen atom
○ When R is an alkane, the general formula of an aldehyde is CnH2n+1CHO
○ They have the suffix -al at the end of the name
● Ketones have the (C = O) attached to two R groups

○ When both R groups are alkanes, the general formula of a ketone is CnH2nO
○ They have the suffix -one at the end of the name

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● Corresponding aldehydes and ketones are functional group isomers
Properties of Aldehydes and Ketones
● Carbonyl (C = O) is a polar group and governs the properties of aldehydes and ketones
○ The carbon is slightly less electronegative, oxygen is slightly more
electronegative
● Dipole-dipole forces form between molecules of aldehydes and between molecules of

ketones due to the polar (C = O) group
● Similar to alcohols, the alkyl parts of the molecule still retain its non-polar nature
○ The influence of the carbonyl group decreases as the length of the carbon chain
increases
○ Because the non-polar part of the molecule begins to dominate the nature of the
molecule
● Dipole-dipole forces, therefore aldehydes and ketones have a higher B.P than their
corresponding alkanes of similar molar mass
○ But lower B.P than alcohols because of their H-Bonds
● Small aldehydes and ketones, such as methanal, ethanal and propanone are soluble in
water due to the polar interaction between water and the carbonyl group
○ In smaller aldehydes and ketones, the polar (C = O) dominates the nature of the
molecule
○ Larger aldehydes and ketones are not soluble in water
○ Aldehydes and ketones are less soluble than alcohols as they have hydrogen
bonds
Carboxylic Acids
● Carboxylic acids contain the carboxyl (-COOH) functional group
● When the R group is an alkane, the carboxylic acid is called an ‘alkanoic acid’
● The general formula is CnH2n+1COOH
● They end in -oic acid

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Physical Properties of Carboxylic Acids
● Carboxyl group (-COOH) is a polar group and governs the properties of carboxylic acids
● Dipoles form about the carboxyl group
● It participates in H-Bonds and Dipole-dipole forces
● Similarly, the influence of the carboxyl group decreases as the length of the carbon chain
increases
○ The non-polar part of the molecule begins to dominate the nature of the molecule
● The carboxyl group is made up of two polar groups, the (C = O) and (-OH) group
○ This enables carboxylic acids to exist as dimers, held together by 2 H-Bonds
○ Due to this dimerisation, carboxylic acids have a higher B.P than their
corresponding alkanes, aldehydes, ketones and alcohol
● Small carboxylic acids like methanoic and ethanoic acid are very soluble in water
○ This is due to its H-Bonds
● Larger carboxylic acids are not soluble in water
○ Non-polar part begins to dominate the nature of the molecule
○ Large carboxylic acids line up at the surface of the water with only the polar
group immersed in the water
Amines
● Amines contain the amino (-NH2) functional group

● Amines are compounds in which one or more of the hydrogen atoms in NH3 are replaced
by a carbon-containing group
○ Amines are derivatives of Ammonia

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● They end in -amine

● When naming, indicate the alkyl group positions on the nitrogen by writing N in front of
the prefix names
Physical Properties of Amines
● The amino group (-NH2) is polar and governs the properties of amines
● Nitrogen is the third most electronegative element after fluorine and oxygen, so the amine
functional group is very polar and primary and secondary amines can form H-Bonds
● Tertiary amines cannot form H-Bonds because there is no N-H bond in the molecule
● As the length of the carbon chain increases, the influence of the amino group decreases
because the non-polar part of amine begins to dominate the nature of the molecule
● Lower B.P than alcohols,
○ Because nitrogen is less electronegative than oxygen, the H-Bonds are weaker
than alcohols’ H-Bonds
○ Tertiary alcohols cannot participate in H-Bonds and therefore have lower than
those of primary and secondary amines
● Smaller primary and secondary amines are soluble in water
○ H-Bonds enables small primary and secondary amines to dissolve in water
○ Tertiary amines cannot participate in H-Bonds, generally insoluble
Amides
● Amides are derivatives of carboxylic acids and amines
○ They are formed when the (-OH) group is replaced by an amino group
● The covalent bond between the carbonyl carbon, and the nitrogen atom is called a peptide
bond - a fundamental bond in connecting together amino acids to form proteins
(polypeptides)
● End in -amide

