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IGCSE Chemistry Edexcel 

4. Organic Chemistry

CONTENTS
4.1 Introduction
4.1.1 Organic Compounds
4.1.2 Naming Organic Compounds
4.1.3 Classifying Organic Reactions
4.2 Crude Oil
4.2.1 Crude Oil & Fractional Distillation
4.2.2 Combustion
4.2.3 Nitrogen Oxides & Sulfur Dioxide
4.2.4 Cracking
4.3 Alkanes
4.3.1 Alkanes
4.3.2 Halogens & Alkanes
4.4 Alkenes
4.4.1 Alkenes
4.4.2 Bromine & Alkenes
4.5 Alcohols
4.5.1 Alcohols
4.5.2 Oxidation of Ethanol
4.5.3 Manufacture of Ethanol
4.6 Carboxylic acids
4.6.1 Carboxylic Acids
4.6.2 Reactions of Carboxylic Acids
4.7 Esters
4.7.1 Esters
4.7.2 Practical: Preparation of Ethyl Ethanoate
4.8 Synthetic polymers
4.8.1 Addition Polymers
4.8.2 Disposal of Addition Polymers
4.8.3 Condensation Polymers

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4.1 Introduction YOUR NOTES


4.1.1 Organic Compounds
Representing Organic Compounds
Introduction
Organic Chemistry is the scientific study of the structure, properties, and reactions
of organic compounds. Organic compounds are those which contain carbon
For conventional reasons metal carbonates, carbon dioxide and carbon monoxide
are not included in organic compounds
Definition of a Hydrocarbon
A compound that contains only hydrogen and carbon atoms
Representing Organic Molecules
Organic compounds can be represented in a number of ways:
Empirical Formulae
Molecular Formulae
General Formulae
Structural Formulae
Condensed Structural Formulae

The empirical formula shows the simplest possible ratio of the atoms in a
molecule
For example: Hydrogen peroxide is H2O2 but the empirical formula is HO
The molecular formula shows the actual number of atoms in a molecule
For example:

The general formula shows a ratio of atoms in a family of compounds in terms of

'n' where n is a varying whole number
For example, the general formula of a molecule that belong to the alkane
family is CnH2n+2

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The displayed formula shows the spatial arrangement of all the atoms and bonds YOUR NOTES
in a molecule 
This is also known as the graphical formula.
For example:

In a structural formulae enough information is shown to make the structure clear,

but most of the actual covalent bonds are omitted
Only important bonds are always shown, such as double and triple bonds
Identical groups can be bracketed together
Side groups are also shown using brackets
Straight chain alkanes are shown as follows:

 Exam Tip
For defining a hydrocarbon, you must specify that they are compounds
which contain hydrogen and carbon atoms only, no other element is
present.You may not be asked to name branched chain organic compounds
but you will come across them. It is useful to know that the numbers in the
names of these compounds refer to the position of the side chains with
respect to the main chain.

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Organic Terminology YOUR NOTES

Three important terms to know in this topic are homologous series, functional 
group and isomerism

Homologous Series
This is a series or family of organic compounds that have similar features and
chemical properties due to them having the same functional group
All members of a homologous series have:
The same general formula
Same functional group
Similar chemical properties
Gradation in their physical properties
The difference in the molecular formula between one member and the next is
CH2
Functional Group
Functional group: A group of atoms bonded in a specific arrangement that
influences the properties of the homologous series
Some examples are shown here
Structures and Names of Common Functional Groups

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

Isomerism
Isomers are compounds that have the same molecular formula but different
displayed formulae
Eg. propene and cyclopropane

Isomers of C3H6 show the same molecular formula but different structures. Isomers
can show similar physical and chemical properties or if they have different functional
groups, the properties can be different.

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4.1.2 Naming Organic Compounds YOUR NOTES


Naming Organic Compounds
Names of compounds
The names of organic compounds have two parts: the prefix or stem and the end
part (or suffix)
The prefix tells you how many carbon atoms are present in the longest continuous
chain in the compound
The suffix tells you what functional group is on the compound
Examples of Naming Organic Molecules

Further rules for naming compounds

When there is more than one carbon atom where a functional group can be located
it is important to distinguish exactly which carbon the functional group is on
Each carbon is numbered and these numbers are used to describe where the
functional group is
When 2 functional groups are present di- is used as a prefix to the second part of
the name

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YOUR NOTES


Isomers can be distinguished by following the naming rules

 Exam Tip
You may not be asked to name branched chain organic compounds but you
will come across them. It is useful to know that the numbers in the names of
these compounds refer to the position of the side chains with respect to the
main chain.

