A Level Chemistry CIE

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YOUR NOTES
A Level Chemistry CIE 
7.7 Polymerisation (A Level Only)
CONTENTS
7.7.1 Formation of Polyesters
7.7.2 Formation of Polyamides
7.7.3 Repeat Units & Monomers
7.7.4 Predicting & Deducing the Type of Polymerisation
7.7.5 Degradabiity of Polymers
Page 1 of 20
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7.7.1 Formation of Polyesters YOUR NOTES


Formation of Polyesters
Addition polymerisation has been covered in reactions of alkenes
They are made using monomers that have C-C double bonds joined together to form
polymers such as (poly)ethene
Condensation polymerisation is another type of reaction and is used in the making of
polyesters
A small molecule (eg. a water molecule) is lost when the monomers join together to
form a polyester
Polyesters contain ester linkages
This polymer structure shows an ester functional group linking monomers together
Formation of polyesters
A diol and a dicarboxylic acid are required to form a polyester
A diol contains 2 -OH groups
A dicarboxylic acid contains 2 COOH groups
The position of the functional groups on both of these molecules allows condensation
polymerisation to take place effectively
When the polyester is formed, one of the -OH groups on the diol and the hydrogen atom of
the -COOH are expelled as a water molecule (H2O)
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The resulting polymer is a polyester YOUR NOTES


Expulsion of a water molecule in this condensation polymerisation forms the polyester

called Terylene (PET)
Hydroxycarboxylic acids
So far the examples of making polyesters have focused on using 2 separate monomers for
the polymerisation
There is another route to making polyesters
A single monomer containing both of the key functional groups can also be used
These monomers are called hydroxycarboxylic acids
They contain an alcohol group (-OH) at one end of the molecule while the other end is
capped by a carboxylic acid group (-COOH)
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YOUR NOTES

Both functional groups are needed to make a polyester are from the same monomer
 Exam Tip
Polyesters can be made using condensation polymerisation
The monomers needed are diols and dicarboxylic acids/dioyl chlorides or a
single hydroxycarboxylic acid monomer
Page 4 of 20
7.7.2 Formation of Polyamides YOUR NOTES


Formation of Polyamides
Amide link
Polyamides are also formed using condensation polymerisation
An amide link - also known as a peptide link - is the key functional group in a polyamide
Monomers
A diamine and a dicarboxylic acid are required to form a polyamide
A diamine contains 2 -NH2 groups
A dicarboxylic acid contains 2 -COOH groups
Dioyl dichlorides can also used to react with the diamine instead of the acid
A dioyl chloride contains 2 -COCl groups
This is a more reactive monomer than dicarboxylic acid. However, a more expensive
alternative
Page 5 of 20
YOUR NOTES

The monomers for making polyamides

Formation of polyamides
This shows the expulsion of a small molecule as the amide link forms
Nylon 6,6 is a synthetic polyamide
Its monomers are 1,6-diaminohexane and hexane-1,6-dioic acid
Page 6 of 20
The ‘6,6’ part of its name arises from the 6 carbon atoms in each of Nylon 6,6 YOUR NOTES
monomers 
Nylon 6,6 is a synthetic polyamide made using diamine and dicarboxylic acid monomers
Kevlar
Kevlar is another example of a polymer formed through condensation polymerisation
The polymer chains are neatly arranged with many hydrogen bonds between them
This results in a strong and flexible polymer material with fire resistance properties
These properties also lend Kevlar to a vital application in bullet-proof vests
The monomers used to make Kevlar
1,4-diaminobenzene
Benzene-1,4-dicarboxylic acid
As seen with Nylon, a dioyl chloride can be used instead of the acid as well (benzene-1,4-
dioyl chloride)
Page 7 of 20
YOUR NOTES

Kevlar is made using a diamine and dicarboxylic acid monomers

Aminocarboxylic acids
So far, condensation polymerisation has covered the use of monomers that contain 2 of
the same functional group (eg. diamine, Diol etc.)
It is possible to carry out a condensation polymerisation where one monomer provides
both of the function groups necessary for an amide/peptide link
For example 6-aminohexanoic acid has an amino group and a carboxylic acid group on the
same molecule
Molecules like this are called amino carboxylic acids
They are able to polymerise to form a structure similar to Nylon 6,6
Page 8 of 20
YOUR NOTES