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● Indicate the alkyl group positions on the nitrogen by writing N in front of the prefix
names
Physical Properties of Amides
● Primary and secondary amides have two very polar constituents about the peptide bonds,
the (N - H), and the (C = O) groups
● Primary and secondary amides form H-Bonds between molecules
● Amides can also form dimers with H-Bonds forming between the (N - H) and (C = O)
constituents of different amide molecules as shown below
● Tertiary amides do not contain a (N - H) component since the nitrogen is completely

substituted and as such cannot form any H-Bonds
● As molar mass increases, the physical properties of amides become more similar to
hydrocarbons of similar molar mass
● The B.P of amides do not trend predictably with molecular weight like alcohols, amines
and carboxylic acids
○ The H-Bonds between amide molecules can take on intricate and complicated
designs resulting in much higher interaction between the molecule than for
example dimerisation
■ Intricate H-Bond Networks

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○ E.g Ethanamide can exist in a ladder formation that gives it a much higher B.P
and M.P than an alcohol, amine or carboxylic acid with the same molar mass
● Smaller primary and secondary amides are soluble in water
○ H-Bonds
○ Larger molecules are not soluble in water
○ Tertiary amides cannot participate in H-Bonds and are insoluble in water
Esters
● Esters are a group of organic compounds responsible for flavours and fragrances of many
fruits and flowers
● In esters, an alkyl group replaces the hydrogen atom in a
carboxyl group
● Esters are formed via a condensation reaction between a
carboxylic acid and an alcohol
● carboxylic acid + alcohol ⇌ ester + water

● The (-OH) component of the carboxyl group and the hydrogen atom of the hydroxyl
group react to form an ester bond and a by-product of water - hence condensation
● Esters can also be found in industry for artificial flavouring and colourings
Naming Esters
● alkanol + alkanoic acid ⇌ alkyl alkanoate + water
1. The alkyl group bonded to the oxygen is named first, the part derived from the alcohol
2. The second part of the name comes from the parent carboxylic acid. The suffix -ic acid is
replaced with -ate

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Physical Properties of Esters
● Dipoles form about the ester group due to the difference in electronegativities of oxygen
and carbon
● Dipole-dipole interactions
● No H-Bonds between ester molecules, there are no positive dipoles about hydrogen
atoms
● As molar mass increases, the physical properties of esters becomes more similar to
hydrocarbons of similar molar mass
● Esters can form H-Bonds with water molecules
○ The oxygen atom of esters act as a hydrogen bond acceptor which confers to some
water-solubility

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● Esters are less soluble in water than the corresponding alcohol and carboxylic acid
○ Esters are not H-Bond donors
○ They don’t have a hydrogen atom with a positive dipole to participate in H-Bond
with water
● Esters have high solubility in non-polar (organic) solvents
○ Esters have a non-polar alkyl component
● Higher B.P than the corresponding hydrocarbon but lower B.P than corresponding
alcohols and carboxylic acids
○ Dipole-dipole forces
Preparing an Ester
● Ester formation is a slow and reversible process

● carboxylic acid + alcohol ⇌ ester + water
● To viably produce esters, the reaction rate and yield must be optimised
○ The reaction rate is increased by
■ Using an acid catalyst such as sulphuric acid
■ Heating the reaction mixture under reflux
○ The yield is increased by driving the equilibrium position forward
■ Having excess reactant
■ Removing water from the equilibrium
system
Increasing Reaction Rate of Esterification
● Small amounts of sulphuric acid will sufficiently

catalyse an esterification reaction
● While heating increases the reaction rate, it also
results in evaporation of the volatile components in
the reaction mixture

