TH E

CHE MI STR Y
OF POL YME RS
A guide for A level students

KNOCKHARDY PUBLISHING
 KNOCKHARDY PUBLISHING

POLYMERS
INTRODUCTION
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 POLYMERS
CONTENTS
• Prior knowledge
• Types of polymerisation
• Addition polymerisation
• Polymerisation of propene
• Condensation polymerisation
• Peptides
• Check list
 POLYMERS
Before you start it would be helpful to…

• know the functional groups found in organic chemistry

• know the arrangement of bonds around carbon atoms
• recall and explain electrophilic addition reactions of alkenes
 POLYMERISATION

General A process in which small molecules called monomers join

together into large molecules consisting of repeating units.

There are two basic types

ADDITION all the atoms in the monomer are used to form the polymer

CONDENSATION monomers join up the with expulsion of small molecules

not all the original atoms are present in the polymer
 ADDITION POLYMERISATION

• all the atoms in the monomer are used to form the polymer

• occurs with alkenes

• mechanism can be free radical or ionic

 POLYMERISATION OF ALKENES
ADDITION POLYMERISATION

Preparation

Many are prepared by a free radical process involving high pressure, high temperature
and a catalyst. The catalyst is usually a substance (e.g. an organic peroxide) which
readily breaks up to form radicals whichinitiate a chain reaction.

Another famous type of catalyst is a Ziegler-Natta catalyst (named after the scientists
who developed it). Such catalysts are based on the compound TiCl4.

Properties

Physical varied by changing the reaction conditions (pressure, temperature etc).

Chemical have chemical properties based on the functional groups in their structure.
poly(ethene) is typical; it is fairly inert as it is basically a very large alkane.

This means it is resistant to chemical attack and non-biodegradable.

 POLYMERISATION OF ALKENES
ADDITION POLYMERISATION

Process • during polymerisation, an alkene undergoes an addition reaction with itself

• all the atoms in the original alkenes are used to form the polymer
• long hydrocarbon chains are formed

the equation shows the original monomer and the repeating unit in the polymer

n represents a ethene poly(ethene)

large number
MONOMER POLYMER
 POLYMERISATION OF ALKENES
ADDITION POLYMERISATION

the equation shows the original monomer and the repeating unit in the polymer

n represents a ethene poly(ethene)

large number
MONOMER POLYMER
 POLYMERISATION OF ALKENES
EXAMPLES OF ADDITION POLYMERISATION

ETHENE POLY(ETHENE)

PROPENE POLY(PROPENE)

CHLOROETHENE POLY(CHLOROETHENE)
POLYVINYLCHLORIDE PVC

TETRAFLUOROETHENE POLY(TETRAFLUOROETHENE)
PTFE “Teflon”
POLYMERISATION OF ALKENES
SPOTTING THE MONOMER
POLYMERISATION OF ALKENES
SPOTTING THE MONOMER
 POLYMERISATION OF PROPENE - ANIMATION
AN EXAMPLE OF ADDITION POLYMERISATION

PROPENE MOLECULES DO NOT ALWAYS ADD IN A REGULAR WAY

THERE ARE THREE BASIC MODES OF ADDITION

ISOTACTIC
SYNDIOTACTIC
ATACTIC

Animation may not work in

earlier versions of Powerpoint
POLY(PROPENE)

ISOTACTIC
CH3 groups on same side
- most desirable properties
- highest melting point

SYNDIOTACTIC
CH3 groups alternate sided

ATACTIC
random
most likely outcome
 CONDENSATION POLYMERS

• monomers join up the with expulsion of small molecules

• not all the original atoms are present in the polymer

Examples polyamides (nylon)

polyesters (terylene)
peptides
starch

Synthesis reactions between diprotic carboxylic acids and diols

diprotic carboxylic acids and diamines
amino acids

ESTER LINK AMIDE LINK

 POLYESTERS - TERYLENE

Reagents terephthalic acid HOOC-C6H4-COOH

ethane-1,2-diol HOCH2CH2OH

Equation n HOCH2CH2OH + n HOOC-C6H4-COOH ——> -[OCH2CH2OOC(C6H4)CO] n - + n H2O

Product poly(ethylene terephthalate) ‘Terylene’, ‘Dacron’

Repeat unit — [-OCH2CH2OOC(C6H4)CO-] n —

Eliminated water

Reaction esterification

Properties contain an ester link

can be broken down by hydrolysis
the C-O bond breaks
behaves as an ester
biodegradable

Uses fabrics
 POLYAMIDES - NYLON-6,6

Reagents hexanedioic acid HOOC(CH2)4COOH

hexane-1,6-diamine H2N(CH2)6NH2

Equation n HOOC(CH2)4COOH + n H2N(CH2)6NH2 ——> -[NH(CH2)6NHOC(CH2)4CO] n- + n H2O

Product Nylon-6,6two repeating units, each with 6 carbon atoms

Repeat unit —[-NH(CH2)6NHOC(CH2)4CO-]n—

Eliminated water

Mechanism addition-elimination

Properties contain a peptide (or amide) link

can be broken down by hydrolysis
the C-N bond breaks
behave as amides
biodegradable
can be spun into fibres for strength

Uses fibres and ropes

 PEPTIDES

Reagents amino acids

Equation H2NCCH2COOH + H2NC(CH3)COOH ——> H2NCCH2CONHHC(CH3)COOH + H2O

Product peptide (the above shows the formation of a dipeptide)

Eliminated water

Mechanism addition-elimination

Amino acids join together via an amide or peptide link

a dipeptide

2 amino acids joined dipeptide

3 amino acids joined tripeptide
many amino acids joined polypeptide
 PROTEINS

• polypeptides with large relative molecular masses (>10000)

• chains can be lined up with each other
• the C=O and N-H bonds are polar due to a difference in electronegativity
• hydrogen bonding exists between chains

dotted lines ---------- represent hydrogen bonding

 REVISION CHECK

What should you be able to do?

Recall the two main types of polymerisation

Explain and understand how alkenes undergo addition polymerisation
Work out the repeating unit in addition polymers
Recall and understand the different types of structures of poly(propene)
Recall the properties of some common polymers
Recall that polyesters and polyamides are formed by condensation polymerisation
Recall the properties and uses of some condensation polymers
Work out the repeating unit in condensation polymers
Recall that peptides are examples of condensation polymers

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 TH E
CHE MI STR Y
OF POL YME RS
THE END

© 2003 JONATHAN HOPTON & KNOCKHARDY PUBLISHING