Addition Polymer

Topic 7 Fossil Fuels and Carbon Compounds
Unit 28 Addition polymers
Jing Kung Educational Press All Rights Reserved

Unit 28 Addition polymers 2
Content
28.1 Synthetic polymers all around you
28.2 Why are synthetic polymers so useful?

28.3 Addition polymerisation of ethene
28.4 Making other synthetic polymers
28.5 Uses of some common addition polymers
Continued on next page

Content
Key terms
Summary
Unit Exercise
Topic Exercise

28.1 Synthetic polymers all around you (p.136)

w Almost everywhere you look, you will see objects made of
plastic (塑膠).
w Plastics are examples of what chemists call synthetic
polymers (合成聚合物).
w A polymer (聚合物) is a
compound consisting of very large
molecules formed by joining
together many small molecules
repeatedly.

28.2 Why are synthetic polymers so useful?

(p.138)
Synthetic polymers have many advantages. In general , they’re
w lightweight;
w resistant to chemicals;
w strong;
w good thermal and electrical insulators;
w waterproof;
w can be easily moulded into different shapes;
w can be easily coloured;
w cost-effective.

28.3 Addition polymerisation of ethene (p.139)

w The alkenes obtained from catalytic cracking of petroleum
fractions are the starting compounds for making many
common synthetic polymers.
w Part of C=C bond of each molecule breaks; other atoms add on.
w The two electrons of C=C may be used to join neighbouring
ethene molecules to make a long chain of polymer polythene.


w This type of reaction is called addition polymerisation (加成
聚合作用)—one in which monomer molecules join together
repeatedly to form polymer molecules. No atoms are lost from
the monomer molecules during the reaction.
w High temperature / high pressure / catalyst is used for
addition polymerisation.
w Polythene is an addition polymer (加成聚合物). The ‘ene’
ending is still used even though the polymer is saturated.


w The polymerisation of ethene can be shown by the equation
below:
w The section inside the bracket is the repeating unit (重複單位):

w A repeating unit is the smallest part of a
polymer molecule, and the whole polymer
molecule can be obtained by repeating it.
w n is often several thousands


Below are some features of addition polymers and addition
polymerisation:
w Polymers consist of long-chain molecules formed by joining
many monomer molecules together.
w Monomer molecules containing carbon-carbon double
bonds can undergo addition polymerisation to give addition
polymers.
w During addition polymerisation, part of the double bond of
each monomer molecule is broken, and the molecule joins
to neighbouring monomer molecules to make a molecule
with a very long chain.


Two common types of polythene:
w low density polythene, LDPE (低密度聚乙烯)—
heating ethene at high pressures and high temp. with
initiator (引發劑) (often peroxides);
w high density polythene, HDPE (高密度聚乙烯)—
manufactured at relatively low pressures and low
temperatures with a special catalyst.

28.4 Making other synthetic polymers (p.142)

w Many other polymers can be made from monomers
containing C=C bonds, but NOT from benzene.



Deducing the structure of an addition polymer


Deducing the structure of a monomer


Q (Example 28.1)
Polymer B shown below can be formed
from the polymerisation of compound A.
a) Write the structural formula of compound A and give its systematic name.
b) State the type of polymerisation for the formation of B from A.
c) Suggest why the relative molecular mass of B is expressed using a range of
values instead of a single fixed value.
A
a)
b) Addition polymerisation
c) B is a mixture of polymeric molecules with different lengths.


Practice 28.1
1 Compound X can form a polymer with the structure shown below.
a) Draw the repeating unit of the polymer.

b) Write the structural formula of compound X and state its systematic name.


2 Compound A shown below can polymerise to form an addition polymer.
a) State the systematic name of compound A. Propenoic acid

b) Write the chemical equation for the polymerisation of compound A.

28.5 Uses of some common addition

polymers (p.145)
w Polymers have different uses as they have different properties.
Structure of LDPE Structure of HDPE

- shorter average chain length - longer average chain length
- highly branched - not highly branched


polymers (p.145)


polymers (p.145)


polymers (p.145)


polymers (p.145)


polymers (p.145)


polymers (p.145)
Preparing polystyrene Investigating the properties of

some polymers


polymers (p.145)
Q (Example 28.2)
Polythene can be used to make food wrap.
a) Explain, in terms of bonding, why objects made of polythene are resistant to
chemical attacks.
b) Explain why ethene can form a polymer, but ethane CANNOT.
c) 'Saran' can also be used to make food wrap. A section of a polymer chain of
'Saran' is shown below.
i) In terms of intermolecular forces, explain why 'Saran' is more suitable

than polythene in making food wrap for use in microwave ovens.
ii) Incineration of 'Saran' waste produces hydrogen chloride which causes
air pollution. State ONE harmful effect of the discharge of hydrogen
chloride into the atmosphere.


polymers (p.145)
A
a) Polythene is a hydrocarbon with strong C—C and C—H bonds.
These bonds are not readily attacked by chemicals.
b) An ethene molecule contains a carbon-carbon double bond whereas

an ethane molecule does not.
c) i) 'Saran' is more heat resistant. It has polar C—CI bonds. The polar
attractive forces between
'Saran' molecules are stronger than the attractive forces between
non-polar polythene molecules.
ii) Hydrogen chloride causes acid rain when discharged into the
atmosphere.


