Chain isomers when we make branches

Positional isomers moving of double bonds (the functional group)

Functional isomers going from alkene to cycloalkane going from 1 functional group to another
Geometric isomers two different groups around a double bond with restricted rotation
Optical isomers when non-superimposable mirror images of the same molecules are present
Optical isomers are non-superimposable mirror images of each other and these arise from something
called chiral centers which contain 4 different groups of atoms, to exist as non-superimposable

To calculate the number of optical isomers a molecule has we

do 2^n so the n being the number of chiral centers so 2 to the
power of the number of chiral centers.

Need to know how to draw a 3d image of a molecule remember an atom facing directly your way has
a triangle while an atom facing to the right or left has dotted/slashed lines. These two molecules are
enantiomers which are non-superimposible mirror images of each others.
The * shows that both the molecules are enantiomers of each others
We first polarise our unpolarised light into a plane-polarised light then pass through a tube containing
a sample of compound if the sample of compound is optically active, the plane of polarisaiton os
rotated. Laevo is clockwise and Dextro is aiticlockwise
As you can see from this diagram the sample
compound as it is an optically active substance it
causes rotation
So we say that a chiral compound can cause the plane polarised light to
be rotated. As such a compound is optically active.

Two enantiomers have the same physical properties except for their plane-polarised light rotation
Two enantiomers also have the same chemical properties except in the way they react with
ENANTIOMERS OF OTHER SUBSTANCES
A sample of a compound can contain a mixture of both enantiomers so the effects of the enantiomers
on the plane-polarised light will cancel each other out. If we have our plane polarised light 1 of them
would rotate anti-clockwise and the other plane polarised light would rotate clockwise and so you are
cancelling out both of the effects. And if we have this in equal amounts we form a racemic mixture,
and these racemic mixture shows no optical activity because it has an equimolar mixture of
enantiomers.

These are nucleophic substitution reactions and 1 is unimolecular and one is bimolecular and that is
all to do with the rate determining step. Sn1 means 1 species is involved in the RDS and seen for
tertiary halogenoalkanes. Whereas Sn2 has 2 species involved in the RDS and seen for primary
halogenoalkanes. So we can use optical activity of reactants and products as evidence
for Sn1 and Sn2 mechanisms
The ketone is a trigonal planar so it can be equally attacked from either
side of the molecule with a CN- (cyanide ion). Forming a racemic mixture

As we can see in this Sn2 reaction between primary halogenoalkanes and nucleophiles this creates a
transition state first. This Sn2 reaction is a one step reaction. Also in this reaction the arrangement of
the remaining 3 groups is inverted therefore the optical activity of the product must be different to
reactant. As the product has now become non-superimposible this difference in optical activity one
rotating clockwise and other anti-clockwise and we can test this by using polarised light to this sample
of product before and after nucleophilic substitution and we shall see a difference in the optical
activity.

Sn1 reaction which is a 2 step nucleophilic substitution reaction between tertiary, secondary
halogenoalkanes can form 2 different kinds of products depending on where the nucleophile attacks
the trignonal planar carbocation. And it will form enantiomers as they are non-superimposible where
the OH group is inverted.

Sn1 reactions are also with tertiary HALOGENOALKANES, where only 1 species is in the rate
determining step meaning the initial reaction is slow (a rate determining step). The mechanism is also
a 2 step reaction.
So in Sn1 nucleophilic substitution reactions as due to the halogenoalkanes tetrahedral shape and the
fact that it forms a Trigonal Planar Carbocation this means that there is an equal chance of attacking
HO^- ion approaching from the left or the right. This means that the two products, that are
enantiomers, can be formed with 50:50 concentrations thus as these enantiomers are present in
equal numbers due to the Planar Carbocation formed from the tetrahedral shape of halogenoalkane
the reaction would form a racemic mixture so there will be no evidence of optical activity.

On the contrary the Sn2 nucleophilic substitution when using a polarised light gives a change in
optical activity giving evidence for the presence of an Sn2 reaction while in Sn1 reaction there will be
no optical activity as the tetrahedral shape of the halogenoalkane and the Planar Carbocation gives it
a racimic product with no optical activity
Aldehydes and Ketones contain carbonyl groups these Carbonyl groups are made up of C=O
Carbonyl group attached to the centre of the carbon chain
Both aldehydes and ketones have distinct smells the Ketones tend to smell like solvents such as nail
polish remover. While the aldehydes varry in their scent depending on their chain lengths they can
smell like rancid butter or like roses.
Both aldehydes and ketones have London forces as well as permanent dipole-dipole interactions from
the C=O bond. Boiling temperature of carbonyls increase as molar mass increases due to increased
London forces. The aldehydes have higher temperature than alkanes due to dipole-dipole forces
between C=O but however have lower temperatures than alcohols as alcohols have hydrogen
bonding.