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4.1.3 Classifying Organic Reactions YOUR NOTES


Classifying Organic Reactions
The reactions of organic compounds can be classified into substitution, addition
and combustion
Substitution
A substitution reaction takes place when one functional group is replaced by
another
Example: Methane reacts with bromine under ultraviolet light

CH4 + Br2 → CH3Br + HBr

Methane + Bromine → Bromomethane + Hydrogen Bromide

Addition
An addition reaction takes place when two or more molecules combine to form a
larger molecule with no other products
Example: Bromine will react with ethene and the bromine molecule will react and
add across the double bond of the ethene
C2H4 + Br2 → C2H4Br2

Ethene + Bromine → Dibromoethane

Combustion
This is the scientific term for burning. In a combustion reaction, an organic
substance reacts with oxygen to form carbon dioxide (or carbon monoxide if
incomplete combustion) and water.
Example: Alkenes burn when heated in air of oxygen
If there is an unlimited supply of air / oxygen, the products are carbon dioxide
and water:
CH4 + 2O2 → CO2 + 2H2O

C 3H8 + 5O 2 → 3CO 2 + 4H2O

This is termed complete combustion

If there is a limited supply of air / oxygen, the products are carbon monoxide and
water:
CH4 + ½O2 → CO + 2H2O

This is termed incomplete combustion

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4.2 Crude Oil YOUR NOTES


4.2.1 Crude Oil & Fractional Distillation
Crude Oil & Fractional Distillation
Crude oil as a mixture is not a very useful substance but the different
hydrocarbons that make up the mixture, called fractions, are enormously valuable,
with each fraction having many different applications
Each fraction consists of groups of hydrocarbons of similar chain lengths
The fractions in petroleum are separated from each other in a process called
fractional distillation
The molecules in each fraction have similar properties and boiling points, which
depend on the number of carbon atoms in the chain
The size and length of each hydrocarbon molecule determines in which fraction it
will be separated into
The size of each molecule is directly related to how many carbon and hydrogen
atoms the molecule contains
Most fractions contain mainly alkanes, which are compounds of carbon and
hydrogen with only single bonds between them

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Diagram showing the process of fractional distillation to separate crude oil in a YOUR NOTES
fractionating column

Fractional distillation is carried out in a fractionating column which is very hot at
the bottom and cool at the top
Crude oil enters the fractionating column and is heated so vapours rise
Vapours of hydrocarbons with very high boiling points will immediately condense
into liquid at the higher temperatures lower down and are tapped off at the bottom
of the column
Vapours of hydrocarbons with low boiling points will rise up the column and
condense at the top to be tapped off
The different fractions condense at different heights according to their boiling
points and are tapped off as liquids
The fractions containing smaller hydrocarbons are collected at the top of the
fractionating column as gases
The fractions containing bigger hydrocarbons are collected at the lower sections
of the fractionating column

 Exam Tip
As you move up a fractionating column the temperature decreases, so the
compounds with higher boiling points come off lower down the column.

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The Main Fractions YOUR NOTES

Properties of the main fractions of crude oil 
Viscosity: This refers to the ease of flow of a liquid. High viscosity liquids are thick
and flow less easily. If the number of carbon atoms increases, the attraction
between the hydrocarbon molecules also increases which results in the liquid
becoming more viscous with the increasing length of the hydrocarbon chain. The
liquid flows less easily with increasing molecular mass
Colour: As carbon chain length increases the colour of the liquid gets darker as it
gets thicker and more viscous
Melting point/boiling point: As the molecules get larger, the intermolecular
attraction becomes greater. So more heat is needed to separate the molecules.
With increasing molecular size there is an increase in boiling point
Volatility: Volatility refers to the tendency of a substance to vaporise. With
increasing molecular size hydrocarbon liquids become less volatile. This is
because the attraction between the molecules increases with increasing molecular
size
Trend in Boiling Point of the Main Fractions

Uses of the different fractions obtained from petroleum (crude oil)

The petrochemical industry is hugely important for modern society and
development
The fuels that are used in most modern methods of transport (cars, trains,
airplanes etc.) are all based on oil products
Polymers, lubricants, solvents, detergents and adhesives are all products that are
obtained from crude oil

