I.

Plastics

Page 1

Topic

I.

Plastics

Reference
Reading

Chemistry A modern view Book 2 pg. 86 120

Objectives

6.1

recognise that plastics are mainly manufactured from chemicals derived from petroleum
recognise that there are different kinds of plastics
recognise that plastics are polymers built up from small molecules called monomers
recognise that alkenes, unsaturated compounds obtainable from cracking of petroleum, can undergo addition
reactions
understand that alkenes can undergo addition polymerisation
write equations for the formation of addition polymers based on given monomers or vice versa
explain the meaning of condensation polymerisation in terms of joining up molecules with the elimination of
small molecules
illustrate condensation polymerisation using block diagrams
understand the meaning of the terms 'thermosetting plastics' and 'thermoplastics'
relate the thermal properties of plastics to their usage
explain the effect of heat on thermoplastics and thermosetting plastics in terms of their structure
recognise that plastics can be moulded into articles of desired shapes
recognise that thermoplastics can be moulded more efficiently and economically than thermosetting plastics
understand the economic importance of plastics and pollution on problems associated with the use and
disposal of plastic items
recognise the importance and problems of recycling plastics

I.

Plastics

Notes

Plastics

man-made polymers which, at some stage during their processing, can be softened by heated and
then turned into any desired shape (can be moulded).

Polymer

a macromolecule formed by joining a lot of simple molecules (monomer) together.

The first plastic polythene or poly(ethene) is made by heating ethene under pressure with catalyst where ethene is
obtained from cracking of petroleum. Most of the other monomers are also derived from petroleum.

Not all the polymers are plastics. e.g. protein is a natural polymer consisted of amino acid molecules.

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Page 2
A. Different kinds of plastic

Name of
plastic

Polythene
(lighter
than water)
Polyvinyl
chloride /
PVC
(denser
than water)
Polystyrene

Perspex /
Acrylic

Thermoplastic
or
thermosetting
plastic
Thermoplastic

Thermoplastic

Thermoplastic

Thermoplastic

Speical
properties

light, low
melting point

Use

plastic bag,
bucket ()

strong but
flexible (
) if plasticizer
() is
added, toxic
monomer
strong but can be
expanded,
moderate m.p.

artificial leather
() (with
plasticizer
added) , water
pipe

Colourless and
strong

signage (),
lens ()

expanded foam
box, jelly cup

Monomer

Addition or
condensation
polymer
Addition

H H

ethene

H H

Addition

H Cl
C

vinyl chloride / chloroethene

H H

(chloroethene is poisonous)

Addition

styrene

H H

Addition

O
H C O CH3

methyl 2-methylpropenoate

H CH3

Polyester

Thermoplastic

Elastic

fibre () for
garment ()
use

dioic acid and diol

e.g.
benzene-1,4-dicarboxylic acid
O

HO C

C OH

ethane-1,2-diol
Nylon

Thermoplastic

High tensile
strength (),
light and smooth

fibre, fishing
line, socking
(), ball
bearing

UreaMethanal

Thermosetting
plastic

strong and
resistant to heat

white electric
socket, ash tray

PhenolMethanal

Thermosetting
plastic

strong and
resistant to heat

black electric
socket

Condensation
with elimination
of H2O

HO CH2CH2 OH

diamine and dioyl dichloride

H

e.g. hexane-1,6-diamine

H N

(CH2)6 N H

hexanedioyl dichloride

Cl

(CH2)4 C Cl

urea

H2N C NH2

and methanal

OH

phenol

H C

and methanal

Condensation
with elimination
of HCl

H C

Condensation
with elimination
of H2O
Condensation
with elimination
of H2O

I. Plastics

Page 3

Monomer
Ethene

Addition polymer (Formula)

Polyethene

Repeating Unit

H H

H H

H H

H H

H H

Chloroethene / Vinyl chloride

H H

Polyvinyl chloride

H Cl

H Cl

H Cl

H H

Propene

H H

Polypropene
H

C C C
H

H H

H CH3

H H

H CH3

C C

H H

methyl 2-methylpropenoate

H H

Perpex / Acrylic
O

H C O CH3

H C O CH3

H C O CH3

C C

C C

H CH3

H CH3

Styrene

Polystyrene
H

H
C

H CH3

H
C

H H

H H

Monomer
O

C O H

H H

Condensation Polymer (Formula)

Polyester

Dioic acid H O C
O H
Diol H O

O C

Repeating Unit
O

C O

O C

C O

n
H

Diamine H N

Dioyl dichloride Cl C

O H

H O

O H

C N

N C

C N

C Cl

O
H C

H O H H

H O H H

N C N C

H2N C NH2

Methanal

H O
N C

Urea-methanal

Urea

Nylon

N H

N C N C

Phenol-methanal
Phenol

OH

OH
O

Methanal

H C

OH

H
C

H
C

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Page 4
Benzene

, C6H6 is called benzene. It is an unsaturated

The structure
hydrocarbon that can be obtained from petroleum.
Indeed, it represents a ring structure with 6 carbons joining
together by alternating single and double bonds. In the drawing
of a structure containing benzene ring, H atoms on the ring are
usually omitted.

H
H

C
C

C
C

H
H

Similar to the relationship between alkane and alkyl group. A

benzene ring with a hyrogen atom removed is called a phenyl
grou

Phenyl group = benzene H atom

H

H
H

H
H

C
C

C
C

C
C

H
H

B. Polymerization
Polymerization

the process of joining together many small molecules repeatedly to form very large
molecules

There are two kinds of synthetic polymers depending on the type of polymerization reaction
Addition polymer formed by addition reaction
Condensation polymer formed by condensation reaction
Addition reaction

a reaction in which two or more molecules react to give a single molecule.

e.g. reaction between ethene and bromine.