Short chain aldehydes and ketones are soluble in water as they can form hydrogen bonds with water
molecules. However the solubility of aldehydes and ketones decreases with increasing chain lenghts
as the hydrocarbon part of the molecules becomes more significant so the hydrocarbon chain length
has more effect than the hydrogen bonding.

So the 3 Physical Properties of carbonyls are Smell, Boiling temperature, Solubility

Primary alcohol can be oxidised into aldehyde using a acidified potassium dichromate (VI) ions by
distillation while primary alcohol can be oxidised to carboxylic acid using same reagent but with
complete reflux. Primary alcohols can be oxidised from alcohols to aldehydes to carboxylic acids.
While secondary alcohol can be oxidised into ketones and cannot be oxidised to carboxylic acids as
ketones cannot be oxidised to carboxylic acids.

To reduce an aldehyde (or carboxylic acid) to a primary alcohol or a ketone to a secondary alcohol we
use the reducing agent LiAlH4 (Lithium Aluminium Hydride) dissolved in dry ether
Aldehydes can be oxidised to a Carboxylic acid using an Acidified potassium dichromate(VI) the more
common conventional way we would observe a color change for this oxidation from aldehyde to
carboxylic acid from ORANGE to GREEN solution we have an orange solution due to the +6 chromium
ions and a green solution due to the +3 chromium ions

Aldehydes can be oxidised to a Carboxylic acid using a Fehling’s solution we would see a color change
from deep blue solution to red precipitate (due to copper oxide which is red ppt)

Aldehydes can be oxidised to a Carboxylic acid using a Benedict’s solution we would see a color
change from deep blue solution to red precipitate (due to copper oxide which is red ppt)

Fehling’s solution and Benedict’s solution are same

(Blue to Red) NOTE THAT THESE TWO SOLUTIONS
DON’T ACTUALLY OXIDISE ALCOHOLS TO ALDEHYDES
THEY ARE SIMPLY JUST USED FOR DISTINGUISHING
ALDEHYDES FROM KETONES
Aldehydes can be oxidised to a Carboxylic acid using a Tollen’s reagent we would see a color change
from colourless solution to silver mirror
There are 4 oxidising agents to oxidies aldehyde (from primary alcohol) to carboxylic acid: using
acidfied potassium dichromate (VI), using benedict solution, Fehlings solution and Tollens reagent

The bendict and fehlings solution both show a color change form deep blue solution to a red
solution for the oxidiation of aldehydes to carboxylic acids and not show any color change remain
deep blue solution in the presence of a ketone (which cannot be oxidised into carboxylic acid it can be
however it is very difficult).

A Tollens solution shows that a colorless solution into a silver mirror solution
The iodine with Sodium Hydroxide (alkaline) test is a test for
Methyl Ketones which will give us a Sodium Carboxylate and
CHI3 (yellow ppt)
We can also using the Iodoform test to identify the presense of a CH3CO group which is found in
ethanal and all methyl ketones. REMEMEBER that this group of CH3CO for iodoform testing can be
found in Ethanal (2 carbon aldehyde group) as well as in methyl ketones (where the carbonyl group is
in the second carbon).

This Iodoform reaction takes place by adding the carbonyl compound to an Alkaline solution (NaOH)
of iodine, warmed and cooled to form CHI3 which is a yellow insoluble precipitate.

The test is also a positive test for secondary alcohols like propan-2-ol or butan-2-ol. So this is not the
most reliable test
The group being tested by the iodoform test is the CH3CO-

Compound containing Methyl Ketone + I2 (in NaOH) ---> Carboxylate salt + CHI3
IODOFORM test used to split carbon compounds.

The products of the iodoform test are:

2-hydroxy butanenitrile the (2-hydroxy shows us where the
OH group lies in the carbon compound). The Nitrogen bonded
with the Carbon shows that the compound is a nitrile (due to
the bonding of the compound with Nitrogen)

This is an AMIDE which is any compound that is R-NH2 where

a Nitrogen and Hydrogen are bonded is called Amide.