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The array of fractions in crude oil and the huge range of compounds we can YOUR NOTES
produce from them all stem from carbon’s ability to form multiple strong covalent 
bonds with itself leading a huge number of organic compounds
The main fractions and their uses are described in the following table:
Uses of Crude Oil Fractions

 Exam Tip
You need to learn the names and uses of the main fractions obtained from
crude oil: refinery gases(also known as liquid petroleum gases), gasoline,
kerosene, diesel, fuel oil and bitumen. Gasoline and petrol are the same
thing; gasoline is the term used in the USA.

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4.2.2 Combustion YOUR NOTES


Fuels & Combustion
The combustion of fossil fuels is the major source of atmospheric pollution
Fossil fuels include: coal, oil, natural gas, oil shales and tar sands
Non-renewable fossil fuels are obtained from crude oil by fractional distillation
Petrol is used as a fuel in cars, kerosene is used to fuel aircraft and diesel oil is
used as a fuel in some cars, trucks and heavy vehicles such as tanks and trains
Coal is used in power stations and also steel production
Natural gas consists mainly of methane, CH4
There are finite amounts of fossil fuels and they all contribute to
pollution and global warming
All these fuels contain carbon, hydrogen and small quantities of sulfur
Combustion Products
The burning of fossil fuels releases the gases carbon dioxide, carbon monoxide,
oxides of nitrogen and oxides of sulfur
In addition incomplete combustion of the fuels gives rise to unburned
hydrocarbons and carbon particulates

Complete versus Incomplete Combustion

A fuel is a substance which releases energy in an exothermic reaction
When the fuel is a hydrocarbon then water and carbon dioxide are the products
formed
Hydrocarbon compounds undergo complete and incomplete combustion
Complete combustion occurs when there is excess oxygen
For example, the combustion equation for propane is:
C3H8 + 5O2 → 3CO2 + 4H2O

Incomplete Combustion
Incomplete combustion occurs when there is insufficient oxygen to burn
It occurs in some appliances such as boilers and stoves as well as in internal
combustion engines
The products of these reactions are unburnt fuel (soot), carbon monoxide and
water
Methane for example undergoes incomplete combustion in an oxygen-poor
environment:
2CH4 + 3O2→ 2CO + 4H2O

CH4 + O 2→ C + 2H2O

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YOUR NOTES
 Exam Tip
You don't need to learn these equations, but you do need to be able to 
predict the products of combustion given the composition of the fuel and
the conditions.

Dangers of Carbon Monoxide

Carbon monoxide is a toxic and odourless gas which can cause dizziness, loss of
consciousness and eventually death
The CO binds well to haemoglobin which therefore cannot bind oxygen and
carbon dioxide
Oxygen is transported to organs
Carbon dioxide is removed as waste material from organs

The high affinity of CO to haemoglobin prevents it from binding to O2 and CO2

 Exam Tip
Though CO2 is not a toxic gas, it is still a pollutant causing global
warming and climate change.

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4.2.3 Nitrogen Oxides & Sulfur Dioxide YOUR NOTES


Formation of Nitrogen Oxides
Nitrogen Oxides
These compounds (NO and NO2) are formed when nitrogen and oxygen react in the
high pressure and temperature conditions of internal combustion engines and
blast furnaces
Exhaust gases also contain unburned hydrocarbons and carbon monoxide
Cars are fitted with catalytic converters which form a part of their exhaust systems
Their function is to render these exhaust gases harmless
Adverse Effects
Acid rain with similar effects as SO2 as well as producing photochemical smog and
breathing difficulties, in particular for people suffering from asthma
Catalytic Converters
They contain a series of transition metal catalysts including platinum and
rhodium
The metal catalysts are in a honeycomb within the converter to increase the
surface area available for reaction
A series of redox reactions occurs which neutralises the pollutant gases
Carbon monoxide is oxidised to carbon dioxide:
2CO + O2 → 2CO2

Nitrogen oxides are reduced to N2 gas:

2NO → N2 + O2

2NO 2 → N 2 + 2O 2

Unburned hydrocarbons are oxidised to carbon dioxide and water:

C8H18 + 12½O2 → 8CO2 + 9H2O

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

Catalytic converters are designed to reduce the polluting gases produced in car
exhausts