Condensation reaction a reaction in which two or more molecules join together to form a larger molecule, with
the elimination of small molecules (e.g. H2O, NH3, HCl).
e.g. esterification reaction between alkanol and alkanoic acid.
1.

Addition reaction

Reaction between ethene and bromine

H H
C C

H H
+

Br2

H C

C H

Br Br

H H
colourless

orange

colourless

Bromine in tetrachloromethane reacts with

ethene in the absence of light and gives no
HBr. (comparing with alkane). The
orange colour of bromine is decolorized
immediately. 2 bromine atoms are added
to an ethene molecule

Reaction between ethene and KMnO4(aq)

H H
C

H H
+

H2O

+ [O]

H C C H

from oxidizing
agent KMnO4(aq)

H H

The purple colour of KMnO4(aq) is

decolorized.

OH OH
ethane-1,2-diol

purple

colourless

Reaction between ethene and hydrogen

H H
C

H H

H H
+

H2

Ni catalyst
heat, pressure

H C

C H

H H

Hydrogen can be added to the unsaturated

hydrocarbon in the presence of Ni catalyst,
heat and pressure. This is useful in
turning unsaturated lipid to more saturated
lipid. (Hydrogenation of vegetable oil to
margarine.)

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Page 5

Reaction between ethene and hydrogen chloride

The hydrogen part of HCl will favour the
C which has large no. of hydrogen on it.

H H H
H C
H H H
H C C C

major product

C C H

H Cl H
H

HCl
H H H

H C C C

minor product

H H Cl

Reaction between ethene and concentrated sulphuric acid

H H

H H H
H C

C C

(g)

+ H2SO4(l)

dH
heat

H OSO3H H

(H2SO4)

2-propyl hydrogensulphate

2.

Alkene reacts with conc. H2SO4(l) and

dissolves in it. Since the reaction is
reversible, alkene can be liberated by
heating the addition product.

Addition polymerization of alkene

A reaction in which monomer molecules join together to form polymer molecules, without elimination of small
molecules.
Similarly, under suitable conditions (heat, pressure,
catalyst), ethene can be added to another ethene
repeatedly to form a long chain polymer (with 2000
20000 C)

H H
n C

H H

H H
C

H H

H H
C

is the monomer of the polymer

H H
H H
C

H H

is the formula of the polymer, poly(ethene).

n

H H
C

is the repeating unit of the polymer.

H H

Repeating unit is the smallest part of a polymer molecule, by repetition of which the whole polymer structure
can be derived.
It is obvious that there is a direct relationship among monomer, polymer and the repeating unit.

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Preparation of polystyrene

Heating under reflux using cold finger

Heating under reflux using reflux condenser
Polystyrene can be prepared in laboratory by heating styrene with kerosene under reflux by using cold finger or
reflux condenser. The cold finger or reflux condenser condenses the vapour from the boiling liquid and prevent
escaping of vapour. This is a design used in prolonged heating of a substance.
In this example, kerosene is used as a solvent as well as a catalyst.

3. Condensation polymerization
A reaction in which monomer molecules joint together to from polymer molecules, with elimination of small
molecules (such as H2O, HCl and NH3)
Example of condensation reaction
e.g. Formation of ester (Esterification)
ester linkage
O

R C O H H O R'
alkanoic
acid

R C O
ester

alkanol

R'

An alkanoic acid molecule can react with an alkanol

molecule with elimination of water to form a
compound called ester.

+ H2O
water

e.g. Formation of peptide linkage

peptide linkage
/ amide group
O
H O C

R
C N H
H H

amino acid

O
H O C

R
C N H
H H

amino acid

O
H O C

C N C

C N H + H2O

H H

H H

dipeptide

water

Two amino acids

molecule react to
form a dipeptide with
elimination of water.

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Page 7
a) Condensation polymers
(1) Polyester
Esterification
O
HO C

C OH + HO CH2CH2 OH

O
C O CH2CH2 OH + H2O

HO C

dioic acid
diol
(benzene-1,4-dicarboxylic acid) (ethane-1,2-diol)

Similar to formation of ester, A dioic acid and a diol condenses together with elimination of water molecule to
form an ester molecules. Since each monomer has two function groups, it is capable to condense repeatedly to
form a very long chain polymer.

The trade name of the polyester ester formed by benzene-1,4-dicarboxylic acid and ethane-1,2-diol is called
Terylene.

(2) Nylon
Similar to dipeptide formation, a diamine is capable to react with a dioyl dichloride to form a peptide linkage
(amide group) with elimination of a HCl molecule. Since each monomer contains two functional group, the
product is capable to undergo successive condensation and a long polymer molecule (nylon) would be formed.
H
H N

H
(CH2)6 N H + Cl

diamine
(hexane-1,6-diamine)

(CH2)4 C

H
Cl

dioyl dichloride
(hexanedioyl dichloride)

H O

H N

(CH2)6 N C

O
(CH2)4 C Cl + HCl

peptide linkage
/ amide group

The nylon formed by hexane-1,6-diamine and hexanedioyl dichloride is called nylon 6.6. The first 6 indicates
the no. of C in the diamine and the second 6 indicates the no. of C in the dioyl dichloride.
In industrial preparation of nylon 6.6, hexane-1,6-dioic acid is used instead of hexanedioyl dichloride with
elimination of H2O. This is because the former one is cheaper.