This is called a NITRILE which is basically any compound that is

R-CN where a Carbon and Nitrogen are bonded calling that
Nitrile.

When naming these products from nucleophilic addition with HCN we call them first by the OH group
the (hydroxy group) and then by the CN (nitrile group). So these products from the nucleophilic
We call these
addition with HCN add Hydrogen and Cynide to the aldehydes and ketones.
reactions the nucleophilic addition of Carbonyl groups (such
as aldehydes and ketones) with HCN (hydrogen cyanide) the
product formed from such carbonyl nucleophilic additions are
hydroxy nitriles

The nucleophilic addition of HCN (hydrogen cyanide) is a regenerative Cynide ion process. It is a 2 step
mechanism. And forms the hydronitrile products

Nueclophilic addition with Hydrogen Cyanide. So Hydrogen Cyanide will react with the carbocation of
the carbonyl to form an infinitely reocuring Cynaide nucleophile, regeneration.
BETTER VERSION OF HYDROGEN CYANIDE REACTION WITH KETONE
Optical activity can be used as evidence for this nucleophilic addition with Hydrogen Cynide to
carbonyl compounds. This is because the carbonyl compounds are planar so there are equal chance of
attack from each side of the plane. The products contains a chiral centre and a racemic mixture as
there are equal amounts of enantiomers that are non-superimposible mirror images of each others.
There are equal chance of attack so we find that we form equal amounts of both enantiomers. So we
form a racemix mixture so the product has no optical activity. This concept is similar to the SN1 (2
step) secondary/tertiary alcohol nucleophilic substitution but instead this is not an alcohol and
instead a carbonyl compound and a nucleophilic addition reaction with Hydrogen Cyanide.

The brady’s reagent also known as 2,4-DNPH can be used as a test for the presence of a carbonyl
compound. If there is any carbonyl compound (aldehyde or ketone) then we should see a color
change to form an Orange Precipite
The Sodium Carbonate solution reacts with the acid to form carbon dioxide effervescence
Bendict (fehlings solution) blue to red
2,4 DNPH or bradys solutions forms orange ppt in the presence of carbonyl compounds
Brady’s reagent 2,4-DNPH is used to test for carbonyl compounds and it will give a positive of orange
precipitate.
Aldehyde to primary alcohol or Ketones to secondary alcohols are reduced using a LiAlH4 reagent
dissolved in dry ether.

In the iodoform test. We add iodine solution with Sodium Hydroxide to give off CHI3 + HCOONa
The iodoform test is used to test for the presence of CH3CO group which is found in Ethanal and
Methyl Ketone. This test would take place by adding Iodine with dissolved Sodium Hydroxide solution.

In this reaction the ETHANAL with CH3CHO into CHI3 (replacing all the hydrogens from the methyl)
giving a yellow precipitate and HCOONa (carboxylate salt)
Practice this Carbonyls such as aldehydes and ketones can do a nucleophilic addition reaction with
Hydrogen Cyanide. For ethanal nucleophilic addition with HCN
We can form racemic mixtures this is because the aldehyde always has a planar carbonyl group, and
because of this planar structure of the carbonyl the CN ion can be attacked equally from either side.
A carboxyl functional group is a carbonyl with a hydroxyl group attached to the same carbon
A carboxylic acid has strong dipole-dipole forces, hydrogen bonding and london forces in the carbon
chain.
Also the boiling temperature increases with increased molar mass as the number of carbon chains
increases, this causes the London Forces to increase. Which thus increase the boiling points.
The solubility of the carboxylic acids is a lot more than with aldehydes/ketones this is because the
carboxylic acid has both strong hydrogen bonding O-H and PD-PD C=O bonding. So there can be two
different ways of hydrogen bonding with the carboxylic acid which causes the solubility of carboxylic
acids to be far greater than carbonyl groups. However as the chain length increases the London
Forces become more dominated so there will not be any effect from the PD-PD bonding or Hydrogen
Bonding.