polymers (p.145)
Practice 28.2
1 The tablet container shown is made
from two different synthetic polymers.
a) These are two common types of polythene (PE).

i) Name the TWO common types of PE.
Low density polythene and high density polythene
ii) Suggest which type of PE is more suitable in making this container.
Explain your choice.
As the bottle is hard, high density polythene is more suitable.
b) State ONE property of polypropene which makes it suitable for making
caps of tablet containers. Any one of the following:
• Chemical resistant • Good barrier to moisture
• Non-toxic


polymers (p.145)
2 Polystyrene (PS) is a commonly used
synthetic polymer. The structure of PS
is shown.
a) Write the structural formula of the monomer of PS.

b) Suggest why PS does NOT have a constant relative molecular mass.
PS is a mixture of polymer molecules of different lengths.
c) SAN is a plastic material made from the copolymerisation of styrene with
acrylonitrile (CH2=CHCN). A part of the structure of SAN is shown below.
Acrylonitrile has polar –C≡N group.
The –C≡N groups hold the polymer
molecules of SAN by stronger polar
attractive forces.

Key terms (p.152)
plastic 塑膠 low density polythene 低密度聚乙烯

synthetic polymer 合成聚合物 high density polythene 高密度聚乙烯
polymer 聚合物 initiator 引發劑
monomer 單體 polypropene 聚丙烯
polymerisation 聚合作用 polyvinyl chloride 聚氯乙烯
addition 加成聚合作 polystyrene 聚苯乙烯
polymerisation 用
addition polymer 加成聚合物 low density polythene 低密度聚乙烯
repeating unit 重複單位 poly(methyl 2- 聚(2-甲基丙烯
methylpropenoate) 酸甲酯)

Summary (p.153)
1 A polymer is a compound consisting of very large molecules
formed by joining together many small molecules repeatedly.
2 Addition polymerisation is a reaction in which monomer
molecules join together repeatedly to form polymer molecules.
No atoms are lost from the monomer molecules during the
reaction.
3 Monomer molecules containing carbon-carbon double bonds
can undergo addition polymerisation to give addition polymers.
4 A repeating unit is the smallest part of a polymer molecule, and
the whole polymer molecule can be obtained by repeating it.

Summary (p.153)
5 The structures, properties and uses of some common
addition polymers are shown below:

Summary (p.153)

Summary (p.153)

Unit Exercise (p.155)
Note: Questions are rated according to ascending level of

difficulty (from 1 to 5):
question targeted at level 3 and above;

question targeted at level 5.
‘ * ’ indicates 1 mark is given for effective communication.


PART I KNOWLEDGE AND UNDERSTANDING
1 Complete the following concept map.

a) addition
b) addition
c) polythene
d) polypropene
e) polyvinyl
chloride
f) polystyrene
g) Perspex


PART II MULTIPLE CHOICE QUESTIONS
2 A polymer made from acrylic acid (CH2=CHCOOH) is shown below.
Which type of reaction results in the formation of this polymer?
A Addition
Answer: A
B Hydration
C Oxidation
D Substitution


3 1,1-difluoroethene can form a
polymer. Which of the following
can represent a part of the
structure of the polymer?
Answer: D
Explanation:


4 A section of the structure of an addition polymer is shown below:
What is the monomer of the polymer?

Answer: B
Explanation:


5 A portion of the structure of an addition polymer X is shown below:
Which of the following is the systematic name of the monomer of X based

on the given structure?
A 1,1-dichloro-2-methylethene
B 1,1-dichloropropene
C 1,2-dichloropropene Answer: B
D 3,3-dichloropropene
(HKDSE, Paper 1A, 2013, 14)

Unit Exercise (p.155) Answer: D
6 Polymer X has the structure shown below. Explanation: Option B—
Which of the following statements concerning X is INCORRECT?
A X is an addition polymer.
B The monomer of X is methylpropene.
C Van der Waals’ forces exist between the polymer chains of X.
D X belongs to the alkene homologous series.

7 Which of the following items can be made from low density

polythene?
A Bottle crates
B Margarine tubs
C Car bumpers Answer: D
D Wash bottles


8 Consider the carbon compound shown below.
Which of the following statements concerning this carbon compound is / are

correct?
(1) Its systematic name is 2-methylbutene.
(2) It can turn Br2 (in CH3CCl3) solution colourless quickly.
(3) It can form a polymer with structure shown below:
A (1) only Answer: B

B (2) only
Explanation:
C (1) and (3) only
(1) Its systematic name is 2-methylbut-1-ene
D (2) and (3) only
(3)


9 Which of the following compounds can undergo addition polymerisation?
Answer: A
Explanation:
A (1) and (2) only
(3) The C=C bonds in the benzene
B (1) and (3) only
ring of an aromatic compound do
C (2) and (3) only
NOT undergo addition
D (1), (2) and (3)
polymerisation.