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(3) Urea-methanal
Preparation of urea-methanal involves two steps:

i. formation of long chain molecule

ii. formation of cross-link between chains

Formation of long chain molecule

O

Urea H2N C NH2 and methanal H C H are heated with a little conc. H2SO4(l). The urea condenses with methanal
repeatedly to form a long chain molecule.

Formation of cross-link between chains

Upon further heating, cross links
are formed between the long chains.
This results in a hard, rigid giant
network similar to diamond and
silicon(IV) oxide. This is normally
done in the moulding process.
The cross-link capable monomer
has more than 2 reaction sites for
reaction to take place.

(4) Phenol-methanal (a thermosetting plastic)

OH

Formation of phenol-methanal is similar to urea-methanal using phenol

instead of urea H2N C NH2 . The
properties of phenol-methanal is similar to that of urea-methanal, except that phenol-methanal is black in colour
while urea-methanal is white.
Formation of long chain molecule
- H2O

- H2O

OH

OH
H

OH
H

H C H
H

H
H

OH
H

H C H
H

H
H

H
H

repeated
condensation

H
C
H

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Page 9
Formation of cross-link between chains
OH

OH

H
C

H
HH

H
HH

H
H

H C

H C H
HH
H

H
H

cross-link

OH

HH
H

C
OH

condensation with
elimination of water

OH

C
H

OH

C O -H O C O
- H2O
2
H
H
H
H
H
HH
HH
H
H

OH

OH

H
H

H
HH
H

H
C

H
HH

OH

OH

OH

C
OH

Comparing the monomers of thermoplastics with monomers of a themosetting plastics, only monomers with more
O

than 2 reactioin sites can form thermosetting plastics. e.g. 4 reaction sites in urea H2N C NH2 and 3 reaction
OH
sites in phenol
. This is because monomers with 2 reaction sites only will only be able to form a linear
chain.

C. Thermal properties of thermoplastic and thermosetting plastic

Thermoplastic a plastic which can be softened by heating and hardened by cooling. The process can be
repeatable any number of time.
Thermosetting plastic a plastic which, once set hard, cannot be softened again by heat.

Structure of thermoplastic in the solid state

Giant network structure of thermosetting plastic

The cross-link among the chains in thermosetting plastic make it resistant to heat. If a thermosetting plastic is
heated strongly in air, it will char and decompose.

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Decomposition of plastic
The action of heat on plastic is depending on several factors
1) Structure of the polymer
2) Strength of heating
3) Availability of air

1) Structure of the polymer

Depending on the availability of cross links among the polymer chains, thermoplastic softens upon gentle heating
while thermosetting plastic does not. This is because the attraction among the thermoplastic polymer molecules
are only weak van der Waals' forces and would be weakened by heat easily. On another side, the attraction among
the thermosetting plastic molecule chains are strong covalent bond. i.e. cross link. As a result thermosetting does
not soften upon gentle heating.
2) Strength of heating
If the temperature is not really high, thermoplastic will be softened upon heating while thermosetting plastic will
not. However, if the heating is really strong, strong enough to break the covalent bond, both thermoplastic and
thermosetting plastic will decompose.
3) Availability of air
In the presence of air, most polymers will burn at high temperature, since all polymers are basically long carbon
chain like alkane.
In general, the carbon atoms (C) will be converted to carbon dioxide CO2(g).
the hydrogen atoms (H) will be converted to water vapour H2O(g).
the chlorine atoms (Cl) will be converted to hydrogen chloride molecules HCl(g).
the nitrogen atoms (N) will be converted to ammonia NH3(g) or hydrogen cyanide HCN(g).
However, in the absence of air, difference polymers will decompose to different products at different temperature.
For example, some polymer will undergo depolymerization and be converted back to the monomers but some
polymers will just decompose to simple molecules (e.g. alkane and alkene) like in cracking of long hydrocarbon
chain.

Depolymerization of perspex
Perspex methyl 2-methylpropenoate
depolymerization

Upon heating, perspex will soften, melt, fume and char. The monomer vapour will be condensed in the receiving
test tube by the ice-water mixture. Since the vapour evolved is toxic, this experiment must be carried out in the
fume cupboard.
N.B.
Depolymerization is a decomposition process. Besides the monomers, many other products may also be
obtained, including carbon (charcoal), (carbon monoxide and carbon dioxide if the polymer contains oxygen),
water and other organic compounds since it is a random process.

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Page 11
D. Moulding of plastic
1.
2.

Add required additives e.g. plasticizer, colour pigment

Mould into desired shape by heat.

1. Moulding of thermoplastic
e.g. Injection moulding

Plastic granules of thermoplastic (e.g. poly(ethene)) is heated until molten. The molten plastic is injected into the
mould and cooled by running water. The plastic article is hardened and removed from the mould.
2. Moulding of thermosetting plastic
e.g. Compression moulding

Moulding powder (e.g. urea-methanal) with no cross-link between the chains is put into the mould. The powder
is compressed and heated. Cross-link is formed upon heating and the plastic hardens.
3.

Efficiency of moulding process

Thermoplastic article is hardened by cooling but thermosetting plastic article is hardened by heating (heat
curing). Therefore, thermosetting plastic cannot be kept in molten state.
Injection moulding is relatively faster than compression moulding. In injection moulding, the molten plastic
can be injected into the mould continuously. The time to make each plastic article is rather short.
In compression moulding, moulding powder has to be put into the mould batch by batch. Furthermore, a
longer time is required for the formation of the cross-links.
Thus, thermoplastics can be moulded more efficiently and economically than thermosetting plastics.