We can form a carboxylic acid with a primary alcohol or aldehyde. This reaction is carried out under
reflux with an oxidising agent of acified potassium dichormate (VI) with concentrated sulfuric acid.
The reaction is carried out under reflux, the condenser is vertical so the vapour goes up and condense.
And for an aldehyde we would need to do it under a distillation so there is not complete oxidation of
alcohol.
Heat Under Reflux

Cyanide: CN

Carboxylic acids can be formed from the hydrolysis of nitriles (Cyanide). A nitrile is an organic
compound that contains C(triple bond)N. We can either react the Nitrile compound with an ACID
which is a 1 step process. Or react the Nitrile compound with an ALKALINE which is a 2 step process.
And in the 1 step of alkaline hydrolysis we would form a carboxylate ion and later with further react
with an acid form a carboxylic acid.
There are 4 main reactions of carboxylic acids

When Alcohols or any other compound reacts with Phosphoric Acid it gives a dehydration reaction.
Alcohols to Alkene
This is the first reaction with carboxylic acids this is the reduction reaction where carboxylic acids can
be transformed into primary alcohols using a reducing agent which is LiAlH4 dissolved in dry ether.
Aldehydes cannot be formed from the reduction of carboxylic acid into primary
alcohol as aldehydes are easily reduced, so when we reduce the carboxylic acid into primary
alcohol we would then need to oxidised the primary alcohol to turn it into an aldehyde. So to reduce a
carboxylic acid to aldehyde it is 2 step reaction.
The second reaction of carboxylic acids is neutralisation reaction. This takes place between a STRONG
acid NaOH (sodium hydroxide) with weak acid (organic carboxylic acid). The product formed from this
neutralisation between carboxylic acid is Sodium carboxylate (or a carboxylate salt) + water. A
carboxylate is a CH3COO^- ion. So a sodium carboxylate is CH3COONa As Na is + Na^+ and CH3COO^-

ADD EXCESS HCl to go from Carboxylate salt to Carboxylic acid

The third reaction of carboxylic acids is halogenation. Like the halogenation reaction with alcohol.
Where alcohol reacts with ROH + PCl5 it forms HCl + POCl3 + RCl.
A carboxylic acid will also have a halogenation reaction where: RCOOH reacts with PCl5 and form
same two products HCl + POCl3 and RCOCl
The OH disappears, in halogenation with PCl5 with alcohol and carboxylic acids

The fourth reaction with carboxylic acids is esterfication between carboxylic acids and alcohols. The
OH group would be removed from the carboxylic acid and the H (hydrogen) would be lost from the
alcohol. To form an ester and water. Esters have a distinctive smell as they smell like perfumes
First part of the name of the ester comes from the alcohol and second part comes from the acid

Acidified potassium dichromate(VI) when only oxidises primary alcohol to aldehyde to carboxylic acid,
while secondary alcohol oxidises to ketone.
Carboxylic acid (RCOOH) reacts with PCl5 ---> HCl + POCl3 + RCOCl (this forms an acyl chloride) and
not a chlorobutane.The butyl methanoate is an ester
Butanenitrile when this reacts with hydrochloric acid hydrolysis:
CH3CH2CH2CN + H2O + H^+ ----> CH3CH2CH2COOH + NH4^+
(NOTE remember a nitrile when there is acid hydrolysis or alkaline hydrolysis it will form a carboxylic
acid)
The carboxylic acid loses the OH group while the alcohol loses the H
The conditions for the esterfication of a carboxylic acid we add an alcohol in concentrated Sulfuric
Acid. And the conditions for the reduction of carboxylic acid to alcohol we use LiAlH4 in dissolved dry
ether.

We first need to reduce our carboxylic acid to alcohol and then oxidise the alcohol to aldehyde this is
because the aldehyde is more easily reduced than carboxylic acid.
THIS IS ALL YOU NEED TO KNOW ABOUT AMIDES!!!

Acyl chlorides are formed from the halogenation of carboxylic acids.

RCOOH + PCl5 ---> HCl + POCl3 + RCOCl
So this RCOCl is what becomes the acyl chloride, an acyl chloride is basically when the OH group from
the carboxylic acid is replaced by the Chlorine
In naming acyl chlorides we first name the main chain branch and then the halogen
Because acyl chlorides have a functional group of RCOCl instead of (RCOOH which is carboxylic acid,
these acyl chlorides are produced from halogenation of carboxylic acids, removing the OH group)
These COCl acyl chloride group as it is surrounded by two highly electronegative atoms the Carbon
atom can be readily attacked by nucleophiles.