10 Which of the following items can be made from polyvinyl chloride (PVC)?
(1) Drain pipes
(2) Table clothes
(3) Window frames
A (1) and (2) only

Answer: D
B (1) and (3) only
C (2) and (3) only
D (1), (2) and (3)


11 A polymer has the following structure:
Which of the following statements concerning the polymer are correct?

(1) It contains carboxyl groups.
(2) Its monomer can decolourise acidified KMnO4(aq).
(3) It can be used to make aircraft windows.
A (1) and (2) only Answer: C

B (1) and (3) only
C (2) and (3) only
D (1), (2) and (3)


12 Consider the two hydrocarbons shown.
Which of the following statements concerning the hydrocarbons is / are

correct?
(1) Both have the same molecular formula.
(2) X and Y react separately with cold acidified KMnO4(aq) to give the
same organic product.
(3) Both the polymerisation of X and that of Y give the same addition
polymer.
Answer: A
A (1) only
B (2) only
C (1) and (3) only
D (2) and (3) only


Explanation:
(2) X and Y react separately with cold
acidified KMnO4(aq) to give different
organic products.
(3) Polymerisation of X and that of Y

give different additional polymers.


13 Which of the following pairs of substances can be distinguished by using
acidified KMnO4(aq)?
(1) Pent-1-ene and pent-2-ene
(2) Cyclohexane and cyclohexene
(3) Polyethene and poly(chloroethene)
B (2) only
C (1) and (3) only
D (2) and (3) only


PART III STRUCTURED QUESTIONS
14 Synthetic polymers are very useful materials. Many objects previously
made of metals are now made of synthetic polymers. For each of the
following objects, suggest ONE advantage of using synthetic polymers
over using metals in making the object.
a) The casing for an electric rice cooker Electricity leakage can be
b) Gear wheel prevented. (1)
c) Storage tank for cold water
b) Any one of the following: c) Any one of the following:
• More corrosion resistant (1) • More corrosion resistant (1)
• Needs no lubricant (1) • Lighter / less dense (1)
• Strong but light in weight (1) • Can be moulded to different
• Can be moulded to different shapes more easily (1)
shapes more easily (1) • Good insulator / keep the
water cold (1)


15 The following diagrams show four items made of synthetic polymers.
For each of the items,

i) suggest ONE synthetic polymer which is suitable to make the item;
ii) give TWO properties of the suggested synthetic polymer which make it
suitable for making the item.


Item Synthetic polymer suitable for TWO properties of the synthetic
making the item polymer which make it suitable
a) bread bag polythene (1) • soft and flexible (1)
• waterproof (1)
b) raincoat polyvinyl chloride (1) Any two of the following:
• flexible (1)
• waterproof (1)
• easily coloured (1)
c) car light cover Perspex (1) Any two of the following:
• transparent (1)
• strong (1)
• rigid (1)
d) margarine tub polypropene (1) Any two of the following:
• chemical resistant (1)
• moisture resistant (1)
• non-toxic (1)
• does not flavour the food (1)


16 Large quantities of ethene are manufactured every year.
Ethene is produced by the following procedure:
a) Name Processes 1, 2 and 3.

Process 1: fractional distillation (1)
Process 2: cracking (1)
Process 3: fractional distillation (1)


b) Explain why ethene can form a polymer, but ethane CANNOT.
An ethene molecule contains a carbon-carbon double bond while an
ethane molecule does not. (1)
c) Explain the meaning of the term ‘addition polymerisation’.
Addition polymerisation is a reaction in which monomer molecules join together
repeatedly to form polymer molecules. (1)
No atoms are lost from the monomer molecules during the reaction. (1)
d) Write a chemical equation for
the addition polymerisation.
e) A steel storage tank for concentrated hydrochloric acid has an inner lining
of polythene. Explain the function of the lining of polythene in terms of the
chemistry concept involved.
Polythene lining is chemically inert / does not react with acid. (1)
It can prevent the acid from reacting with the steel storage tank.


17 Heavy fractions from petroleum can produce propene via cracking. Some
of the reactions of propene are shown below.
a) Consider Reaction 1.
i) Write the structural formula of the product.
ii) Give the systematic name of the product.

1,2-dibromopropane
iii) State the expected observation in the reaction.
The orange solution of bromine becomes
colourless quickly. (1)

b) Consider Reaction 2.
i) Suggest the reagent required.
Cold acidified dilute potassium permanganate solution (1)
ii) Name the type of reaction involved. Addition reaction (1)
iii) Give the systematic name of the product. Propane-1,2-diol (1)
iv) State the expected observation in the reaction.
The purple solution of potassium permanganate becomes colourless
quickly. (1)
c) Consider Reaction 3.
Describe how propene molecules react with each other to form polymer X.
Compounds with carbon-carbon double bonds can undergo addition
polymerisation. (1)
During addition polymerisation, part of the double bond of each propene
molecule is broken, and the molecule joins to neighbouring propene
molecules to make a molecule with a very long chain. (1)
No atoms are lost during the reaction.
High temperature / high pressure / catalyst is used. (1)


18 Tetradecane (C14H30) is a hydrocarbon found in the naphtha fraction of
petroleum. Tetradecane can be used as a starting material to produce a
wide variety of useful products. The scheme below shows how one such
product, polymer Y, can be produced from tetradecane.


a) Explain, from molecular level, why naphtha can be obtained from
petroleum by fractional distillation.
Components with different boiling points can be separated from each
other by fractional distillation. (1)
The longer the carbon chain in a hydrocarbon molecule, the higher the
boiling point of the hydrocarbon is. (1)
b) Name the homologous series to which both C2H4 and C4H8 belong.
Alkenes (1)
c) Identify compound X.
C8H18 (1)
d) Name polymer Y.
Polybut-2-ene (1)