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Page 12
E. Economic importance and problem of using plastic
1.
1.
2.
3.
4.
5.
6.

Advantages of using plastic

Cheap
Can be moulded into any shape easily
Chemically inert, i.e. no reaction with air, water, acid, alkalis etc.
Strong but light
Good insulator of heat and electricity
Some of them are flexible

2.
1.

Problem of using plastic

Land pollution plastic is non-biodegradable and is usually buried in landfill. They take a very long time to
decompose in nature.
Air pollution upon burning in the incinerator, toxic gas may evolve. In order to reduce the amount of
toxic gas emitted to the atmosphere, a scrubber may be installed to remove the soluble gases
e.g. HCl and NH3, electrostatic precipitator to remove the soot.

2.

3.
1.
2.
3.

Remedies
Use less plastic Use less plastic bag as promoted in BYOB (Bring Your Own Bag) campaign
Re-use of plastic scrap the scrap produced during moulding of plastic is melted and reused.
Recycling of plastic the plastic waste is collected and sorted according to the type of plastic. They are
washed, melted and remoulded into new plastic article. The job is labour intensive and
the recycled products are usually with low value.
Reasons of recycling :

1. to save raw materials

2. to reduce plastic wastes which are non-biodegradable.
Problems associated with recycling of plastics :
1. Difficult to separate different plastics
2. Removal of additives in plastics
3. Economic considerations
4.
5.
5.

As fuel in power station this may cause air pollution.

Making biodegradable plastic
Pyrolysis Decomposition or
transformation of a compound
caused by heat.

Plastic is heated in the absence

of air at about 700C

The plastic molecules would

break down to form smaller
molecules, e.g. methane,
ethene, propene and benzene.

The products can be separated

by fractional distillation and
eused.

Unlike recycling of plastic,

pyrolysis does not require
sorting of various types of
plastic.

At present, the process is still at

an experimental stage and still
have to prove its economic
viability.

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Page 13

Glossary

plastic
polymer
monomer
addition polymerization
condensation polymerization
repeating unit
depolymerization
esterification
Terylene
cross-link
thermoplastic
thermosetting plastic / thermoset
plasticizer
injection moulding
compression moulding
moulding powder
non-biodegradable
pyrolysis

Past Paper
`Questions

91 I 2 b i ii
92 I 4 a i
93 I 1 c iv
94 I 3 a b c d i ii
95 I 2 b
96 I 7 b i ii iii iv v
97 I 1 c
98 I 2 a
99 I 1 i ii
2000 I 7 b i ii iii iv

91 I 3 a iv
93 I 2 a i
95 I 6 a iv
97 I 7 b i ii
98 I 7 a iii
99 I 9 b ii iv v

98 I 7 b i ii iii

91 I 2 b i ii
2b
The following diagrams show three plastic items. The universal adaptor is made of thermosetting plastic while
the other two are made of thermoplastics.

i
ii

Explain why thermoplastics are not suitable for making universal adaptors.
1
It softens (melts) by heat / it burns quite easily
1 mark
The foam lunch box is made from a plastic containing a trapped gas. Name the plastic that is commonly used and 2
state the purpose of trapping a gas within the plastic.
+Polystyrene / poly(phenylethene) / polyphenylethene
1 mark
(+Correct spelling is required.)
Making the plastic a better insulator of heat.
1 mark

91 I 3 a iv
3a
Petroleum, often referred to as a 'fossil' fuel, can be separated into various fractions by fractional distillation. The
following table shows the annual production and consumption of petroleum fractions in a certain country.
Petroleum fraction
Annual production (in million tonnes)
Annual consumption ( in million tonnes)
Petrol
10
25
Naphtha
5
5
Kerosene
20
20
Diesel oil
15
35
Heavy oil
40
5
Liquefied petroleum gas
6
4
iv A sample of liquefied petroleum gas is known to contain propene and propane.
9
(1) Draw the structural formula of
(I) propene, and
(II) propane.
(2) (I) Write the equation for the complete combustion of propane in air.
(II) Explain whether the combustion of propene or propane would produce a more sooty flame.
(3) How would you show that propane consists of
(I) carbon, and
(II) hydrogen ?
(4) Apart from combustion, describe another chemical test to distinguish propene from propane.

I. Plastics

Page 14

(1) (I)

(II)

H H H
H C C C

H / CH3CH CH3

H H H
H C C C

H / CH3CH2CH3

H H H

1 + 1 marks

(N.B.: hydrogen must be shown.)

1 mark
(2) (I) C3H8 + 5O2 3CO2 + 4H2O
(II) propene burns with a more sooty flame because its C : H ratio is higher / it has a higher carbon content.
( N.B.: Do not accept propene is unsaturated. )
1 mark
1 mark
(3) Combustion of / burn propane gas in oxygen (air) / pass propane over strongly heated CuO.
(I) Gaseous product / CO2 turned lime water milky proves the presence of carbon in the compounds.
1 mark
(II) Colourless liquid / H2O after combustion turned anhydrous copper(II) sulphate blue / cobalt(II) chloride
paper pink proves the presence of hydrogen in the compound
1 mark
(4) Either of the following tests:
Observation
Test
Propene
Propane
decolourizes it quickly
decolourizes it slowly
Adding bromine water
or decolourizes it
or does not decolourizes it
or bromine in CCl4 / 1,1,1-trichloroethane
(Do not accept Br2(g))
decolourizes it
does not decolourize it
Adding acidified MnO4-( MnO4- / H+ )
(N.B.: 1 mark for test, 1 mark for both observations.)
2 marks
[Do not accept passing propene and propane through conc. sulphuric acid.]
(2) (II) Most candidates wrongly indicated that propene burns with a more sooty flame simply because it was
unsaturated.
(3) While most students were aware that carbon dioxide and water are formed when propane burns in oxygen or
air, many did not suggest chemical tests for these two combustion products in order to show the presence of
carbon and hydrogen in propane.
(4) Some candidates suggested using bromine gas to distinguish propene from propane instead of using
Br2/CCl4. A number of the candidates even thought that propene could decolorise potassium permanganate
solution which had not been acidified.