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● To prevent the loss of volatile components, a reflux process is used in esterification

○ The components of the mixture are heated via reflux to prevent losses to
evaporation
○ The longer the mixture is left to reflux, the more the reactants will have converted
to products
● Water bath on a hot plate
○ Evenly heats mixture
○ Indirect heat
● Boiling chips required
○ Bumping due to superheating is avoided and even boiling is promoted
Increasing Yield of Esters
● The equilibrium must be driven forward to improve the yield

● Excess alcohol is used to drive the reaction forward and increase the yield of ester
○ Explained by LCP
○ Carboxylic acid can also be used, but it depends on what is more economically
viable
● Water is not a good solvent in esterification
○ It will favour the reverse reaction (hydrolysis)
○ If it is removed from the system it will drive the equilibrium reaction forward
■ LCP
○ It can be removed through drying agents such as magnesium sulphate
Safety Hazards in Esterification
● Organic compounds are flammable

○ Use a hotplate or heating mantle instead of Bunsen
○ Keep organic compounds away from naked flame
● Vapours from organic chemicals can be toxic
○ Check MSDS
○ Conduct experiment in well-ventilated room and in fume cupboard
● Gases can build up in the neck of the round bottom flask
○ Do not stopper the top of the condenser during reflux
● Concentrated sulphuric acid is corrosive
○ Wear PPE, lab coat, goggles, gloves, and closed shoes
Separating and Purifying Esters

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● Once reflux has been performed, the flask will contain a mixture of various compounds
○ These are separated with differences in water solubility and B.P
1. Neutralising the acidic constituents via sodium carbonate

● The sodium salt product makes it completely soluble
2. Separating out the oil layer via a separating funnel

● The mixture is poured into a separating funnel
● Distilled water is added to ensure the water soluble content has been dissolved
● The oil will end up on top (less dense) and the water soluble content will be on
the bottom (more dense)
● The aqueous phase will contain the water soluble substances such as
○ Sulphuric acid
○ Ionic salts
○ Leftover carboxylic acid and alcohol
● The oil phase will contain almost exclusively the ester
● To ensure that the top layer is oil phase, add several drops of water and observe
whether it passes through the top layer or dissolves into it
3. Purifying the ester via distillation

● The ester and the other constituents in the oil phase can be separated by
distillation due to differences in B.P
Uses of Esters
● Esters being flavour agents and having strong smells/fragrances can be used in many
industries
● Perfume making and food
● Wine - ethyl ethanoate is the ester condensed through ethanol and ethanoic acid
● Esters are also used as preservatives in food
○ Parabeus (ester of hydroxybenzoic acid) used for its antimicrobial properties
○ Synthesised with para-hydroxybenzoic acid and alcohols like methanol, ethanol
etc
● Esters are also naturally found in many foods like fruits and even in our bodies as the
proteins that make up human DNA and RNA

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Fats and Triglycerides (Triesters)
● Triglycerides belong to a naturally occurring group of organic compounds called lipids,

commonly referred to as fats or oils
● Triglycerides are triesters of the alcohol glycerol (propane -1,2,3 -triol) and three long
chain carboxylic acids (fatty acids)
● Fatty acids can be removed from
triglyceride via hydrolysis
○ The ester bonds break,
cleaving off glycerol and three
fatty acids
Soaps - Salts of Fatty Acids
● Soaps and detergents are generally used as cleaning products because of their ability to
remove dirt, oil and stains.
○ This is due to the structure of soap and detergent molecules
● Soaps are salts of fatty acids
○ Triglyceride + NaOH → glycerol + sodium salts of fatty acids (soap)
● They consist of a long hydrocarbon chain/tail with a carboxylate ion (COO-) as the head
○ The hydrocarbon tail is non-polar and is hydrophobic
○ The carboxylate head is ionic and is termed hydrophilic
○ This dual nature of soap molecules enables soap to interact with both polar and
non-polar substances
● Reduced cleaning ability in hard water as hard water contains high [Ca2+] and [Mg2+]
○ They form a precipitate with the carboxylate head and
○ This prevents it from forming its ion-dipole interactions with water
○ Hence the dual nature of the soap molecule is reduced and cleaning ability is
reduced