The first reaction with acyl chlorides (RCOCl) we can react acyl chlorides with water to form a
carboxylic acid and misty fumes form Hydrogen Chloride.
The second reaction is where we can also make esters from reacting acyl chlorides with Alcohols and
this time around unlike alcohol and carboxylic acid esterfication reaction which is an equalibirum
reaction meaning that it is an incomplete reaction. The esterfication reaction between Acyl Chlorides
(RCOCl fromed from halogenation of carboxylic acids) and alcohols form a complete reaction, not an
equalibirum reaction, however the problem with using acyl chrlodies for making esters is that
Hydrogen Chloride is formed which gives of misty fumes, which are toxic.

R-C=O-NH2 this is an amide (NH2 nitrogen with

hydrogen) a nitrile is CN

Amide is when R is bonded with Carbon double bond

Oxygen and NH2
The third reaction is where acyl chlorides react with concentrated ammonia gas which forms an
amide (which has a RCONH2 functional group an AMIDE group is basically a carboxylic acid with a NH2
attached to it) and Hydrogen Chloride gas. And because ammonia which is an alkaline gas and
Hydrogen Chloride (misty fumes) which is an acidic gas can undergo a further side reaction where
Ammonia and Hydrogen Chloride react to form Ammonium Chloride NH4Cl

Fourth reaction is when Acyl Chlorides react with Primary Amines (RNH2 simply a carbon chain
attached to NH2 not like amide where it is basically a carboxylic acid attached by NH2). In this
reaction we will form an N-subsituted amide and like all other reactions a Hydrogen Chloride gas (HCl)
We call such an N-subsituted amide N-methylethanamide
Secondary Amines are basically N group attached to two carbon methyl groups while Primary Amines
are N group attached to 1 carbon methyl group. Like with all acyl chlorides when Secondary Amines
react with a Secondary Amine it forms a N,N dimethylethanamide (amide is when RCONH2 Or
RCOCH3CH3) the two Ns at the beginning shows where the two methyls are attached to similar to
2,2-dimethylethanamide. REMEMBER HOW AMIDES ARE NAMED.
Amides ---> RCONH2 or RCOCH3CH3
Primary Amine ---> RNH2 example when 2 hydrogen atoms are bonded to 1 Nitrogen atom
Secondary Amine ---> HNRR example when two methyl groups are attached to 1 Nitrogen atom
bonded with Hydrogen

Esters can be formed when either Carboxylic acids react with Alcohols under CONCENTRATED Sulfuric
Acid catalyst OR when Acyl Chlorides react with Alcohols under CONCENTRATED Sulfuric Acid catalyst
To name an ester we first need to know how it is made basically the OH group is lost from the
Carboxylic Acid and the Hydrogen atom is lost from the Alcohol. NOW that we know this we also need
to understand that when naming the ester the first bit of the ester comes from the Alcohol and the
Second part from the Carboxylic Acid.
So [HCO][OCH2CH3] can be named as, [ ] shows the spliting of alcohol and carboxylic acid. Alcohol
first name is Ethanol and Carboxylic Acid second name is Ethanoic Acid. So the name of ester is Ethyl
Methanoate.

Naming of ESTERS is Alcohol first & Carboxylic Acids second

Esters are insoluble in water as none of the hydrogen atoms are bonded to any electronegative atoms
so there is no hydrogen bonding that is experienced by the ester.

There is a very important reaction you need to know off for ESTERS these are the HYDROLYSIS
reactions between Esters. Hydrolysis is done to reverse the process of esterification. So when water
and ester in either ACIDIC or ALKALINE conditions react they reverse the process of esterfication. This
Acidic and Alkaline hydrolysis is similar to when Nitriles hydrolyse to form Carboxylic acids, and
release NH4+ or NH3 depending on hydrolysis conditions.
Acidic hydrolysis is basically the reverse reaction for esterfication reaction. If we remember that when
Carboxylic Acid and Alcohol react they form esters and water and the catalyst is Sulfuric acid. So
ACIDIC hydrolysis of an ester is essentially just the opposite reaction, this is why we say that this
esterfication reaction is at equilibrium.

