A2 Chemistry: F324- Rings, Polymers, and Analysis.

Addition Polymers and Poly(esters).

Learning Outcomes:
All (E)
• State the two types of polymerisation reactions.
• State and draw the monomers used to make Terylene and poly(lactic acid)
Most (C)
• Draw the repeating unit given the structure of a polymer
• Identify the monomers given a section of a polymer
Some (A)
• Write an equation to show the polymerisation of Terylene and poly(lactic acid)

Polymerisation – a reaction in which small molecules called monomers join together to make large molecules
consisting of repeating units.

There are two general types of polymerisation, addition and condensation.

Addition Polymerisation.

Involves an alkene where the π(pi) bond is broken enabling connecting covalent bonds to be formed. Addition
polymerisation involves no loss of atoms/molecules.

The formation of poly(ethene) from its monomer ethene.

The repeating unit of poly(ethene) is:

Draw a polymerisation reaction of poly(propene) showing one repeating unit.

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 Draw the repeating unit in the following polymers;

a. Poly(chloroethene)

b. Poly(tetrafluoroethene)

c. Poly(phenylethene)/poly(styrene)

Condensation Polymerisation.
A reaction in which two small molecules react together to form a larger molecules, with the elimination of a small
molecules such as water or HCl.

• Condensation polymerisation requires two monomers that have different functional groups, where the
different functional groups bond together or one monomer that contains two different functional groups..
Condensation polymerisation monomers are bifunctional (contain two functional groups e.g. amino acid)
or are different.
• Polyester and polyamides are common condensation polymers.

Polyesters

Polyesters are made from monomers that contain a dicarboxylic group and an diol group. The reaction is the
same as forming esters which you have covered earlier in the unit. The two common types of polyesters are:

1. Polyesters made by reacting two different types of monomers units

One monomer is a dicarboxylic acid (two -COOH groups)

One monomer is a diol (two –OH groups)

2. Polyesters made by reacting just one type of monomer unit containing both –OH groups and -COOH

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 Draw the general equations for the formation of the two different types of poly(ester)

Formation of polyester from two monomers one Formation of polyester from one monomer
containing a diol and the other containing a dicarboxylic (hydroxycarboxylic acid)
acid

Condensation Polymerisation Reaction to Form Terylene (a polyester).

This is an example of forming a polymer from two different monomers. The reaction is a condensation
polymerisation reaction where the hydroxyl group of one monomer forms an ester link with the carboxylic acid
group of the other monomer. Water is eliminated during the reaction.

The monomers are:

1. Benzene-1,4-dicarboxylic acid
2. Ethane-1,2-diol

The formation of polyester (Terylene) is made from two monomers as shown above. When these two
monomers react the alcohol group will lose a hydrogen and the carboxylic acid group will lose an hydroxyl group
to form an ester link and water is eliminated.

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Poly(esters) are strong fibres which are inelastic and are resistant to shrinking and chemical attack, but they are
easily combustible.

Uses of Terylene:

1……………………………………………………………………………………………………………………….

2. ……………………………………………………………………………………………………………………….

3. ……………………………………………………………………………………………………………………….

4. ……………………………………………………………………………………………………………………….

Properties of Terylene:

1. ……………………………………………………………………………………………………………………….

2. ……………………………………………………………………………………………………………………….

3. ……………………………………………………………………………………………………………………….

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Condensation Polymerisation Reaction to Form Poly(lactic acid) –a polyester.
This is an example of forming a polymer from one monomer 2-hydroxypropanic acid
(lactic acid). Poly(lactic acid) is the polymer that makes clear plastic cups and is made from the
polymer lactic acid (2-hydroxypropanic acid).

Poly(lactic acid) is biodegradable so is becoming widely used in drinks and food containers.
During the condensation reaction an ester bond (-COO-) forms between the
hydroxyl group on one monomer and the dicarboxylic group on the other monomer.
Water is eliminated during the reaction

Monomer
2-hydroxypropanoic Acid

Questions.

1. Short sections of the molecular structures of two polymers are shown below.
H H H H H H

C C C C C C

H H H

polymer C

O O H H O O H H

C C O C C O C C O C C O

H H H H
polymer D

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 (a) (i) Circle, on the diagrams above, the simplest repeat unit in each polymer.
[2]

(ii) In the boxes below, draw the displayed formulae of the two monomers that could
be used to prepare polymer D.

[2]

(b) Chemists have developed degradable polymers to reduce the quantity of plastic waste
being disposed of in landfill sites. Polymer D is more likely to be a ‘degradable polymer’
than polymer C.

Suggest two reasons why.

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[2]
[Total 6 marks]
2. Poly(phenylethene) is one of the most versatile and successful polymers.

The 3-D skeletal formula of a section of atactic poly(phenylethene) is shown in the diagram
below.

(i) State the type of polymerisation used to make poly(phenylethene).

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[1]

C:\Users\Paul McCormack\Desktop\Addition Polymers and Polyester Student Notes.docx/P.J.McCormack/12-10-12

 (ii) Draw a skeletal or displayed formula to show the monomer used to make
poly(phenylethene).

[1]

(iii) Outline how the polymer is formed from the monomer molecules. (You do not need to
give any details of the catalyst or conditions involved.)

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[2]
[Total 4 marks]

Tell me two things….

…that you have done well today
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…that you know now that you didn’t know at the start of the lesson
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…that you could have done better next lesson

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…that you would like to know more about

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Notes.

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Further Information.

1. Chemguide – Addition Polymeriation Reactions.

http://bit.ly/fRCL0g

2. Chemguide – Terylene

http://bit.ly/yFDYOu

3. You Tube Addition Polymerisation video

http://bit.ly/RoyjdL

4. Knock Hardy Notes.

http://bit.ly/rho0KY Download the Layer app for iPhone or

Android to access the interactive
5. AS Textbook pages 54-55 & 58-59. material where every you see the icon.

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