Formation of Sulfur Dioxide

Sulfur dioxide
Sources: combustion of fossil fuels - especially coal
Fossil fuels are often contaminated with small amounts of sulfur impurities
When these contaminated fossil fuels are combusted, the sulfur in the fuels
get oxidised to sulfur dioxide
S (s) + O2 (g) → SO2 (g)

Adverse effects: acid rain which causes corrosion to metal structures, buildings
and statues made of carbonate rocks, damage to aquatic organisms. Pollutes crops
and water supplies, irritates lungs, throats and eyes

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Acid Rain YOUR NOTES



Formation of acid rain from nitrogen and sulfur oxides

The sulfur dioxide produced from the combustion of fossil fuels dissolves in
rainwater droplets to form sulfuric acid
2SO2 (g) + O2 (g) + 2H2O (l) → 2H2SO4 (aq)

Sulfuric acid is one of the components of acid rain which has several damaging
impacts on the environment
Nitrogen dioxide produced from car engines reacts with rain water to form a
mixture of nitrous and nitric acids, which contribute to acid rain:
2NO2 (g) + H2O (l) → HNO2 (aq) + HNO3 (aq)

Lightning strikes can also trigger the formation of nitrogen monoxide and nitrogen
dioxides in air
Nitrogen dioxide gas reacts with rain water and more oxygen to form nitric acid
4NO2 (g) + 2H2O (l) + O2 (g)→ 4HNO3 (aq)

When the clouds rise, the temperature decreases, and the droplets get larger
When the droplets containing these acids are heavy enough, they will fall down as
acid rain

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4.2.4 Cracking YOUR NOTES


Cracking
Saturated molecules contain single bonds only whereas unsaturated molecules
contain double bonds between their carbon atoms
Alkanes are saturated compounds and alkenes are unsaturated compounds
Long chain alkane molecules are further processed to produce other products
consisting of smaller chain molecules
A process called cracking is used to convert them into short chain molecules
which are more useful
Small alkenes and hydrogen are produced using this process
Kerosene and diesel oil are often cracked to produce petrol, other alkenes and
hydrogen
There are two methods used to crack alkanes: catalytic cracking and steam
cracking
As the names suggest, one method uses a catalyst and the other uses steam

Decane is cracked to produce octane for petrol and ethene for ethanol synthesis

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Catalytic cracking involves heating the hydrocarbon molecules to around 470 – YOUR NOTES
550°C to vaporise them 
The vapours then pass over a hot powdered catalyst of aluminium oxide
This process breaks covalent bonds in the molecules as they come into contact
with the surface of the catalyst, causing thermal decomposition reactions
The molecules are broken up in a random way which produces a mixture of
smaller alkanes and alkenes
Hydrogen and a higher proportion of alkenes are formed at higher temperatures
and higher pressure

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Fraction Supply & Demand YOUR NOTES

Crude oils vary considerably in their composition and some need more refining 
than others
Supply is how much of a particular fraction can be produced from refining the
crude oil
Demand is how much customers want to buy
General the demand for certain fractions outstrips the supply so this is why
cracking is necessary to convert surplus unwanted fractions into more useful ones
This is mostly larger, heavier fractions that are cracked into smaller lighter
fractions

Supply & demand graph for crude oil fractions

You can see from the chart that fuel oil and bitumen are surplus fractions so they
are cracked and modified to produce petrol, kerosene and diesel

 Exam Tip
Remember that cracking is an endothermic reaction.

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4.3 Alkanes YOUR NOTES


4.3.1 Alkanes
The Alkanes
Alkanes are a group of saturated hydrocarbons
The term saturated means that they only have single carbon-carbon bonds,
there are no double bonds
The general formula of the alkanes is CnH2n+2
They are colourless compounds which have a gradual change in their physical
properties as the number of carbon atoms in the chain increases
Alkanes are generally unreactive compounds but they do undergo combustion
reactions, can be cracked into smaller molecules and can react with halogens in
the presence of light
Methane is an alkane and is the major component of natural gas

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YOUR NOTES


This table shows the first five members of the alkane homologous series

 Exam Tip
For your exam, you need to be able to name, draw and give the appropriate
formula for the first five alkanes.