Water is bascially consists of H+ OH- ions so basically water can act also as an acid

However in the Alkaline Hydrolysis of esters we form a Carboxylate Salt and Alcohol a Carboxylate is a
RCOO^- and a salt is usually Sodium so Na^+. So Carboxylate Salt is RCOONa. And we need to further
reacti it with by addition of ACID this reaction is similar to that of Nitrile (RNH3) Alkaline Hydrolysis.
This reaction is better as it is a complete reaction and has better yeild of Carboxylic Acid.
Esterfication Catalyst is Sulfuric Acid (an acid)

Hydrolysis of Esters
Acidic: When we add an Acid it speeds of reaction of
desterfication
Alkaline: We have to add Alkaline to react with ester and then
later add Acid to react with the carboxylate ion to form
Carboxylic Acid

Remember Nitrile hydrolysis forms Carboxylic acids + NH4+ or NH3

Esters can also be hydrolysed to break polyester to monomers. By either Acidic conditions H2O with
reactant catalyst Acid. Or by Alkaline conditions NaOH reacts with Ester to form RCOO- Na+ + ROH
fruther reactions with Acid H+ gives us RCOO- + H+ ---> RCOOH
Saponification is a process of Alkaline Hydrolysis of Esters
Many alcohol and carboxylic acid monomers that react together to form multiple esters. The alcohol
is usually called a diole and the carboxylic acid with two groups is called the dicarboxylic acid
Polyesters could also be made using a diacyl chlorides (basically when two acyl chlorides groups are
joined together by a benzene ring) instead of dicarboxylic acid. However this is not very useful as the
reaction forms Hydrogen Chloride which is a hazardous gas.
ADDITION POLYMERISATION (long repeating chain only)
Many monomers can join together to form a bigger chain polymer
CONDENSATION POLYMERISATION (water formation)

When you are making a Polyester. The repeating monomer units are only repeated once as showen
above.
Ethanamide can be formed when Ethanoyl Chloride (an acyl chloride RCOCl) reacts with Ammonia
(NH3): RCOCl + NH3 ---> RCONH2 + HCl

Polyesters are formed by either: diol + dicarboxylic acid OR diol + diacyl chloride

WHENEVER WE HAVE A TRIESTER the answer to the alcohol produced is Propane-1,2,3-triol

The advantage of forming esters from acyl chlorides over carboxylic acids is that the reaction goes to
completion while the esterfication using carboxylic acids are in equialibrium point. Also the
disadvantage of using acyl chloride is that HCl gas is formed which is toxic.

An ester methyl propanoate is formed when propanoic acid and methanol acid react together and
form water plus ester
The hydrolysis using alkaline for ester Ethyl Ethanoate is used to split the ester into ALCOHOL and
CARBOXYLIC ACID so it is a reverse esterfication reaction. We can get this as an ethanoate is formed
(AKA a carboxylate RCOO^- salt Na^+) and upon further acidification of the Sodium Ethanoate
(carboxylate) we can form the carboxylic acid and alcohol in a complete reaction not equilibrium like
that when hydrolysis occurs in acidic conditions.

Alkaline used up so is not a catalyst

Chromatography is used to separate a mixture into its individual components and identify the
components by the distance they travelled up the paper. Used to determine the purity.
Stationary phase when liquid or solid does not move. A mobile phase when liquid that moves through
the stationary phase and transports the compounds.

lower affinity for this mobile phase due to only there being London dispersion forces. So will reach a
lower height. As there will be weaker attraction between polar and non-polar substances so the
distance travelled upwards is smaller. Polar like Polar and Non-polar like Non-polar, in terms of
attraction
Simple chromatography is used with Paper chromatography and TLC (thin-layer chromatography).
Paper chromatography: stationary phase is the water trapped in the fibers of the chromatography
paper, the mobile phase is the solvent.
TLC is when instead of paper the stationary phase is a sheet of glass coated with silica or alumina.
The Rf values are only for paper and TLC chromatography (TLC the stationary phase is with a sheet of
glass coated with silica or alumina)
More attacted to stationary phase meaning that the liquid is more likely to not move. While a liquid
that is more attracted to mobile phase is more likely to move.

We need to use molecular masses accurate to 4 decimal places

Just looking at it in more accuracy tells the compounds apart
High performance liquid chromatography: unlike Column Chromatography is not separated by gravity
but instead is separated by high pressure through a tube. The stationary phase is silica and mobile
phase is hexane. The stationary phase is much smaller so better seperation of components.
These seperated components are detected using their absorption of UV radiation and results are
analysed on a computer.

The stationary phase is usually a polar substance, and the mobile phase is a non-polar substance
Gas chromatography is done in an oven to vaporise the gasses
The gas substance used here must be a volatile substance (volatility is the ability of a substance to be
vaporised) so a non-volatile substance does not vaporise easily.
Gas Chromatography is used to essentially measure the amount of each seperated component in a
mixture.
Gas Chromatography takes place in an oven, the substances are vaporised. And there must be volatile
substance used (substances that can easily be vaporised). And it is used to seperatre a mixture into
gases and measure the amount of each component in a mixture of volatile substance.
As the stationary phase is polar so the mobile phase should also be polar as polar-polar substances
attract each other the best hence the retention time is longer, due to this polar polar attraction.