92 I 4 a i
4a i
The structure of polymer X can be represented by the following diagram:

represents a group containing carbon and hydrogen atoms only.

where
(1) Draw the structure of the monomer of X.
(2) Name an example of a polymer with the structure of X.
(3) Two separate pieces of X are strongly heated as shown in diagrams A and B below:

What would be observed in each case ? Explain your answer.

(1)

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Page 15
H
C

H H

1 mark
(2) Polypropene / Polystyrene / Polyphenylethene
1 mark
[Correct spelling is required. Accept other answers in which the monomers are RCH=CH2.]
1 mark
(3) Case A: the polymer melts / softens inside the test tube
because polymer X is a thermoplastic.
1 mark
OR
the polymer fumes
(1 mark)
because the polymer breaks down / decomposes / depolymerizes when heated in a limited supply of
air.
(1 mark)
Case B: the polymer melts and burns / chars / flames
1 mark
because there is enough supply of oxygen / air for the polymer to burn / char.
1 mark
(3) This part was intended to test candidates' knowledge of the action of heat on a thermoplastic under 2
different experimental conditions (i.e. Case A with a limited supply of air and Case B with a plentiful supply
of air). Few candidates were able to describe and explain the observations correctly.

93 I 1 c iv
1c
Alkenes can be obtained from petroleum fractions by a process called 'cracking'. Using a suitable petroleum
fraction, a student carried out this process in the laboratory and collected the gaseous product over water.
iv If the gaseous product decolorizes a solution of bromine in tetrachloromethane, can you conclude that the
gaseous product is ethene ? Explain your answer.
No, all compounds with C=C or CC bonds / all unsaturated / hydrocarbons / all alkene can decolourize
bromine. (Do not accept substitution of alkanes)
2 or 0 marks
93 I 2 a i
2a
Tuning knobs on radios are often made of plastics plated with metal coatings.
(Faraday constant = 96500 C mol-1. Relative atomic mass of nickel, Ni = 58.7)
i
State TWO reasons why plastics are used in the manufacture of tuning knobs.
easy shaping / low cost / light weight / resist corrosion (unreactive) (any 2)

2
1 + 1 marks

94 I 3 a b c d i ii
3
The following diagrams show some items made of synthetic polymers.

3a

3b

3c
C
3d
i

ii

Which of the above items is most likely to be made of thermosetting plastics ? Explain your answer.
Electric switch
1 mark
1 mark
The plastic used should be heat resistant / should not soften / melt at high temperatures.
Name one synthetic polymer which is suitable for making the plastic bag.
Polyethene (polythene) / polypropene (polypropylene) / polychloroethene (polyvinyl chloride) / nylon 1 mark
(Correct spelling is required. Do NOT accept polystyrene / perspex / short form, e.g. PE, PP, PVC etc.)
Suggest a suitable moulding method used in making the electric switch.
Compression (moulding)
1 mark
Many candidates could not suggest the correct moulding method for making the electric switch.
Terylene, the polyester fibre used for making the shirt is synthesized from ethane-1,2-diol, HOCH2CH2OH and
benzene-1,4-dicarboxylic acid, HOOCC6H4COOH.
Name the type of polymerization involved in the synthesis of terylene.
Condensation (polymerization)
1 mark
(Correct spelling is required.)
Write a repeating unit of terylene.
O

(OCH2CH2OCOC6H4CO)

or

CC6H4C OCH2CH2O

1 mark

1
1

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[Do NOT accept (OCH2CH2OCOC6H4CO)n]

Page 16

95 I 2 b
2
In each of the following groups of substances, there is ONE substance which is different from the others in terms
of their properties. In each group, identify the substance which is different from the others and explain your
choice.
2b
nylon, perspex, polyethene, urea-methanal
2
Urea-methanal
1 mark
It is a thermosetting plastic (cannot by softened by heat)
1 mark
or, the other substances are thermoplastics (can be softened by heat)
C
Candidates were asked to identify the one substance which is different from the others and to explain the
difference in terms of their properties However, many candidates overlooked the word 'properties' in the question.
Some candidates gave wrong reasons for the correct choice, urea-methanal. They thought that it was the only
condensation polymer.
95 I 6 a iv
6a
The illustration below shows the plastic bottle of a domestic toilet cleaner and its label.

iv

(1) Explain why plastic is used for making the bottle for the toilet cleaner.
(2) Name ONE plastic material suitable for making the bottle for the toilet cleaner.
(1) It is inert / does not react with HCl / the bottle is not easily broken / flexible / light in weight / can be
moulded easily.
1 mark
(2) Polyethene / polythene / polypropene / polystyrene / polyvinyl chloride etc.
1 mark
(Correct spelling is required)
(Do not accept short forms e.g. PE, PP, PS...)
(Do not accept perspex / name of any thermosetting plastics)
(1) Many candidates wrongly used the term 'resistance to corrosion' or 'corrosion resistant' for the
unreactive/inert property of plastics.
(2) A number of candidates wrongly gave 'urea-methanal' or 'perspex' as the answer for the plastic material.