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4.3.2 Halogens & Alkanes YOUR NOTES


Halogens & Alkanes
In a substitution reaction, one atom is swapped with another atom
Alkanes undergo a substitution reaction with halogens in the presence of
ultraviolet radiation

In the presence of ultraviolet (UV) radiation, methane reacts with bromine in a

substitution reaction

The equation for the reaction is

CH4 + Br2 → CH3Br + HBr

methane + bromine → bromomethane + hydrogen bromide

Chlorine will also react with alkanes to form chloromethane

CH4 + Cl2 → CH3Cl + HCl

methane + chlorine → chloromethane + hydrogen chloride

The products belong to a family called halogenoalkanes or haloalkanes

Halogenoalkanes have many uses a solvents, refrigerants, propellants and
pharmaceuticals

 Exam Tip
CFC stands for chlorofluorocarbon, an important class of halogenoalkanes,
previously used in fridges and air conditioners, but gradually being phased
out because of the damage they cause to the ozone layer.

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4.4 Alkenes YOUR NOTES


4.4.1 Alkenes
The Alkenes
All alkenes contain a double carbon bond, which is shown as two lines between
two of the carbon atoms i.e. C=C
All alkenes contain a double carbon bond, which is the functional group and is
what allows alkenes to react in ways that alkanes cannot
The names and structure of the first four alkenes are shown below:
Table Showing the Formulae and Structures of the First Four Alkenes

Compounds that have a C=C double bond are also called unsaturated compounds
That means they can make more bonds with other atoms by opening up the C=C
bond and allowing incoming atoms to form another single bond with each carbon
atom of the functional group

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Each of these carbon atoms now forms 4 single bonds instead of 1 double and 2 YOUR NOTES
single bonds 
This makes them much more reactive than alkanes

A carbon-carbon double can break and form a single bond, allowing more atoms to
attach to the carbon atoms

 Exam Tip
The numbers in butene, pentene and hexene refer to the carbon atom in
which the C=C begins, counting from the left. E.g. pent-2-ene, C5H10 has
the C=C between the 2nd and 3rd carbon atoms. In pent-3-ene the C=C bond
is between the 3rd and 4th carbon atoms from the left.

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4.4.2 Bromine & Alkenes YOUR NOTES


Bromine & Alkenes
Alkenes are a homologous series of hydrocarbon compounds with at least
one double bond between two of the carbon atoms on the chain
The double bond can be written as carbon carbon double bond or as C=C
The general formula for alkenes is:
C nH2n

Alkenes are generally more desirable than alkanes as they are more reactive due
to the presence of the carbon-carbon double bond, so they can take part in
reactions in which alkanes cannot, making them more useful than alkanes
They are used to make polymers and are the starting materials for the production
of many other chemicals
Two useful reactions are the bromination of alkenes and polymerisation
Bromination of Ethene
Alkenes undergo addition reactions in which atoms of a simple
molecule add across the C=C double bond
The reaction between bromine and ethene is an example of an addition reaction
The same process works for any halogen and any alkene in which the halogen
atoms always add to the carbon atoms across the C=C double bond

Bromine atoms add across the C=C in the addition reaction of ethene and bromine

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Testing for Alkenes YOUR NOTES

Bromine Water Test 
Alkanes and alkenes have different molecular structures
All alkanes are saturated and alkenes are unsaturated
The presence of the C=C double bond allows alkenes to react in ways that alkanes
cannot
This allows us to tell alkenes apart from alkanes using a simple chemical test
called the bromine water test

Diagram showing the result of the test using bromine water with alkanes and alkenes

Bromine water is an orange coloured solution

When bromine water is added to an alkane, it will remain as an orange solution as
alkanes do not have double carbon bonds (C=C) so the bromine remains in
solution
But when bromine water is added to an alkene, the bromine atoms add across the
C=C bond, hence the solution no longer contains free bromine so it loses its
colour

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YOUR NOTES
 Exam Tip
Alkenes are more reactive than alkanes due to the presence of the carbon- 
carbon double bond which contains an area of high electron density.

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4.5 Alcohols YOUR NOTES


4.5.1 Alcohols
The Alcohols
Alcohols are colourless liquids that dissolve in water to form neutral solutions
The first four alcohols are commonly used as fuels
Methanol and ethanol are also used extensively as solvents
This is because they can dissolve many substances that water cannot such
as fats and oils, but can also dissolve most of the substances that water can
The names and structures of the first four alcohols are shown below
In terms of naming, the same system is used as for alkanes and alkenes, with the
final ‘e’ being replaced with ‘ol’
Table Showing the Formulae and Structures of the First Four Alcohols

 Exam Tip
It is standard practice to write the functional group on the end as it shows
what the molecule is. E.g. Methanol is CH3OH, not CH4O.