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Micellization - Cleaning Action of

Soaps
● Grease or dirt that couldn’t be

cleaned with water is typically
non-polar
● Soaps are able to remove grease
using a water solvent via a process
called micellization
● MUST DRAW HEADS RIGHT
ON TOP OF GREASE -MUST
BE TOUCHING
● Each micelle is surrounded by

negatively charged heads so they
will repel each other and prevent the
grease from aggregating during the
wash
● Also, due to the small size of the micelles, they remain suspended in the water and can be
washed away
Saponification
● Saponification is the process by which soap is made

● The fatty acid is isolated from a triglyceride through hydrolysis
○ The hydrolysis of triglycerides is undertaken in an alkaline solution
○ The mixture is heated and the ester bonds break forming glycerol and
deprotonated fatty acids

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● NaOH is commonly used as the base in saponification

● To extract the soap, concentrated sodium chloride solution is added which forces the soap
to curdle at the surface of the mixture where it can be scraped out
● Adding the salt causes the water molecules to prefer to arrange about the sodium and
chloride ions instead of the soap molecules
Preparation of Soap In School Lab
1. Mix 50mL of oil/fat (e.g olive oil) with excess NaOH solution.
2. Add 10mL of methylated spirits to help emulsify the oil/fat into micelles so that there
will be a greater surface area in contact with the NaOH, and hence an increased rate of
reaction.
3. Heat mixture in a water bath and stir
4. Add 30mL chilled saturated NaCl solution to precipitate the soap curds (common ion
effect)
5. Filter the soap curds and wash with deionised water.
6. Dry the soap curds on filter paper.
1. Various vegetable oils or chopped up fats are heated with 30% NaOH until all the fat is
dissolved
2. The solution is cooled and mixed with brine
3. Mixture settles into 2 layers, curd of soap on top, solution of glycerol on bottom
This process is called ‘salting out’ the soap

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This causes precipitation to form by increasing the concentration of ions in solution.
Detergents
● Detergents are synthetically made soap molecules

● Hydrophobic tail, hydrophilic head
● The difference between soaps and detergents is found in the structure of the hydrophilic
head
● There are three main classes of detergents
○ Anionic detergents
○ Cationic detergents
○ Non-ionic detergents
Anionic Detergents
● Similar to soaps, anionic detergents have a negatively charged ion as the head of the
molecule
○ A sulphonate head
○ Still effective in hard water
● Form soluble complexes with Mg and Ca instead of soap scum

● Relatively cheap
● Have a good a lather
● Harsh action
● Effective in hard water
● Common uses include:
○ Laundry detergents
○ Dishwashing detergents

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○ Household cleaners
Cationic Detergents
● Cationic detergents have a positively charged ion as the head of the molecule
○ Have a quaternary ammonium head
○ Effective in hard water
● The positively charged heads do not form any attractive forces with Mg and Ca
● Relatively expensive
● Bond strongly to negatively charged surfaces such as hair or clothing material
● Kills bacteria
● Some common uses include:
○ Fabric softener
○ Hair conditioners
○ Disinfectants
○ Antiseptic wash
Non-Ionic Detergents
● Non-ionic detergents have a polar head

that is not charged
● The structure can vary and become quite
complex
○ Non-ionic detergents usually have polar functional groups in the head
○ Effective in hard water
● Head carries no charge