19 The structure of polypropene is shown below.
a) The monomer of polypropene is propene. Suggest a chemical test to

show that propene is an unsaturated hydrocarbon.
a) Any one of the following:
• Add an orange solution of bromine dissolved in 1,1,1-trichloroethane to
propene. (1)
The orange solution of bromine becomes colourless quickly. (1)
• Add a purple solution of cold acidified dilute potassium permanganate
solution to propene. (1)
quickly. (1)


b) Explain, in terms of bonding, why objects made of polypropene are
resistant to chemical attacks.
Polypropene is a hydrocarbon with strong C-C and C-H bonds. These
bonds are not readily attacked by chemicals. (1)
c) Polypropene is used to make sandwich boxes. Suggest TWO properties,
other than resistant to chemical attacks, needed by polypropene to be
suitable for making a sandwich box.
Any two of the following:
• Waterproof (1)
• Non-toxic (1)
• Non-biodegradable (1)


20 Compound R has the following condensed structural formula:
(CH3)2CHCH2CH=CH2
a) Give the systematic name of R. 4-methylpent-1-ene (1)
b) Compound R undergoes addition polymerisation to form a polymer.
i) Explain the meaning of the term ‘addition polymerisation’.
Addition polymerisation is a reaction in which monomer molecules join
together repeatedly to form polymer molecules. (1)
ii) Write a chemical equation for the polymerisation.


21 Polystyrene (PS) is a commonly used synthetic polymer. The structure of
PS is represented as follows:
a) Write the structural formula of the monomer of PS.
b) Suggest why the relative molecular mass of PS is expressed using a

range of values instead of a single fixed value.
PS is a mixture of polymer molecules with different lengths. (1)


c) Expanded polystyrene has good heat insulating properties. Suggest why.
Air is a good insulator of heat. (1)
Trapping air in expanded polystyrene enhances the heat insulating properties.
d) Expanded polystyrene is commonly used as packing materials for delicate

articles.
State ONE property of expanded polystyrene associated with this usage.

It is light but still quite rigid. / It is an excellent shock absorbent. (1)


22 Ethene is obtained from the cracking of naphtha. Polyvinyl chloride (PVC)
can be obtained from ethene as shown below.
a) What is ‘cracking’?
Cracking is the breaking down of large hydrocarbon molecules with heat or
in the presence of a catalyst to produce smaller hydrocarbon molecules. (1)
b) What is the systematic name of CH2ClCH2Cl?
1,2-dichloroethane (1)
c) Name the type of polymerisation that produces PVC.
Addition polymerisation (1)


d) Draw the structure of PVC,
showing at least THREE repeating
units.
e) Products made of PVC may vary greatly in rigidity.

Give ONE rigid product made of PVC. Any one of the following:
• Bottles (1)
• Drain pipes (1)
• Window / door frames (1)
f) Both polythene (PE) and polyvinyl chloride (PVC) can be used to make
food wrap.
When incinerated, why would food wrap made from PVC cause more
serious pollution problem than food wrap made from PE?
Incineration of food wrap made from PVC will produce toxic gases / hydrogen
chloride / chlorine / dioxins while food wrap made from PE will not. (1)


23 Polymer B shown below can be used as water absorbing material in diapers. It can
be formed from the polymerisation of compound A.
a) Draw the structure of compound A and state its systematic name.

b) State the type of polymerisation for the formation of B from A.
c) Suggest why the relative molecular mass of B is expressed using a range of
values instead of a single fixed value.
(HKDSE, Paper 1B, 2016, 5(a)–(c))
Answers for the questions of the public examinations in Hong Kong
are not provided (if applicable).


24 Perspex can be used to make riot shields used by police. A section of the
structure of Perspex is shown below.
a) Write the structure formula of the monomer of Perspex.

b) Suggest TWO properties of Perspex which make it suitable for making
riot shields. Any two of the following: • Transparent (1) • Strong (1) • Rigid (1)
c) Perspex can be used instead of glass to make camera lenses.
State ONE advantage and ONE disadvantage of using Perspex instead
of glass to make camera lenses.
Advantage: It does not break easily. / It is lighter. (1)
Disadvantage: It can be quite easily scratched. (1)


25 Polythene (PE) and polyvinyl chloride (PVC) are two of the most commonly
used synthetic polymers.
a) Suggest reaction conditions for the formation of PE from its monomer.

Any one of the following:
• Peroxide; heat; high pressure (1)
• Catalyst; moderate pressure (1)
b) Write the structural formula of the monomer of PVC.
Give the systematic name of the monomer.
c) Explain why PVC is more rigid than PE.
PVC has polar C−Cl bonds. The polar attractive forces between PVC
molecules are stronger than the attractive forces between non-polar
PE molecules. (1)


26 Poly(propenenitrile) is an addition polymer. It can be made from propene.
a) Alkanes in petroleum can be used to manufacture propene. Two stages

are required.
Name the TWO stages.
Fractional distillation (1)
Cracking (1)


b) Look at the structural formula of propenenitrile:
i) Propenenitrile is an unsaturated compound.