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4.5.2 Oxidation of Ethanol YOUR NOTES


Oxidation of Ethanol
Ethanol can undergo oxidation in three different ways:
Combustion
Aerobic oxidation
Treatment with an oxidising agent
Combustion
Alcohols undergo combustion to form carbon dioxide and water
The complete combustion of ethanol is as follows:

Ethanol burns readily with an almost invisible blue flame

School laboratories use ethanol in spirit burners as it burns cleanly and without
strong odours
Aerobic Oxidation
Bacteria in the air (acetobacter) use atmospheric oxygen from air to oxidise the
ethanol in the wine:
ethanol + oxygen → ethanoic acid + water

The acidic, vinegary taste of wine which has been left open for several days is due
to the presence of ethanoic acid
This is what happens to wine when it is left open as the microbial oxidation of
ethanol will produce a weak solution of the carboxylic acid, ethanoic acid, the
same acid used in vinegar
Treatment with an oxidising agent
Alcohols undergo oxidation to produce carboxylic acids when treated with
oxidising agents
When ethanol is heated with acidified potassium dichromate solution the ethanol
oxidises to ethanoic acid
The equation for the reaction is:
CH3CH2OH + [O] → CH3COOH + H2O

The oxidising agent is represented by the symbol for oxygen in square brackets
The reaction is slow so the mixture is heated to its boiling point for about an hour;
to avoid the substances evaporating a condenser is placed above the reaction flask
that prevents volatile liquids from escaping
During the reaction the potassium dichromate turns from orange to green

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YOUR NOTES


Ethanol can be oxidised by heating it with potassium dichromate in sulfuric acid. The
solution turns from orange to green during the reaction

 Exam Tip
Be careful when writing the equation for the combustion of ethanol-
students often forget to include the oxygen in the ethanol when balancing
the equation.

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4.5.3 Manufacture of Ethanol YOUR NOTES


Industrial Synthesis of Ethanol
Ethanol can be synthesised by the hydration of ethene
Ethene is a by-product of the cracking of hydrocarbons and is a valuable feedstock
for making many chemicals
The hydration reaction is very important industrially for the production of alcohols
and it occurs using the following conditions:
Temperature of around 330ºC
Pressure of 60 – 70 atm
Concentrated phosphoric acid catalyst
When the reaction is complete, the reaction chamber holds unreacted ethene,
ethanol and water
The contents are transferred to a condenser where ethene is separated easily as it
has a much lower boiling point than ethanol and water:
Ethanol: 78oC
Ethene: -103oC
Water: 100oC
The ethanol and water are separated afterwards by fractional distillation

A water molecule adds across the C=C in the hydration of ethene to produce ethanol

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Fermentation YOUR NOTES

Ethanol (C2H5OH) is one of the most important alcohols 
It is used as fuel (for vehicles in some countries) and as a solvent
It is the type of alcohol found in alcoholic drinks such as wine and beer
It can be produced by fermentation where sugar or starch is dissolved in water and
yeast is added
The mixture is then fermented between 15 and 35°C with the absence of oxygen
for a few days
Yeast contains enzymes that break down sugar to alcohol
If the temperature is too low the reaction rate will be too slow and if it is too high
the enzymes will become denatured
The yeast respires anaerobically using the glucose to form ethanol and carbon
dioxide:
C6H12O6 + enzymes → 2CO2 + 2C2H5OH

The yeast is killed off once the concentration of alcohol reaches around 15%, hence
the reaction vessel is emptied and the process is started again
This is the reason that ethanol production by fermentation is a batch process

 Exam Tip
Fermentation is an anaerobic process. Oxygen is not required for ethanol to
be produced by fermentation.

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4.6 Carboxylic acids YOUR NOTES


4.6.1 Carboxylic Acids
The Carboxylic Acids
Carboxylic acids is the name given to compounds containing the functional
group carboxyl, -COOH
The general formula of a carboxylic acid is CnH2n+1COOH which can be shortened
to just RCOOH
The naming of a carboxylic acid follows the pattern alkan + oic acid
The names and structure of the first four carboxylic acids are shown below

The structures and formulae of the first four carboxylic acids

 Exam Tip
Vinegar is an aqueous solution of ethanoic acid and contains about 5% of
the acid by volume.