96 I 7 b i ii iii iv v
7b
The flow diagram below shows the three key stages involved in the production of polypropene bottles from crude
oil.

i
ii

What is the process involved in obtaining heavy oil from crude oil in Stage I ?
fractional distillation of crude oil
(1) Draw the structure of monomer A .

1
1 mark
3

I. Plastics
(2) What are the TWO main processes involved in the production of monomer A from heavy oil in Stage II ?
(1)

CH3

/ CH3CH CH2

C C
H

Page 17

(2) (catalytic) cracking of heavy oil

separation / fractional distillation of the mixture to obtain propene
(1) Some candidates drew the following wrong structure for monomer A:

1 mark
1 mark
1 mark

H H H
H C C

C H

H H

iii What are the TWO main processes involved in the production of polypropene bottles from monomer A in Stage
2
III ?
Monomer A (propene) is polymerised to give polypropene
1 mark
1 mark
polypropene is moulded / blow-moulded / injection moulded to give the polypropene bottle
Many candidates suggested various methods of moulding, such as injection moulding, blow moulding, vacuum
moulding and extrusion moulding. In fact, the names and details of the method of moulding are not required by
the syllabus.
iv Suggest ONE reason why the disposal of polypropene wastes can cause pollution problems.
1
Polypropene cannot be easily degraded by micro-organisms / the degradation of PP takes a long time / PP is nonbiodegradable
1 mark
or, the incineration / burning of PP waste may produce toxic eases /air pollutants
v Polypropene wastes can be recycled by melting and remoulding.
2
(1) What preliminary treatment of the polypropene wastes is required before recycling ?
(2) Name ONE plastic which cannot be recycled by melting and remoulding.
(1) Separating PP from other plastic wastes / cleaning the PP wastes
1 mark
(2) *Urea-methanal (accept correct name of any thermosetting plastics e.g. *phenol-methanal, *bakelite)
* correct spelling is required.
1 mark
(1) Some candidates suggested incorrect answers such as removing additives / dyes / plasticizers from the plastic
wastes.
(2) Most candidates wrongly spelt the name of the thermosetting plastic, urea-methanal, as 'urea-methanol'.

97 I 1 c
1
For each of the tasks listed in the table below, decide which substance on the right is the best to use to accomplish
the task. Explain your answer in each case.
For each of the following, award 1 mark for the correct choice and 2 marks for the explanation; (must involve a
sense of comparison); disregard the explanation for a wrong choice. i.e. zero mark is given to a wrong choice.
Task
Substance
polyethene, polystyrene,
3
1c
To make feeding bottles for babies
urea- methanal

polystyrene
Feeding bottles are usually sterilized by heating in boiling water, polyethene has a low m.p. / cannot withstand
the temperature of boiling water / deforms at the temperature of boiling water
Urea-methanal. It cannot be moulded into the shape of a bottle / is not transparent.
(DO NOT accept urea-methanal is a thermosetting plastic alone.)
In (c), many candidates wrongly chose urea-methanal, the only thermosetting plastic. They failed to consider the
fact that the substance used for making feeding bottles should be transparent and be able to withstand the
temperature of boiling water.

97 I 7 b i ii
7b
The structures of five compounds, I, II, III, IV and V, are shown below:

I. Plastics

Page 18

represents a saturated hydrocarbon chain containing 1 to 6 carbon atoms and

In the above structures.
represents a saturated hydrocarbon chain containing 12 to 20 carbon atoms.
Which compound can be used to make an addition polymer ? Write a chemical equation to represent the addition 2
polymerization.

IV /

1 mark

1 mark
C
ii

incorrect chemical equation for the addition polymerization;

Which TWO compounds can be used to make a condensation polymer ? Draw the repeating unit of the polymer
formed.
II and III
1 mark

1 mark
C

incorrect repeating unit for the condensation polymer;

98 I 2 a
2
For each of the following experiments, state the expected observation and write a relevant chemical equation.
2a
Ethene is passed into an acidified potassium permanganate solution.
Potassium permanganate solution changes from purple to colourless
/ purple colour of potassium permanganate fades.
1 mark
=CH2 + [O] + H2O CH2(OH)CH2(OH)
1 mark
CH2
(1 mark)
or, 5 CH2=CH2 + 2H2O + 2MnO4- + 6H+ 5CH2(OH)CH2(OH) + 2 Mn2+
(Also accept equations showing further oxidation of ethane-1,2-diol to ethanedioic acid /
carbon dioxide. Do NOT accept half equations.)

98 I 7 a iii
7a
Both carbon and silicon are Group IV elements in the Periodic Table. The diagrams below show the structures of
dry ice (solid carbon dioxide) and quartz (a form of silicon dioxide):

iii Sand (an impure form of quartz) and limestone are raw materials used for making glass.
(1) Name the main chemical constituent of limestone.

I. Plastics
(2)
(3)
(1)
(2)
or,
(3)

Page 19

Suggest ONE reason why glass had been used by mankind for a long time.
Suggest ONE reason why glass bottles are preferred to plastic bottles for the storage of champagne.
calcium carbonate
1 mark
the materials for making glass are easily available / abundant in the earth crust.
1 mark
Glass can easily manufactured by heating sand, limestone and sodium hydroxide.
(1 mark)
champagne contains a pressurized carbon dioxide solution.
Glass can withstand the pressure.
1 mark
or, the ethanol solution (champagne) can dissolve unpolymerized monomers in plastic
(1 mark)
Part (3) was poorly answered. Many candidates did not realize that champagne contains a pressurized carbon
dioxide solution and that glass bottles, which are much stronger than plastics bottles, are used for the storage of
champagne.