How can you tell from the structural formula?
Propenenitrile has carbon-carbon double bond. (1)
ii) Draw the structure of poly(propenenitrile),
showing at least THREE repeating units.
iii) The polymerisation of propene gives polypropene.
The strength of poly(propenenitrile) is higher than that of polypropene.
Explain why.
Poly(propenenitrile) has polar −C N groups. The polar attractive forces
between the poly(propenenitrile) molecules are stronger than the
attractive forces between non-polar polypropene molecules. (1)


*27 Tetrafluoroethene undergoes polymerisation to form a polymer called
‘Teflon’. Using this example, describe this type of polymerisation.
(HKDSE, Paper 1B, 2018, 9)


Topic Exercise (p.164)
Note: Questions are rated according to ascending level of

difficulty (from 1 to 5):

question targeted at level 5.
‘ * ’ indicates 1 mark is given for effective communication.


PART I MULTIPLE CHOICE QUESTIONS
1 What is the systematic name of the following compound?
Answer: D Explanation:
A 1-bromo-2-ethylpropane
B 2-bromo-2-ethylpropane Thus, the systematic name of this
C 1-bromo-2-methylbutane compound is 2-bromo- 2-methylbutane.
D 2-bromo-2-methylbutane


2 What is the systematic name of the following compound?
CH3CH=CHCH(OH)CH3 Answer: D Explanation:
A 2-hydroxypent-3-ene
B 3-hydroxypent-1-ene
C pent-2-en-4-ol
D pent-3-en-2-ol


3 The diagram below shows an apparatus:
Answer: C
Which of the following mixtures can be separated by this apparatus?

A rock salt and sand
B propan-2-ol and water
C hexane (C6H14) and water
D methanoic acid and ethanoic acid


4 Which of the following would be formed when propene reacts with Br2 (in
CH3CCl3) solution? Answer: B
A 1,2-dibromopropene
B 1,2-dibromopropane
C A mixture of 1-bromopropene and 2-bromopropene
D A mixture of 1-bromopropane and 2-bromopropane
Explanation:


5 Monomer X undergoes addition polymerisation to give a polymer with
the repeating unit shown below.
What is monomer X? Answer: A

Explanation:
A but-2-enoic acid The structure of monomer
B but-3-enoic acid X is shown.
C 1-methylpropenoic acid
D 3-methylpropenoic acid
The acid contains 4 carbon atoms, and the

double bond between carbon atoms 2 and 3,
i.e. but-2-enoic acid.


6 Part of the structure of an addition polymer is shown below. It is made
using two different monomers.
What is monomer X?
A but-2-enoic acid Answer: B

B but-3-enoic acid Explanation:
C 1-methylpropenoic acid The polymer is made using ethene and but-1-
D 3-methylpropenoic acid ene.


7 Which of the following statements concerning petroleum is / are correct?
(1) It is a source of aliphatic hydrocarbons.
(2) It can be separated into liquids of different viscosity by a
separating funnel.
(3) It is a fossil fuel derived from ancient marine organisms.
A (1) only Answer: C

B (2) only
C (1) and (3) only
D (2) and (3) only


8 Which of the following statements concerning the measures to reduce air
pollutants is / are correct?
(1) Catalytic converters can be used to reduce carbon dioxide.
(2) Scrubbers can be used to reduce sulphur dioxide.
(3) Electrostatic precipitators can be used to reduce unburnt
hydrocarbons.
Answer: B
A (1) only Explanation:
B (2) only (1) Catalytic converters are used to reduce carbon
C (1) and (3) only monoxide, oxides of nitrogen and unburnt
D (2) and (3) only hydrocarbons.
(3) Electrostatic precipitators are used to reduce
particulates.


9 Which of the following processes increase global warming?
(1) Burning fossil fuel
(2) Decay of organic waste
(3) Farming cattle for beef
A (1) and (2) only

B (1) and (3) only Answer: D
C (2) and (3) only
D (1), (2) and (3)


10 Consider the following reaction of a
hydrocarbon:
Which of the following statements about the reaction is / are correct?

(1) Excess Br2(l) should be used.
(2) Light is needed.
(3) The reaction gives a single product. Answer: B
B (2) only (1) If excess Br2(l) is used, dibromo and tribromo
C (1) and (3) only compounds (i.e. and )
D (2) and (3) only
would be the major products.


11 Which of the following processes is / are exothermic?
(1) Combustion of methane
(2) Cracking of heavy oil
(3) Melting of wax Answer: A
B (2) only (2) and (3) Cracking of heavy oil and melting of wax
C (1) and (3) only take in heat. They are NOT exothermic processes.
D (2) and (3) only


12 The structures of organic compounds
A and B are shown below:
Which of the following statements concerning the two compounds is /

are correct?
(1) A and B belong to the same homologous series.
(2) A and B can be distinguished by acidified KMnO4(aq).
(3) Complete combustion of 1.0 g of A and complete combustion of
1.0 g of B would form the same mass of CO2(g).
B (2) only
C (1) and (3) only
D (2) and (3) only


Directions : Each question (Questions 13–16) consists
of two separate statements. Decide
whether each of the two statements is true
or false; if both are true, then decide
whether or not the second statement is a
correct explanation of the first statement.
Then select one option from A to D
according to the following table :
A Both statements are true and the 2nd statement is a
correct explanation of the 1st statement.
B Both statements are true but the 2nd statement is NOT
a correct explanation of the 1st statement.
C The 1st statement is false but the 2nd statement is true.
D Both statements are false.