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4.6.2 Reactions of Carboxylic Acids YOUR NOTES


Reactions of Carboxylic Acids
The carboxylic acids behave like other acids
They react with metals to form a salt and hydrogen and with carbonates to form a
salt, water and carbon dioxide gas
They take part in neutralisation reactions to produce salt and water
Ethanoic acid (also called acetic acid ) is the acid used to make vinegar, which
contains around 5% by volume ethanoic acid
The salts formed by the reaction of carboxylic acids all end –anoate
So methanoic acid forms a salt called methanoate, ethanoic a salt called ethanoate
etc
In the reaction with metals, a metal salt and hydrogen gas are produced
For example in the reaction of ethanoic acid with magnesium, the salt
magnesium ethanoate is formed:
2CH3COOH + Mg → (CH3COO)2Mg + H2

In the reaction with hydroxides a salt and water are formed in

a neutralisation reaction
For example in reaction with potassium hydroxide the salt potassium propanoate
is formed by reaction with propanoic acid:
CH3CH2COOH + KOH → CH3CH2COOK + H2O

In the reaction with carbonates a metal salt, water and carbon dioxide gas are
produced
For example in reaction with potassium carbonate the salt potassium butanoate is
formed by reaction with butanoic acid:
2CH3CH2CH2COOH + K2CO3 → 2CH3CH2CH2COOK + H2O + CO2

 Exam Tip
You are not expected to be able to write balanced equations for the
reactions of carboxylic acids- they are included here for background
information.

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4.7 Esters YOUR NOTES


4.7.1 Esters
The Esters
Making Esters
Alcohols and carboxylic acids react to make esters in esterification reactions
Esters are compounds with the functional group R-COO-R
Esters are sweet-smelling oily liquids used in food flavourings and perfumes
Ethanoic acid will react with ethanol in the presence of concentrated sulfuric acid
(catalyst) to form ethyl ethanoate:
CH3COOH + C 2H5OH → CH3COOC 2H5 + H2O

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YOUR NOTES


Diagram showing the formation of ethyl ethanoate

Naming Esters
An ester is made from an alcohol and carboxylic acid
The first part of the name indicates the length of the carbon chain in the alcohol,
and it ends with the letters ‘- yl’
The second part of the name indicates the length of the carbon chain in the
carboxylic acid, and it ends with the letters ‘- oate’
e.g. the ester formed from pentanol and butanoic acid is called pentyl butanoate

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YOUR NOTES


Diagram showing the origin of each carbon chain in ester

Some examples of common esters:

Examples of Esters Table

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4.7.2 Practical: Preparation of Ethyl Ethanoate YOUR NOTES


Practical: Preparation of Ethyl Ethanoate
Aim:

To prepare a small sample of ethyl ethanoate

Diagram:

The preparation of ethyl ethanoate

Method:

A mixture of ethanoic acid, ethanol and concentrated sulfuric acid is gently heated
by either a water bath or an electric heater (ethanol is flammable, so a Bunsen
can’t be used!)
The ester is then distilled off as soon as it is formed and collected in a separate
beaker by condensation
As esters have low boiling points (they are volatile), they are the first to evaporate
from the reaction mixture. Removing them from the mixture by distillation
prevents the reverse reaction from occurring
Result:
The distillate can be smelt to check whether an ester has been produced
Small quantities of ethanoic acid, sulfuric acid and ethanol can also be collected in
the process
To remove acidic impurities, sodium carbonate solution can be added, until the
mixture stops fizzing (no more carbon dioxide is evolved)
To remove ethanol, calcium chloride solution can be added

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4.8 Synthetic polymers YOUR NOTES


4.8.1 Addition Polymers
Monomers
Polymers are large molecules of high relative molecular mass and are made by
linking together large numbers of smaller molecules called monomers
Each monomer is a repeat unit and is connected to the adjacent units via covalent
bonds
Polymerisation reactions usually require high pressures and the use of a catalyst
Many everyday materials such as resins, plastics, polystyrene cups, nylon etc. are
polymers
These are manufactured and are called synthetic polymers
Nature also produces polymers which are called natural or biological polymers