○ Minimal interaction between the nonionic head and Mg and Ca in hard water

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● Relatively expensive
● Low lathering ability
● Common uses include:
○ Dishwasher detergents
○ Glass cleaners
○ Emulsifying agent in food items and pharmaceuticals
Soaps and Detergents as Surfactants
● A surface active agent or surfactant is able to decrease the surface tension between the
interfaces of liquid-air, liquid-liquid, and liquid-solid
● Water has a high surface tension
○ Strong H-Bonds
● Water droplets on non-polar plastic material bead instead of spreading out
○ Cohesive forces of water are stronger than adhesive forces of water at the
interface
○ Liquid will wet a surface if there are strong intermolecular attractions between the
liquid and the surface
● Soaps and detergents will interact with water at the liquid-solid interface
○ Dissolving soaps or detergents in water will lower surface tension of the water
○ Disrupts H-Bonds
○ Lowers surface tension of water
○ The water spreads out onto the surface rather than remaining in a droplet
Emulsifying Agents
● An emulsion is a mixture of two or more liquids that are normally immiscible

○ Requires a surfactant to stabilise it to form micelles which can be dispersed
throughout the solvent
○ Soaps and detergents allow for oil and water to mix together because they reduce
the surface tension at the liquid-liquid interphase
● A surfactant is an emulsifier
● When water is the predominant solvent
○ The emulsion is categorised as an oil-in-water emulsion
○ Like micelles in the cleaning action of soaps
● When oil is the predominant solvent
○ Emulsion categorised as a water-in-oil emulsion
○ E.g Butter

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○ Paint is a very common emulsion containing coloured particles which are

dispersed in a carrier such as water, hence water-based paints
Reaction Pathways
Polymers

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Inquiry question: What are the properties and uses of polymers?
Polymers
● Molecules that have 1000s of atoms per molecule are called macromolecules
○ They have large molar masses
○ Varying degrees of solubility in water
● A polymer is a macromolecule that is made up of identical repeating units called
monomers linked via covalent bonds
● The process of linking monomers to form the polymer is called polymerisation
● Synthetic polymers are referred to as plastics
○ Plastics can be divided into two major types
■ Thermoplastics
● Can be continually melted and remoulded many times
■ Thermosetting plastics
● Moulded when they are first made
● Alkane - 1 sigma bond (least reactive)
● Alkene - 1 sigma bond, 1 pi bond
● Alkyne - 1 sigma bond, 2 pi bond (most reactive)
● Sigma - Strong
● Pi - Weak
Polymer Notation
E.g Ethene/Ethylene
The polymer that forms from this monomer is called polyethylene

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Common Polymers
Monomer Name Monomer Systematic Name Polymer Names
ethylene ethene polyethylene
propylene propene polypropylene
Vinyl chloride chloroethene polyvinyl chloride (PVC)
1,1-dichloroethylene 1,1-dichloroethene poly(1,1-dichloroethylene)
Acrylonitrile propenenitrile polyacrylonitrile, acrylics
tetrafluoroethylene tetrafluoroethene poly(tetrafluoroethylene),

PTFE, Teflon
styrene ethenylbenzene polystyrene, Styrofoam
Polymer Chain Arrangements
The shape of the chains is a determining factor in the polymer’s properties.

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Properties of Polymers
● Properties of polymers depend on their chain structure and the intermolecular forces
between chains
Crystallinity
● A crystalline region of a polymer is a region in which the polymer chains are linear and
able to tightly compact
● When the degree of crystallinity is high, the polymer chains can compact and get close to
each other, increasing the strength of the intermolecular forces
○ Highly crystalline polymers have high M.P, are opaque, rigid and have high
densities
○ Highly amorphous polymers (tangled/non-linear) have low M.P, are transparent,
flexible and have low densities
■ Backbiting
■ Open space regions
Branching
● In a highly branched polymer, the chains are unable to compact, thus reducing the
strength of the intermolecular forces between the chains
○ Highly branched polymers tend to be amorphous
○ Produced in plastics that are created under high temperatures
Chain Length
● Chain length is a measure of the average number of monomer units per chain
● Higher chain lengths result in greater molecular mass and thus greater intermolecular
forces
○ Higher M.P and more rigid plastic
Side Groups
● Side groups can be attached to the main chain of a polymer, affecting the ability of the
chain to flex and move
● The larger the side group, the less flexible the polymer is
Cross-Linking