1st statement 2nd statement
13 When using a Bunsen burner When using a Bunsen burner with

with the air hole fully open, the the air hole fully open, the fuelAnswer: C
burner gives a luminous flame. undergoes complete combustion.
Explanation: When using a Bunsen burner with the air hole fully open, the
burner gives a non-luminous flame.
14 In Hong Kong, natural gas is a Natural gas is a renewable Answer: D
common domestic fuel. energy source.
Explanation: Natural gas is NOT a common domestic fuel.
Natural gas is a non-renewable energy source.
15 Both pent-1-ene and pent-2- Both pent-1-ene and pent-2-ene

ene can decolourise a solution have the same molecular formula.
of bromine in 1,1,1- Answer: B
trichloroethane.


1st statement 2nd statement
16 Compared with hexane, Hexene has a higher carbon to

hexene gives more dark smoke hydrogen ratio than hexane. Answer: A
when burnt.


PART II STRUCTURED QUESTIONS
17 a) i) Coal is solid fossil fuel.
Name another fossil fuel. Petroleum / natural gas (1)
ii) Explain what is meant by the term ‘fossil fuel’.
Burn to release energy. (1)
Formed from the remains of dead organisms that lived millions of
years ago. (1)


b) The burning of fossil fuels is largely responsible for the formation of acid
rain. Two of the acids in acid rain are sulphuric acid and nitric acid.
i) Explain how the combustion of coal can form sulphuric acid.
Oxygen / air and sulphur (from coal) react to form sulphur dioxide. (1)
Sulphur dioxide reacts with oxygen / air to form sulphur trioxide. (1)
Sulphur trioxide reacts with water to form sulphuric acid. (1)
ii) High temperatures generated by the combustion of fossil fuels can lead
to the formation of nitric acid. Explain.
Oxygen and nitrogen react to form oxides of nitrogen. (1)
Oxides of nitrogen react with water, making nitric acid. (1)
(Cambridge IGCSE, 0620/33, Paper 3, Jun. 2015, 4(a),(b)(i)–(ii))


18 Some regions tend to generate electricity more by natural gas but less by
coal. Give TWO reasons from environmental protection consideration.
(HKDSE, Paper 1B, 2015, 8(c))



19 Three common pollutants in the air are carbon monoxide, the oxides of
nitrogen, NO and NO2, and unburnt hydrocarbons. They are all emitted by
motor vehicles.
a) Describe how the oxides of nitrogen are formed.
Nitrogen and oxygen react at high temperatures in the engine. (1)
b) Describe how a catalytic converter reduces the emission of these three
pollutants.
Carbon monoxide reacts with nitrogen monoxide as they pass
through the catalyst in the catalytic converter. Less harmful carbon
dioxide and nitrogen are formed. (1)
The excess carbon monoxide and unburnt hydrocarbons are oxidised
by air to carbon dioxide and water. (1)
(Cambridge IGCSE, 0620/31, Paper 3, Nov. 2014, 5(a)–(b))


20 Both pentane (C5H12) and octane (C8H18) are members of the same
homologous series.
a) Which compound, pentane or octane, will burn with a more sooty
flame? Explain your answer.
Octane will burn with a more sooty flame.
The octane molecule has a higher carbon to hydrogen ratio than the
pentane molecule. (1)
b) Write the structural formulae of TWO other alkanes which have the
same molecular formula as pentane.


c) The skeletal formula of compound A is shown.
It has the same molecular formula as octane.
i) Give the systematic name of compound A. 2,2,3-trimethylpentane
ii) Which compound, octane or A, has a higher boiling point? Explain
your answer.
Octane has a higher boiling point.
The octane molecule is longer and somewhat spreadout. The
molecule has a larger surface area, allowing a greater area of contact
with neighbouring molecules. (1)
In contrast, the molecule of A is more compact, adopting a roughly

spherical shape. The molecule has a smaller surface area for coming
into contact with neighbouring molecules. (1)
Thus, the van der Waals’ forces among octane molecules are
stronger than those among molecules of A. (1)


21 An oil company refines crude oil into different fractions. This table shows
the volume of each fraction made from a barrel of crude oil in litres. It also
shows the range of the number of carbon atoms in the molecules in each fraction.
Describe the trend in boiling points of the fractions from the top to the
bottom of the barrel.
Explain, using data from the table, why the boiling points change from one
fraction to the next.
(OCR GCSE (Higher Tier), Chemistry A (21st Century Science), A172/02, Jun. 2014,
4)


The boiling points of the fractions increase from the top to the bottom. (1)
The sizes of molecules in the fractions increase from the top to the bottom.
(1)
Thus, the strength of van der Waals’ forces among molecules increases
from the top to the bottom. (1)
Communication mark (1)


22 ‘Lava lamps’ have become popular in recent years. These lamps contain
two immiscible liquids of slightly different densities. When switched on,
the heat of the bulb causes one of the liquids to rise up and then cool
down at the top and fall in a bubble through the other liquid.
A substance that is used in lava lamps is the liquid ‘ethylene glycol’.