Diagram showing how lots of monomers bond together to form a polymer

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Drawing Polymers YOUR NOTES

Addition polymers are formed by the joining up of many monomers and only 
occurs in monomers that contain C=C bonds
One of the bonds in each C=C bond breaks and forms a bond with the adjacent
monomer with the polymer being formed containing single bonds only
Many polymers can be made by the addition of alkene monomers
Others are made from alkene monomers with different atoms attached to
the monomer such as chlorine or a hydroxyl group
The name of the polymer is deduced by putting the name of the monomer in
brackets and adding poly- as the prefix
For example if propene is the alkene monomer used, then the name
is polypropene
Polyethene is formed by the addition polymerisation of ethene monomers

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YOUR NOTES


Examples of addition polymerisation: polyethene and PVC

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Deducing Monomers & Repeat Units YOUR NOTES

Deducing the monomer from the polymer 
Polymer molecules are very large compared with most other molecule
Repeat units are used when displaying the formula
To draw a repeat unit, change the double bond in the monomer to a single bond in
the repeat unit
Add a bond to each end of the repeat unit
The bonds on either side of the polymer must extend outside the brackets (these
are called extension or continuation bonds)
A small subscript n is written on the bottom right hand side to indicate a large
number of repeat units
Add on the rest of the groups in the same order that they surrounded the double
bond in the monomer

Diagram showing the concept of drawing a repeat unit of a monomer

Deducing the polymer from the monomer

Identify the repeating unit in the polymer
Change the single bond in the repeat unit to a double bond in the monomer
Remove the bond from each end of the repeat unit and the subscript n (which can
be placed in front of the monomer)

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YOUR NOTES


Diagram showing the monomer of the repeat unit of polymer

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4.8.2 Disposal of Addition Polymers YOUR NOTES


Disposal of Addition Polymers
Addition polymers are formed by the joining up of many small molecules with
strong C-C bonds
This makes addition polymers unreactive and chemically inert so don’t easily
biodegrade

Disposal of addition polymers is an environmental problem

Landfills
Waste polymers are disposed off in landfill sites but this takes up valuable land, as
addition polymers are non-biodegradable so micro-organisms such as
decomposers cannot break them down
This causes sites to quickly fill up
Incineration
Polymers release a lot of heat energy when they burn and produces carbon dioxide
which is a greenhouse gas that contributes to climate change
Polymers that contain chlorine such as PVC release toxic hydrogen chloride gas
when burned
If incinerated by incomplete combustion, carbon monoxide will be produced which
is a toxic gas that reduces the capacity of the blood to carry oxygen
Recycling
Polymers can be recycled but different polymers must be separated from each
other
This process is difficult and expensive

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4.8.3 Condensation Polymers YOUR NOTES


Condensation Polymers
Condensation polymers are formed when two different monomers are linked
together with the removal of a small molecule, usually water
This is a key difference between condensation polymers and addition polymers:
Addition polymerisation forms the polymer molecule only
Condensation polymerisation forms the polymer molecule and
one water molecule per linkage
The monomers have two functional groups present, one on each end
The functional groups at the ends of one monomer react with the functional group
on the end of the other monomer, in so doing creating long chains of alternating
monomers, forming the polymer
Polyesters are formed from two different monomers and produce water
For every ester linkage formed in condensation polymerisation, one molecule of
water is formed from the combination of a -H and an -OH group
An example is terylene which is a polyester made from dicarboxylic acid
monomers (a carboxylic with a -COOH group at either end) and diols (an alcohol
with an -OH group at either end)
Each -COOH group reacts with another -OH group on another monomer
An ester linkage is formed with the subsequent loss of one water molecule per link

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YOUR NOTES


The condensation reaction in which the polyester terylene is produced

The structure of terylene can be represented by drawing out the polymer using
boxes to represent the carbon chains
This can be done for all polyesters

Diagram showing a section of the polyester terylene

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YOUR NOTES
 Exam Tip
Notice that the sequence of bonding in the polyester is the mirror image at 
either end of the link, NOT the link repetition due to the monomers
containing the same functional group at either end.

Biopolyesters
Biopolyesters are a specific type of polymers that are synthesised from sugars and
plant oils using microorganisms
They are able to biodegrade naturally in the environment after their intended
purpose
The polymers are synthetically made, consisting of ester, amide and ether
functional groups which gives them the characteristic of being biodegradable

The biodegradation of a bottle made of biopolyesters

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