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● Cross-linking occurs when chains are connected in 2 or 3 dimensions

● The greater the amount of cross-linking, the more rigid the polymer
● It is a connection across chains with covalent bonds rather than intermolecular forces
Addition Polymerisation
● Addition polymerisation involves sequential addition reactions of an unsaturated or

reactive monomer (e.g ethylene) to form a polymer that
retains all molecules
● Addition polymers are most commonly found in
synthetic polymers formed from ethylene and its
derivatives
● Ethylene can undergo various reactions to form the
monomers used in a wide variety of plastics
Radical Chain-Growth Polymerisation
● This form of addition polymerisation involves the use of radicals (a molecule with one
more unpaired electron)
● The polymerisation reaction occurs over 3 steps
1. Chain Initiation
2. Chain Propagation
3. Chain Termination
Chain Initiation
● A radical is produced which in turn causes the first monomer unit to become activated
● An initiator molecule such as an organic peroxide or oxygen radical reacts with a single
monomer unit
○ It contains a free radical which causes the double bond in the monomer to break
and form a new bond between the initiator and monomer
○ There is an electron from the double bond which remains unpaired and results in a
new radical forming
Chain Propagation

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● The radical will react with another monomer, causing the double bond to break result in
another radical forming
● This process continues to build up a chain
Chain Termination
● Once enough monomers have combined to form a long chain the chain propagation can
be stopped by removing the radical nature of the polymer ends
● It can be terminated by the addition of 2 chains with radical ends forming a bond called
coupling
● Or through the reaction with another radical molecule which can cap the molecule
The Polymerisation of Ethylene Derived Monomers
● The chain propagation of ethylene derived monomers occurs to favour a head-to-tail

arrangement
Types of Addition Polymers
Low-Density Polyethylene (LDPE)
● Commercial production of polyethylene with the use of a peroxide catalyst produces a

strong, soft plastic called LDPE

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○ At temperatures of 500°C
○ Pressures in excess of 1000 x 10^5 Pa = 900 atms
● Low density (0.92gcm^-3)
● Low M.P (105-115°)
○ Therefore, not suitable for use in situations where the heat approaches the boiling
point of water.
○ Commonly used a plastic wrap due to high flexibility and transparent nature
○ Highly-branched LDPE
■ Chains cannot compact
■ Amorphous polymer
High-Density Polyethylene (HDPE)
● HDPE is produced using the Ziegler-Natta chain growth polymerisation

○ Highly-active heterogeneous catalyst used to aid growth
○ Occurs at lower temperatures and
pressures than LDPE
● Rigid plastic
● Higher M.P (133°C) due to its unbranched
nature
● HDPE is used in the production of plastic
bottles, corrosion-resistant piping,
geomembranes and plastic lumber.
Draw the polymers, at least 3 carbons

Show the stacking and lack of stacking
Polyvinyl Chloride (PVC)
● PVC is made from the addition polymerisation of the monomer vinyl chloride
(chloroethene)

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● PVC forms an amorphous polymer

○ However, it is rigid
■ Chlorine side group is highly electronegative, forming dipoles within the
polymer chains
■ This leads to the formation dipole-dipole forces between polymer chains
■ This holds the chains tightly together
● Used in pipes, wire and cable insulation
● To prevent UV degradation
○ Cover the PVC pipe with PVC primer
○ Paint the PVC pipe with water-based latex paint.
Polystyrene
● Made from the addition polymerisation of the monomer styrene (ethylbenzene)