In gas chromotography the stationary phase should be liquid or solid, and the mobile phase should be
an inert gas.

The compounds in chromatography are seperated due to the difference between a mobile phase and
stationary phase. This is because of the attraction to mobile and stationary phases.
In Gas Chromatography:
Stationary phase --> liquid/solid
Mobile phase --> inert gas

In HPLC:
Stationary phase --> solid silica (non-polar)
Mobile phase --> hexane (polar) or any other Solvent
There are two main types of NMR spectroscopy these are: Carbon-13 NMR and proton NMR.
The y-axis is called absorption and the x-axis is called chemical shift

The solvent used in NMR spectroscopy is the CDCl3. WHERE the D stands for deuterium which is a
heacy isotope of Hydrogen. So then this solvent does not interfere with molecules containing carbon
and hydrogen.
TMS is the standard that all other hydrogens and carbons are measured against. It is chemically
unreactive so will not react with the sample. In a sample all signals for carbons or hydrogens give
characteristic chemical shift from 0ppm.

Carbon 13 NMR spectroscopy tells us the chemical shifts of the chemical. The number of vertical lines
tells you the number of different chemical enviroments in the molecule. Position of vertical lines tells
you the chemical shift of each carbon atom. It also allows you to deduce the chemical environments.
Propan-1-ol has 3 carbon enviroments so there must be 3 vertical peaks with corresponding chemical
shifts. The chemical shift between 80 and 60 is carbon enviroment C. This is because carbon
enviroment C is connected to an OH group so the chemical shift is 80-60. Carbon enviroments B and A
are between 30 and 0. This is because their chemical shifts are that of alkanes, so they are in those
ranges. HOWEVER because Carbon enviroment B also is attached to carbon that is connected with OH
group thus the chemical shift is closer to the chemical shift at Carbon enviroment C, while carbon
enviroment A is just an alkane.
Ratio is 1:1:1

A carbon environment has 2 carbon environments thus they have twice the absorption/peak. While B
carbon environment has only 1 carbon peak. And as carbon environment B is connected to OH group
it has a chemical shift above 60.
Ratio is 1:2

The carbon enviroment A means that the compound has a carbonyl group as it has a peak absorption.
So automatically we can say that yes this compound is an aldehyde CH3-CH2-CHO so carbon
enviroment A is at 210-200 chemical shift. And chemical shift between 40-30 is cabron enviroment B
which is closer to the carbon with the carbonyl group attached to carbon. And C is the carbon which is
furthest away from the carbon attached to carbonyl group attached. AND this compound has 3
vertical peak of all different carbon environments.
Ratio is 1:1:1

The chemical shift peaks at those groups that are attached to carbons. So CH3 the cabron the atoms
attached to this cabron are only 3 Hydrogens. NOTE that CH3-CH2 the C-H bond does not have a
chemical shift peak we only consider the C-C chemical shift at this instance however if we had CH3-
COOH we would only consider the C-C and not the C-COOH. This is because this would be its very own
chemical environment, the COOH, O=C-O so there will be a chemical shift here and not in the
chemical environment C-COOH as only C-C present here.

The NMR spectra has a CDCl3 dissolved. TMS is a reference standard with a NMR spectra at chemical
shift 0.
In Proton NMR Spectroscopy the number of vertical lines tells us the number of different chemical
environments in the molecules. AND BY INTEGRATIONS THE AREA UNDER THE PEAK represents the
relative number of hydrogen atoms in each environment.

The integration trace helps us identify the number of hydrogen atoms present in each environment.
This is how we use the sepectra
The chemical shift peak areas tells us the number of hydrogen (protons) atoms in that very distinct
hydrogen environment. There are also 4 hydrogen environments as there are 4 vertical peaks. D
environment as it only has 1 peak area means that it has 1 carbon atom in its environment. A
environment has 3 peak area so it must be A where there are 3 C-H. AND C and B both have same
peak areas showing they both have same hydrogen atoms attached to carbon. And because C is closer
to O=C-H so its chemical shift is closer to that of environment D.