Ethylene glycol contains carbon, hydrogen and oxygen only. Its relative
molecular mass is 62.0. Complete combustion of 1.24 g of ethylene glycol
gives 1.76 g of carbon dioxide and 1.08 g of water.
a) Deduce the molecular formula of ethylene glycol.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0)
b) Given that ethylene glycol has two functional groups, draw a possible
structure of ethylene glycol.




23 Chloromethanes, such as dichloromethane and trichloromethane, are
produced in industry as they have many uses.
Trichloromethane (CHCl3) has been used in the manufacture of the

refrigerant chlorodifluoromethane.
Chlorine can react with dichloromethane (CH2Cl2) to form

trichloromethane.
The reaction may be represented by a mechanism involving three stages

— initiation, propagation and termination.
a) Show the initiation step of the reaction between chlorine and

dichloromethane.
Cl–Cl à Cl• + •Cl (1)


b) Give the TWO propagation steps
of the reaction between chlorine
and dichloromethane to form
trichloromethane.
c) Show the termination step which leads to the formation of

tetrachloroethane.
d) Give ONE essential condition for this reaction and name the type of
reaction involved.
Ultraviolet light / heat / radical initiator (1)
Substitution reaction (1)


24 Organic wastes can be used as an alternative energy source. Under
suitable conditions, the wastes can be digested by bacteria to give a
gaseous mixture containing a high proportion of methane. Methane can
be used as a fuel.
a) Suggest ONE organic waste that can be used for this purpose.
Food waste / animal waste (1)
b) Write the chemical equation for the complete combustion of methane.
CH4(g) + 2O2(g) à CO2(g) + 2H2O(l) (1)
c) Methane is one of the greenhouse gases.
Describe how greenhouse gases help to maintain temperatures on the
Earth.
The Earth absorbs the radiation from the sun and also emits
infrared radiation back into space when it cools down. (1)
Greenhouse gases absorb some of the infrared radiation emitted
from the Earth and re-emit them in all directions. This keeps the
atmosphere warm for life to sustain on Earth. (1)


25 Alkenes can be made from alkanes by cracking.
a) Explain the term ‘cracking’.
Cracking is the breaking down of large hydrocarbon molecules with heat or
in the presence of a catalyst to produce smaller hydrocarbon molecules. (1)
b) Suggest TWO importance of cracking in industry.
• To produce alkenes which can make a huge range of other compounds. (1)
• To convert heavy oil to petrol. (1)
c) The cracking of alkane X was studied in a school laboratory using the
set-up shown below.


During the experiment, one molecule of alkane X produced one molecule of
hexane (C6H14) and two molecules of ethene.
i) What is the molecular formula of alkane X? C10H22 (1)
ii) Complete the diagram to show how the gaseous product could be collected.
iii) The gaseous product (ethene) was shaken thoroughly with a few drops of
cold acidified dilute KMnO4(aq).
(I) State the expected observation.
The purple solution of potassium permanganate becomes colourless quickly. (1)
(II) Write the structural formula of the product formed in the reaction. Give
its systematic name.


26 Oxygenates are often blended in petrol to reduce carbon monoxide and
soot that are produced during the combustion of petrol.
MTBE, an oxygenate, is manufactured according to the equation below.
a) Give the systematic names of compounds X and Y.

Compound X: methylpropene (1)
Compound Y: methanol (1)
b) Name the homologous series of which compound Y is a member.
Alkanols (1)
c) Name the type of formula used to represent compound X
and MTBE. Skeletal formula (1)


d) Compound X can be obtained by cracking a larger hydrocarbon C15H32.
i) Write the chemical equation for the cracking of C15H32 to produce
compound X and one other product.
C15H32 à C4H8 + C11H24 (1)
ii) A catalyst is one condition needed to crack a hydrocarbon.
State ONE other condition needed to crack a hydrocarbon.
Heat / high temperature (1)


27 Ethene, propene and but-1-ene are members of the alkene homologous
series.
a) Describe THREE features of a member of a homologous series.
Any three of the following:
Members
• have the same general formula. (1)
• differ from the next by a −CH2− unit. (1)
• have similar chemical properties. (1)
• have physical properties showing a trend. (1)
b) State and explain which of the compounds has the highest boiling point.
But-1-ene has the highest boiling point.
The molecular size is the greatest for but-1-ene. (1)
Thus, the strength of van der Waals’ forces among but-1-ene molecules
is the greatest. (1)


c) Write the structural formula and systematic name of an alkene
containing five carbon atoms per molecule. Any one of the following:


d) Describe a chemical test to distinguish between an alkane and an
alkene, giving the expected observation in each case.

alkane and alkene separately. (1)
The orange solution of bromine becomes colourless quickly when
added to alkene.
(1)
The orange solution of bromine becomes colourless slowly when
added to alkane in the presence of ultraviolet light / heat.

solution to alkane and alkene separately. (1)
quickly when added to alkene. (1)
Alkane gives no observable change.


28 a) Cracking of alkanes gives alkenes.
Write a chemical equation for the cracking of C21H44 in which ethene
and propene are produced in a 3:2 mole ratio together with one other
product. C21H44 à 3C2H4 + 2C3H6 + C9H20 (1)
b) Propene undergoes addition polymerisation to form polypropene.
i) Explain the meaning of the term ‘addition polymerisation’.
Addition polymerisation is a reaction in which monomer molecules join
together repeatedly to form polymer molecules. (1)


ii) Explain why propene can form a polymer, but propane CANNOT
C21H44 à 3C2H4 + 2C3H6 + C9H20 (1)
iii) Write the chemical equation for the formation of polypropene from
propene.
iv) Explain why polypropene is a solid at room conditions.