● Amorphous polymer but hard and brittle
○ Due to its side group which prevents the close packing of polymer
○ However, the size of the side group also stops the chains from bending and
moving apart
○ The large side group locks the chains together and inhibits their movement
○ Hence, it is rigid
● Polystyrene is used to create Styrofoam
○ Air is blown into setting plastic and creates many air pockets
○ Making the plastic very lightweight but still strong
○ It also has insulating properties
Polytetrafluoroethylene (PTFE/Teflon)
● PTFE is made from the addition polymerisation of the monomer tetrafluoroethylene

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● Commonly known as Teflon by its inventors

● Thermoplastic - High density - High M.P
● Used to coat non-stick cooking wear due to its unreactive nature
● Also used as an insulator in high end wire used in the aerospace industry
● Excellent insulator
○ Able to shield wires from electrical and magnetic interference
Polyvinyl Acetate (PVA)
● PVA is an addition polymer

made from the monomer vinyl acetate (ethenyl
ethanoate)
○ The monomer is prepared with ethylene
○ Ethylene is reacted with acetic acid (ethanoic acid) and oxygen gas to produce
vinyl acetate
● Commonly used as an adhesive or as a fabric
● PVA can form dipole-dipole forces across chains
● Amorphous and flexible
Importance of Ethylene
Ethylene is an alkene derived from the fractional distillation of crude oil. The double bond within
the ethylene makes it suitable as a precursor chemical. It is used to produce monomers such as
vinyl chloride (via halogenation) and styrene (via substitution of benzene). In addition, it can
undergo hydro esterification to form vinyl acetate.
The flexibility of ethylene makes it an important chemical in industry.

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Condensation Polymerisation
● Condensation polymers are polymers formed by the reaction between monomers which
result in the loss of a small molecule (by-product)
○ It is the reaction between different functional groups within the monomers
● Two standard condensation polymer reactions
○ 1. A single monomer of the form A - R - B
○ 2. Two monomers of the form: A - R - A and B - R* - B
● A and B represent some reactive functional group
○ E.g (-OH) (-NH2) (-COOH) (-COCl)
○ When the monomers that combine are different, the product is a copolymer
Types of Condensation Polymers
Polyesters
● Polyester is a condensation polymer

where each monomer unit is joined
via ester bonds
● The monomers are a diol and a
dicarboxylic acid
● A water by-product is released
● Used in textiles, packages, carpets,
rugs
● Polyethylene terephthalate or PET

● Formed from the polymerisation of benzene-1,4-dicarboxylic acid (terephthalic acid) and
ethane-1,2-diol (ethylene glycol)
● PET is used in the production of bottles and can be recycled
● Several polar sections, strong dipole-dipole
interactions
○ High M.P
● Very few side groups that come off the main
carbon chain
○ Thus, should be able to form a crystalline
plastic (not as much as PVC or Styrene)

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Polyamides and Nylons
● A polyamide is a condensation polymer where each monomer unit is joined via amide
links
● The monomers are a diamine and a dicarboxylic acid or amino acids
● The polyamide reaction forms an amide bond (called a peptide bond in proteins) through
the reaction of the two monomers
● Used for clothing fabric, rope, luggage, umbrellas
● Proteins are natural polyamides
● Nylon is the most common synthetic polyamide
● Nylon naming
○ Nylon-X,Y is formed from diamine with a carbon chain X and dicarboxylic acid
of length Y
○ E.g Nylon-5,10 is made from a diamine with 5 carbons and a dicarboxylic acid
with 10 carbons
● Nylon-6,6 is a common form of nylon used
in the manufacture of synthetic fibres
○ Monomers are:
■ Hexane-1,6-dioic acid
■ Hexane-1,6-diamine
Proteins
● A protein is a macromolecule that consists of one or more long chains of amino acids that
are joined by peptide bond, also called polypeptides
● Protein functions:
○ Acts a catalyst for certain metabolic reactions
○ Replication of DNA and RNA
○ Provides a messaging mechanism for stimuli response
○ Provides structure to cells
○ Transports molecules within cells
● Proteins are unique sequences of amino acids
○ The amino acids act as the monomer unit, but unlike polymers, the amino acids
pattern is specific to the protein and is dictated by a nucleotide sequence
● Protein structure is described using 4 levels:
○ Primary Structure refers to the amino acid sequence. It is held together by the
peptide bonds