98 I 7 b i ii iii
7b
Polyvinyl chloride (PVC) is a plastic which has a wide range of uses.
i
Write the chemical equation for the formation of PVC from its monomers.

n CH2 = CHCl

1
n

1 mark
Plastic products made of PVC may vary greatly in rigidity.
3
(1) Give ONE flexible product made of PVC.
(2) Give ONE rigid product made of PVC.
(3) Explain whether PVC is suitable for making electric sockets or not.
(For (1) and (2), accept other correct uses of PVC)
(1) garment / surface of sofa / hose / cable sheathing / foot wear / tiles / curtains / rain coats / bottles 1 mark
(2) pipes / bottles / record
1 mark
(3) No. PVC is a thermoplastic / melts upon heating.
1 mark
5
iii Incineration of PVC wastes produces hydrogen chloride which causes air pollution.
(1) State ONE harmful effect of the discharge of hydrogen chloride into the atmosphere.
(2) Suggest how hydrogen chloride can be removed from incinerator flue gas prior to its discharge to the
atmosphere.
(3) Suppose that all the chlorine in PVC is converted to hydrogen chloride upon incineration. Calculate the
volume of hydrogen chloride produced, measured at room temperature and pressure, when a plastic waste
containing 1000 kg of PVC is incinerated.
(You may assume that no other chlorine containing compounds are present in the waste.)
(Relative atomic masses: H = 1.0, C =12.0, Cl = 35.5;
molar volume of gas at room temperature and pressure = 24.0 dm3)
(1) acid rain / damage to the respiratory system
1 mark
(2) washing the flue gas with alkali / water
1 mark
or, pass flue gas through scrubber
(1 mark)
(3) No. of moles of HCl produced = no. of moles of PVC repeating units
1 mark
= 100000 / (12 2 + 1 3 + 35.5)
(1 mark)
= 16000
(1 mark)
Volume of HCl produced = 16000 24
(step mark)
1 mark
= 384000 dm3
1 mark
In part (3), many candidates did not realize that the number of moles of HCl liberated equals the number of
moles of PVC repeating units and hence they did not arrive at the correct answer. It is necessary to point out that
the scenario described in the question is a hypothetical one and that incineration of PVC wastes produces a
number of air pollutants other than HCl.
ii

CH2CHCl

99 I 1 i ii
99 I 9 b ii iv v
2000 7 b i ii iii iv

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Page 20

1990 36
6 C 36 Which of the following tests can be used to distinguish between ethane and ethene?
(1) burning the gas in air
(2) bubbling the gas through bromine in tetrachloromethane
(3) bubbling the gas through acidified potassium permanganate solution
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
1990 41
6 A 41 Which of the following polymers is/are made by condensation polymerization ?
OH

H
C

(1)

n
OH

H
C

(2)

H COOCH3
C

(3)
A.
B.
C.
D.

H CH3

(1) only
(3) only
(1) and (2) only
(2) and (3) only

1991 22
6 C 22 Propene reacts with acidified potassium permanganate solution to form
A. CH3CH2CH2OH.
B. CH3CH(OH)CH3.
C. CH3CH(OH)CH2OH.
D. CH2OHCH(OH)CH2OH.
1991 26
6 D 26 Teflon, a polymer used for coating non-stick cooking utensils, has the structure give below :

Which of the following is the monomer for Teflon ?

A. 1,2-difluoroethane
B. 1,2-difluoroethene
C. 1,1,2,2-tetrafluoroethane
D. 1,1,2,2-tetrafluoroethene
1991 27
6 D 27 A sample of polymer gives acid fumes on strong heating. The polymer is probably
A. nylon.
B. polypropene.
C. polystyrene.
D. polyvinyl chloride.
1991 40
6 C 40 Which of the following compounds would react with each other to form a condensation polymer ?
H

(1)

H
C

C
H

(2)

HO C

(3)

H2N C NH2

(CH2)4 C OH

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Page 21
(4)
A.
B.
C.
D.

H2N

(CH2)6 NH2

(1) and (2)

(1) and (3)
(2) and (4)
(3) and (4)

1992 21
6 A 21 When 2-methylpropene reacts with bromine in tetrachloromethane, the product is

C.

Br

CH3 H
C

Br

Br

CH3 H

Br

B.

A.

CH3 H

Br

D.

H C

Br

CH3 H

H C
Br

Br

1992 25
6 A 25

O
C

The polymer formed by H2N(CH2)6NH2 and

H

A. has a formula of

H O
(CH2)6 N C

(CH2)4 C

OH

HO

(CH2)4 C

B. is a thermosetting plastic.
C. has cross-linkages.
D. burns with a floral smell.
1992 43
6 C 43 Which of the following polymers is/are NOT suitable for making a container for boiling water ?
(1) perspex
(2) urea-methanal
(3) polyvinyl chloride
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
1992 47
T t
47 Polyester is a thermoplastic.

Polyester is formed by condensation polymerization.