6-aminohexanoic acid can be polymerised to make the synthetic polymer Nylon 6,6
Making Proteins
Proteins are vital biological molecules with varying functions within the body
They are essentially polymers made up of amino acid monomers
Amino acids have an aminocarboxylic acid structure
Their properties are governed by a branching side group - the R group
Amino acids contain an amine group, an acid group and a unique R group
Page 9 of 20
Different amino acids are identified by their unique R group YOUR NOTES
The names of each amino acid is given using 3 letters 
For example Glutamine is known as ‘Gln’
Dipeptides can be produced by polymerising 2 amino acids together
The amine group (-NH2) and acid group (-COOH) of each amino acid is used to
polymerise with another amino acid
Polypeptides are made through polymerising more than 2 amino acids together
Dipeptides and polypeptides are formed by polymerising amino acid molecules together
Protein hydrolysis
Proteins (polypeptides) can be broken down into its constituent amino acids
This process occurs through a hydrolysis reaction
Page 10 of 20
YOUR NOTES

Proteins are broken down by hydrolysis
 Exam Tip
Become familiar with the structures of the different monomers that can be used to
make condensation polymers.Also, remember that exam questions will require you
to identify the key functional groups and also draw small sections of polymers.
Page 11 of 20
7.7.3 Repeat Units & Monomers YOUR NOTES


Deducing the Repeat Unit of a Condensation Polymer
In condensation polymerisation the monomers either contain 2 of the same functional
group or one single monomer has both functional groups needed for polymerisation
For example Diamine and dicarboxylic acid
Or an aminocarboxylic acid
When presented with 2 monomers there are steps to take in order to deduce the repeat unit
of a condensation polymer
 Exam Tip
Remember: in condensation polymerisation, a small molecule is expelled as a
result of the 2 monomers joining together.
When a dioic acid and diamine polymerise, a water molecule is expelled
OH from acid and H from the amine
When a dioyl acid and diamine are polymerised, a hydrochloric acid molecule is
expelled
Cl from the dioyl acid and H from the amine
Identifying Monomers in Condensation Polymers

When a section of polymer is presented, the monomers can be identified by considering
the small molecules expelled from the monomers
If a water molecule is expelled, the -OH must have been from an acid group
The hydrogen atom may be from an amine group of a monomer.
If the molecule was hydrochloric acid (HCl), a dioyl chloride monomer may have been used
Page 12 of 20
7.7.4 Predicting & Deducing the Type of Polymerisation YOUR NOTES


Predicting Type of Polymerisation
When a set of monomers are given in an exam question, the type of polymerisation can be
determined
Firstly, it’s important to identify the key functional groups in the monomers
Addition polymerisation
If the monomer/s contain a C=C double bond, they will polymerise through addition
polymerisation
The double bond can open up in order to add more monomers either side of the starting
monomer
This type of polymerisation makes (poly)alkenes
Addition polymerisation of one alkene monomer is polymerised, a (poly)alkene is formed

(Poly)alkenes can be produced if there are 2 or more alkene monomers as well
When more than one monomer is used for addition polymerisation, the resulting product is
known as a copolymer
Page 13 of 20
YOUR NOTES

Two or more different alkene monomers can also be polymerised in Addition polymerisation.
This gives a co-polymer
Condensation polymerisation
Condensation polymerisation makes polyamides and polyesters
When looking to identify this type of polymerisation, there are some key functional groups
to be aware of
Page 14 of 20
Monomers for condensation polymers table YOUR NOTES


 Exam Tip
As well as the functional groups to be aware of, know that a small molecule is
expelled when the polymer is formed
Identify 2 functional groups that can react together to produce either a
polyamide or a polyester
There are instances where both of the functional groups are on the same
monomer molecule
For example amino acid molecules contain an amine group (-NH2) and a
carboxylic acid group (-COOH) therefore it can polymerise to produce a
polyamide
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Deducing Type of Polymerisation YOUR NOTES

The type of polymerisation can be determined by considering the structure of the polymer 
backbone
Identifying addition polymerisation
The polymer backbone of an addition polymer does not contain functional groups
The backbone of the polymer is generally a chain of carbon atoms
There may be sidechains branching off from the backbone
Some examples of side chains are benzene rings, nitrile groups (-CN) and halogen atoms (-
F/-Cl/-Br/-I)
Addition polymers are identified using the plain carbon chain as the polymer backbone
Identifying condensation polymerisation
A condensation polymer can be identified by functional groups on the polymer backbone
Polyesters contain ester links and polyamides contain amide/peptide link on the backbone
itself
Condensation polymers are identified using function groups that form parts of the polymer
backbone
Page 16 of 20
Exam Tip YOUR NOTES