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○ Secondary Structure refers to how various sections of the polypeptide backbone

orientates themselves into a pattern or specific shape. It is governed by the
strength of H-Bonds that form
○ Tertiary Structure refers to the 3D shape of the entire protein. It is governed by
the hydrophobic and hydrophilic interactions of sections of the protein
○ Quaternary Structure refers to the way in which multiple polypeptide chains come
together to function as a single unit. There can be several quaternary structures for
a given set of subunits, which in turn gives the same protein several possible
functions

Chemnotes Mod 7

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Chemnotes Mod 7

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Module 7 Chemistry Notes

Chemistry- Unit 4 (High School - Australia)

Studocu is not sponsored or endorsed by any college or university

MODULE 7:​ ​Organic Chemistry

Homologous Series Main Features

Alkanes Hydrocarbon chains containing only single bonds (C - C)

Alkenes Hydrocarbon chains containing a carbon-carbon double bond

Alkynes Hydrocarbon chains containing a carbon-carbon triple bond

Alcohols Contain a hydroxyl (-OH) functional group

Aldehydes and Ketones Contain carbonyl group (C=O)

Carboxylic acids Contain a carboxylic acid functional group (-COOH)

Amines and Amides Contain Nitrogen (N) atom in the chain

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Naming Organic Compounds

Prefix​ + ​Parent​ + ​Suffix

No. of Carbons Parent Names

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Primary, Secondary and Tertiary

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● Functional Group Isomers

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Alkyl Side Groups

conduct an investigation to compare the properties of organic chemical compounds within a

Shape of Molecules Formed Between Carbon Atoms

The nature of bonding around each carbon

The molecular arrangement can influence

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Physical Properties of Hydrocarbons

Physical Properties of Alkanes

● The only type of intermolecular force

● At room temperature- C1 to C4 are

● Insoluble in water​ and ​Dissolve

● The​ ​shape of the hydrocarbon also influences B.P and M.P

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Physical Properties of Alkenes and Alkynes

● Similar to their corresponding alkanes​ (same number of carbon atoms).

Cyclic Hydrocarbons (Cyclo...)

● Non-polar and share similar

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● Aromatic hydrocarbons contain one or

Naming Halogenated Organic Compounds

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● In haloalkenes and haloalkynes, the multiple bond takes priority

Safety When Handling and Disposing Organic Substances

● Chronic/Long-Term Health Effects

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● Flashpoint​ - The lowest temperature at which a liquid will ignite

● Conduct experiments with organic compounds in well-ventilated rooms where there

Disposal of Organic Compounds

Environmental, Economic and Sociocultural Implications of

The most significant reaction that hydrocarbons undergo is ​combustion.

● The first fuel sources to be exploited were wood and peat

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○ These all had a higher energy density than wood

Fractional Distillation of Petroleum (Crude Oil)

● Petroleum is a complex mixture of

1. Petroleum mixture is heated to a high

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● Short chain molecules condense toward the top of the column

Fraction Name Use

Gas Used in LPG for cooking and heating.

Ethers Solvents in industrial reactions.

MODULE 7: Organic Chemistry

Prefix + Parent + Suffix

● Insoluble in water and Dissolve

● The shape of the hydrocarbon also influences B.P and M.P

● Similar to their corresponding alkanes (same number of carbon atoms).

● Flashpoint - The lowest temperature at which a liquid will ignite

The most significant reaction that hydrocarbons undergo is combustion.

1. Using q=mCΔT find how much heat the water absorbed

● Water is removed from alcohol via elimination in a process called dehydration

● An alcohol is converted to halogenated compound via a substitution reaction

Deep Purple ------------------> Colourless