In this case there are 3 peaks thus showing that there are 3 hydrogen environments. And because B
environment has 2 peak area it must be B. Also because proton environment has 3 peak area in C and
A. To distinguish which one is where, we can see that C proton environment is attached to a C=O
functional group even though it is not connected to any protons the fact that it is present with C
proton environment means that it will have a slightly higher chemical shift. THUS C is further than A
even though they both are the same with 3 C-H bonds, the closer C=O functional group influences the
chemical shift.
d proton NMR spectroscopy is O-H so the proton
is bonded with the oxygen for there to be a
proton NMR peak which is singlet as the
corresponding carbon to the Proton Environment
has no Carbon attached to any Hydrogen so no
spiting of peaks

Remember that the higher resolution splitting is

from how many Hydrogen atoms are to the
corresponding Carbon atom of the Proton
Environment. Proton environment could also be
O-H without any Carbon being bonded to it.
Splitting patterns are caused as the neighbouring Hydrogen (protons) interfere with the protons

So the number of protons on the adjacent carbon TELLS

US THE NUMBER OF SUB-PEAKS
ALSO REMEMBER a QUINTET is when there are 5 SUB PEAKS

Our peaks at A or B or C will still remain the same however in a high resolution proton NMR
spectroscopy we will see further peaks. And these further peaks depend on the number of adjacent
protons on each proton environment.
A proton environment is a triplet as it has 2 adjacent protons to the carbon-hydrogen (C-H) so it is a
triplet. B proton environment is a quartet as it has 3 adjacent protons to the carbon-hydrogen (C-H),
and C proton environment is a singlet as it has no adjacent protons to the carbon-hydrogen (C-H)
So A is a quartet so there must be 3 hydrogen's in its adjacent Carbon Hydrogen (C-H) bond, also it
has a peak area of 2 so as the integration of proton NMR spectra tells us the number of protons in the
hydrogen(proton) environment so the environment of hydrogen has a carbon bond with 2 hydrogen's,
hence it proton environment is CH2. The chemical shift is 4.1 so it is either an alcohol or an ester
bonded next to the CH2. Also in proton environment B it is a singlet so there are no hydrogen's
attached to the adjacent carbon bond, and the proton environment has 3 hydrogen atoms as the
peak area of it is 3. The chemical shift is 2 so the CH3 is bonded with a C=O (ester) as it has no
hydrogen's adjacent it. Hydrogen environment C is triplet so it has 2 hydrogen's attached adjacent to
it, and the peak area is 3 so there are 3 hydrogen's in the hydrogen environment. So it is CH3, also the
chemical shift indicates that next to it is a CH2. So final compound from chemical shift is:
CH3-CO-O-CH2-CH3
b a c

We first identify that there are 5 Proton Environments. OH groups are also singlet this is because it
must be a C-H that is connected to another Carbon with Hydrogen's attached to it, however there are
no carbons and is only a OH so there is no adjacent carbon attached to any hydrogen(proton) thus it
will always remain a singlet. A environment is attached just to 1 carbon with 2 hydrogen’s so it is a
triplet and this is the same with C environment. However with B environment there are 2 carbons
both attached to 2 protons thus it is a quintet (5 sub peaks) dues to there being 4 hydrogen's adjacent
to carbons.
A quintet is when there are 5 hydrogen’s adjacent to the carbon

There are 3 hydrogen environments.

A proton environment has a peak area of 3 as that is the number of hydrogen’s on the carbon. And on
the adjacent carbon there are only 2 hydrogen's so it has a triplet sub-peaks.
B proton environment has a peak area of 2 as that is the number of hydrogen’s on the carbon. And on
the adjacent 2 carbons there are 4 hydrogen’s so it is a quintet with 5 sub-peaks.
C proton environment has a peak area of 1 as that is the number of hydrogen’s on the carbon. And on
the adjacent carbon there are 2 hydrogen’s so it will form a triplet with 3 sub-peaks.

A compound can have only 1 peak as all the protons are in the same environment
An explanation for one splitting pattern: B hydrogen environment is a quartet because there are 3
protons on the adjacent carbon. And due to n+1 rule (3+1=4) there will be a quartet fragmentation, so
4 subpeaks, at a peak area of 3.

There are 3 proton environments that are the same so they are equal to 1 peak for C-C spectra peak.
Peak area of 3, with no hydrogens attached to their adjacent carbons. Also the other peak is O-H
sepectra, there are 0 hydrogens attached to adjacent carbon.