1993 34
6 A 34 When concentrated sulphuric acid is added dropwise to a solution containing urea and methanal in a test tube with
shaking, a white solid can be formed. Which of the following statements about this experiment is/are correct.
(1) The reaction involved is condensation polymerization.
(2) Concentrated sulphuric acid acts as an oxidizing agent.
(3) The white solid is a thermoplastic substance.
A. (1) only
B. (3) only
C. (1) and (2) only
D. (2) and (3) only
1993 35
6 C 35 A polymer has the following structure :

Its monomer is

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Page 22
A.
B.
C.
D.

chloroethene.
1,1-dichloroethane.
1,2-dichloroethene.
1,2-dichloroethane

1994 41
6 D 41 A compound has the following structure :

H
C

CH3CH2

C
H

Which of the following statements about this compound are

correct ?
(1) It can decolorize bromine water.
(2) It can be polymerized.
(3) It can burn in air.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
1995 20
B 20 Which of the following statements concerning alkenes is
INCORRECT ?
A. They can decolorize a solution of bromine in 1,1,1trichloroethane.
B. They can decolorize red litmus solution.
C. They can decolorize acidified potassium permanganate
solution.
D. They can be polymerized to form addition polymers.
1995 22
C 22 The formula below can be used to represent the structure of
some polymers.
H H H H
C C

C C

H X H X

(X represents an atom or a group of atoms.)

Which of the following combinations is INCORRECT ?
X
Name of polymer
A. H
polyethene
B. Cl
polyvinyl chloride
perspex
C. CH3
polystyrene
D. C6H5
1995 36
D 36 Which of the following statements concerning ureamethanal is/are correct ?
(1) It softens on gentle heating.
(2) It can be used to make ash trays.
(3) It consists of polymer chains with cross-linkages
between the chains.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
1995 41
D 41 Which of the following statements concerning the recycling
of plastics are correct ?
(1) The recycling of plastics can help to solve the disposal

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Page 23
(2)
(3)
A.
B.
C.
D.

problem of plastics.
The recycling of plastics can save raw materials derived
from petroleum.
It is difficult to separate different types of plastics in the
recycling process.
(1) and (2) only
(1) and (3) only
(2) and (3) only
(1), (2) and (3)

1995 47
T t
47 Nylon softens on heating.
1996 5
B 5

Which of the following materials are suitable for making

the base and handle of a frying pan ?
Base
Handle
A. aluminium polyvinyl chloride
B. copper
urea-methanal
C. titanium
polyvinyl chloride
D. zinc
urea-methanal

1996 34
C 34 Which of the following statements concerning nylon and
urea-methanal is/are correct ?
(l) They are formed by condensation polymerization.
(2) They have cross-linkages between polymer chains.
(3) They are nitrogen-containing compounds.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
1997 18
A 18 The model. shown below represents a compound containing
6 hydrogen atoms (white spheres) and 3 carbon atoms
(black spheres).

Which of the following statements concerning the

compound is INCORRECT ?
A. Its structural formula is C3H6.
B. It can be prepared by cracking petroleum fractions.
C. It can decolorize bromine in 1,1,1-trichloroethane.
D. It can undergo polymerization.
1997 33
D 33 Which of the following statements concerning the reaction
of methane with bromine is/are correct ?
(1) It is an addition reaction.
(2) It is a substitution reaction.
(3) A similar reaction will occur if propane is used instead
of methane.
A. (1) only
B. (2) only

Nylon is a condensation polymer.

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Page 24
C. (1) and (3) only
D. (2) and (3) only

1997 40
A 40 Which of the following methods can be used to solve the
pollution problems associated with the disposal of plastic
waste ?
(1) recycling of plastics
(2) making biodegradable plastics
(3) burning plastic waste in incinerators with tall chimneys
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
1998 24
D 24 Consider the following manufacturing process:

Which of the following graphs (not drawn to scale) can

represent the change in relative molecular masses of the
substances involved during the manufacturing process ?

1998 36
D 36 Which of the following statements concerning polystyrene
is/are correct ?
(1) It is a condensation polymer.
(2) It can be remoulded.
(3) It can be used to make packaging material for electrical
appliances.
A. (1) only
B. (2) only

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Page 25
C. (1) and (3) only
D. (2) and (3) only

1998 49
T t
49 Wash bottles used in the chemistry laboratory are
commonly made of polyethene.
1999 28
A 28 Which of the following substances is a thermoplastic as well
as a
condensation polymer ?
A. nylon
B. perspex
C. polyethene
D. urea-methanal
1999 32
C 32 Which of the following substances can react with acidified
potassium permanganate solution ?
(1) ethene
(2) copper(II) sulphate solution
(3) iron(II) sulphate solution
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
1999 41
B 41 Plastic X has the following structure:

Which of the following statements concerning X are

correct ?
(1) The monomer of X is CHCl=CHCl.
(2) X can be used to make electric sockets.
(3) The flue gas produced by the incineration of X can
cause the formation of acid rain.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
2000 15
C 15 A polymer has the following structure:

What is the monomer of this polymer ?

A. butane
B. but-l-ene
C. but-2-ene
D. 2-methylpropene
2000 32
D 32 Which of the following articles should be made from
thermosetting plastics ?
(1) wall paper
(2) television casing
(3) water bucket

Polyethene is an addition polymer.

I. Plastics

Page 26
A.
B.
C.
D.

(1) only
(2) only
(1) and (3) only
(2) and (3) only

2000 36
A 36 Which of the following polymers is/are made by
condensation polymerization ?

A.
B.
C.
D.

(1) only
(2) only
(1) and (3) only
(2) and (3) only

2000 38
A 38

Some concentrated sulphuric acid was poured into a sink

connected to a catchpot made of polyvinyl chloride (PVC).
After some time, the catchpot became deformed. Which of
the following explanations for the deformation of the
catchpot is/are correct ?
(1) The heat liberated when the concentrated sulphuric
acid mixed with the water in the catchpot caused PVC
to soften.:
(2) PVC was decomposed into its monomers by the
concentrated sulphuric acid.
(3) PVC was oxidized by the concentrated sulphuric acid.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only