 
Different sections of polymer chains may be formed using various type of
polymerisation
In an exam, you may be given a section of a polymer and asked to determine the
type of polymerisation used to form that section
Firstly, look at the polymer backbone
If there are functional groups along the backbone, that section was made
using condensation polymerisation
If there are no functional groups along the backbone, addition
polymerisation was used
Page 17 of 20
7.7.5 Degradabiity of Polymers YOUR NOTES


Poly(alkenes) & Biodegradability
Many of the polymers in use have been produced through addition polymerisation of
alkenes
The (poly)alkene chains are non-polar and saturated
This makes them chemically inert and, therefore, non-biodegradable
(Poly)alkenes can be melted and recycled for new uses
However, even in the new applications, the (poly)alkenes are not biodegradable
Recycling plants can burn used plastic materials
The energy released from burning can be used to generate electricity
Burning plastics in oxygen releases carbon dioxide and water (complete combustion)
which can contribute to global warming
Photodegradation of Polymers
Polyesters and polyamides are biodegradable polymers for a number of reasons
One such reason is their ability to breakdown with the use of light
Carbonyl groups (C=O) along polymer chains are able to absorb energy from the
Electromagnetic Spectrum, in particular ultraviolet (UV) light
Absorbing UV light weakens the carbonyl areas of polymers and breaks them down
into smaller molecules
Disadvantages of photo degradability
Despite this ability being a great advantage of polyesters and polyamides, it may pose
problems when the polymers are repurposed
When applied to a new use, the biodegradability could give a weaker polymer
Breaking down polymers also poses another challenge
Once used, polymeric materials are taken to landfill sites where many other materials
are piled on top of each other
This could mean that photodegradable polyesters or polyamides do not have access
to UV light in order to break down naturally
Page 18 of 20
Biodegrading Polyesters & Polyamides YOUR NOTES

Biodegradable polymers 
Both polyesters and polyamides can be broken down using hydrolysis reactions
This is a major advantage over the polymers produced using alkene monomers
(polyalkenes)
When polyesters and polyamides are taken to landfill sites, they can be broken down easily
and their products used for other applications
Hydrolysis of polyamides
Hydrolysis is the breakdown of molecules using water
In acidic hydrolysis, an acid (such as hydrochloric acid) acts as the catalyst
Polyamides such as Kevlar are heated with dilute acid
This reaction breaks the polyamide into a dicarboxylic acid and ammonium ions
Alkaline hydrolysis
The polyamide is heated with a species containing hydroxide ions (eg. sodium
hydroxide)
This breaks the polymer into the sodium salts of its monomers (dicarboxylic acid salt
and diamines)
Hydrolysis of Kevlar, a polyamide

Hydrolysis of polyesters
Ester linkages can also be degraded through hydrolysis reactions
The acidic and alkaline hydrolysis of polyethylene terephthalate (PET) is shown below
Acid hydrolysis forms the diol and dicarboxylic acid that were used to form the polyesters
Alkaline hydrolysis forms the diol and dicarboxylic acid salt
Page 19 of 20
YOUR NOTES

Hydrolysis of polyethylene terephthalate (PET), a polyester
Page 20 of 20

A Level Chemistry CIE

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A Level Chemistry CIE

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7.7 Polymerisation (A Level Only)

7.7.1 Formation of Polyesters YOUR NOTES

The resulting polymer is a polyester YOUR NOTES

Expulsion of a water molecule in this condensation polymerisation forms the polyester

7.7.2 Formation of Polyamides YOUR NOTES

The monomers for making polyamides

Kevlar is made using a diamine and dicarboxylic acid monomers

Proteins are broken down by hydrolysis

7.7.3 Repeat Units & Monomers YOUR NOTES

Identifying Monomers in Condensation Polymers

7.7.4 Predicting & Deducing the Type of Polymerisation YOUR NOTES

Addition polymerisation of one alkene monomer is polymerised, a (poly)alkene is formed

Monomers for condensation polymers table YOUR NOTES

Deducing Type of Polymerisation YOUR NOTES

Exam Tip YOUR NOTES

7.7.5 Degradabiity of Polymers YOUR NOTES

Biodegrading Polyesters & Polyamides YOUR NOTES

Hydrolysis of Kevlar, a polyamide

Hydrolysis of polyethylene terephthalate (PET), a polyester

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