Polypropene has long-chain molecules. (1)
The van der Waals’ forces among the molecules are strong. (1)


29 Ethene and ethane are hydrocarbons.
a) Suggest how ethene can be converted to ethane.
b) Suggest a chemical test to distinguish between ethane and ethene.
(HKDSE, Paper 1B, 2018, 4(c))



30 The structure of Perspex is shown below.
a) Draw the structure of the monomer of Perspex.

b) Perspex can be used to make aircraft windows.
One of the properties that make Perspex suitable for making aircraft
windows is its transparency. Suggest TWO other properties of Perspex
which make it suitable for this use.
Any two of the following:
• Does not break when hit (1) • Does not corrode / does not react with moist
air (1)
• Not degraded by sunlight (1) • Lightweight (1)
• Durable (1) • High melting point (1)
• Strong (1) • Rigid (1)


31 Allyl chloride, CH2=CHCH2Cl, is used in the production of polymers.
a) Allyl chloride is a member of a homologous series.
i) What is meant by the term ‘homologous series’?
A 'family' of compounds that have a common functional group,
with each successive member differing by a −CH2− unit, is
called a homologous series. (1)
ii) What is the general formula of the homologous series of which allyl
chloride is a member?
CnH2n-1Cl (1)
iii) Write the skeletal formula of allyl chloride.


b) i) State the type of polymerisation for the formation of polymer from allyl
chloride. Addition polymerisation (1)
ii) Draw the structure of the polymer, showing at least THREE repeating
units.


32 The cyclic carbon compounds shown below are members of the same
homologous series and have the same general formula.
a) What is the functional group in these compounds?

Carbon-carbon double bond (1)
b) Why are these compounds described as hydrocarbons?
They contain only hydrogen atoms and carbon atoms. (1)
c) State the general formula for members of this series. CnH2n+2 (1)
d) Cyclopentene can be polymerised to give polycyclopentene.
Draw a section of polycyclopentene to show THREE repeating units.


e) Both cyclohexene and cyclohexane contain six carbon atoms per molecule.
Suggest a chemical test to distinguish cyclohexene from cyclohexane. State
your expected observations.
cyclohexene and cyclohexane separately. (1)
The orange solution of bromine becomes colourless quickly when added to
cyclohexene.
The orange solution of bromine becomes colourless slowly when added to (1)
cyclohexane in the presence of ultraviolet
light / heat.
solution to cyclohexene and cyclohexane separately. (1)
quickly when added to cyclohexene. (1)
Cyclohexane gives no observable change.


33 Both polythene (PE) and ‘Saran’ can be used to make food wrap, but
‘Saran’ is more suitable than PE in making food wrap for use in
microwave ovens.
a) The monomer of PE is ethene. Suggest a chemical test to show that
ethene is an unsaturated compound.
b) ‘Saran’ can be formed from the polymerisation of the compound
shown below:
i) State the systematic name of this compound.

ii) Name the type of polymerisation involved in forming ‘Saran’.
iii) Draw the structure of ‘Saran’, showing at least THREE repeating
units.


c) In terms of intermolecular force, explain why ‘Saran’ is more suitable
than PE in making food wrap for use in microwave ovens.
d) When incinerated, why would food wrap made from ‘Saran’ cause
more serious pollution problem than food wrap made from PE?
(HKDSE, Paper 1B, 2014, 3)

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Topic 7 Fossil Fuels and Carbon Compounds

Unit 28 Addition polymers

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28.2 Why are synthetic polymers so useful?

Continued on next page

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28.1 Synthetic polymers all around you (p.136)

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28.2 Why are synthetic polymers so useful?

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28.3 Addition polymerisation of ethene (p.139)

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28.3 Addition polymerisation of ethene (p.139)

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28.3 Addition polymerisation of ethene (p.139)

w The section inside the bracket is the repeating unit (重複單位):

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28.3 Addition polymerisation of ethene (p.139)

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28.3 Addition polymerisation of ethene (p.139)

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28.4 Making other synthetic polymers (p.142)

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28.4 Making other synthetic polymers (p.142)

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28.4 Making other synthetic polymers (p.142)

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28.4 Making other synthetic polymers (p.142)

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28.4 Making other synthetic polymers (p.142)

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28.4 Making other synthetic polymers (p.142)

a) Draw the repeating unit of the polymer.

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28.4 Making other synthetic polymers (p.142)

a) State the systematic name of compound A. Propenoic acid

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28.5 Uses of some common addition

Structure of LDPE Structure of HDPE

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28.5 Uses of some common addition

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28.5 Uses of some common addition

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28.5 Uses of some common addition

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28.5 Uses of some common addition

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28.5 Uses of some common addition

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28.5 Uses of some common addition

Preparing polystyrene Investigating the properties of

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28.5 Uses of some common addition

i) In terms of intermolecular forces, explain why 'Saran' is more suitable

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28.5 Uses of some common addition

b) An ethene molecule contains a carbon-carbon double bond whereas