CHEMISTRY

QUESTIONSHEETS

AS TOPIC 15

APPLIED ORGANIC CHEMISTRY I

AS Level

Questionsheet

DISTILLATION OF PETROLEUM

17 marks

Questionsheet

CRACKING

17 marks

Questionsheet

FUELS

16 marks

Questionsheet

EPOXYETHANE AND ETHANE-1,2-DIOL

16 marks

Questionsheet

ADDITION POLYMERS

19 marks

Questionsheet

POLY(CHLOROETHENE)

15 marks

Questionsheet

HALOALKANES AS SYNTHETIC INTERMEDIATES

22 marks

Questionsheet

CFCs

16 marks

Questionsheet

USES OF OTHER ORGANIC HALOGENOCOMPOUNDS

14 marks

Questionsheet

10

FERMENTATION

14 marks

Questionsheet

11

SYNTHETIC ETHANOL PROCESS

16 marks

Questionsheet

12

ETHANOL AS A FUEL

16 marks

Questionsheet

13

DISPOSAL OF ORGANIC WASTE

17 marks

Authors
Trevor Birt
Donald E Caddy
Andrew Jones
Editor
John Brockington

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Andy Shepherd

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TOPIC 15 Questionsheet 1

AS Level

DISTILLATION OF PETROLEUM
a) (i)

Give a brief description of the chemical composition of petroleum (crude oil).

....................................................................................................................................................................... [1]
(ii) Petroleum from the Middle East is described as heavy crude oil, in contrast to that from the North Sea,
which is light crude. What do these descriptions mean in terms of composition?
....................................................................................................................................................................... [1]
b) The first major treatment that petroleum receives at an oil refinery is fractional distillation, to separate it into
fractions.
(i)

What is a fraction?

....................................................................................................................................................................... [2]
(ii) On what physical property of compounds is the separation based?
....................................................................................................................................................................... [1]
c) In the space below, sketch a plant used in the primary distillation of petroleum.

[3]
d) Label your diagram in c) to show clearly:
(i)

the temperature gradient,

(ii) where at least four major fractions are drawn off.

[1]
[4]

e) Name the material drawn off from the bottom of the plant, and give one of its major uses.
Material ......................................................................................................................................................... [1]
Use ................................................................................................................................................................. [1]
f) What is the major difference between the operation of fractional distillation in industry and in the laboratory?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
TOTAL / 17

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TOPIC 15 Questionsheet 2

CRACKING
a) Textbooks say that most naphtha (heavy gasoline) is cracked to give more useful substances.
(i) Why cannot naphtha be used as a fuel in motor cars?
....................................................................................................................................................................... [1]
(ii) A typical constituent of naphtha is decane, C10H22. Write two chemical equations to show likely ways in
which decane will undergo cracking.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(iii) Give three ways in which the products of cracking are more useful.
1. ................................................................................................................................................................
2. ................................................................................................................................................................
3. ............................................................................................................................................................ [3]
b) Both thermal cracking and catalytic cracking are employed in the oil industry. Compare these two processes
by completing the following table.
Thermal cracking

Catalytic cracking

Conditions

Type of bond breaking

Type of reaction intermediate

Principal products

[9]
c) Explain why, in catalytic cracking, catalysts are considered as variable costs rather than fixed costs, even
though catalysts are not consumed in catalysed reactions.
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
TOTAL / 17

AS Level

TOPIC 15 Questionsheet 3

FUELS
a) Methane and octane have standard enthalpies of combustion of 882.0 kJ mol-1 and -5512 kJ mol-1
respectively.
(i)

For each of these compounds, calculate the enthalpy change per gram of fuel combusted.
Methane ................................................................................................................................................. [1]
Octane ................................................................................................................................................... [1]

(ii) In the light of your answer to (a) (i), give two reasons why motor cars are more likely to be fuelled by
octane than by methane.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
b) (i) What is pre-ignition in the internal combustion engine and what problems does it cause?
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) How is the octane number (RON) of a fuel defined?
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
c) (i)

The octane number of a fuel can be raised by adding benzene or tetraethyllead. State one disadvantage
of each.
Benzene ............................................................................................................................................... [1]
Tetraethyllead ..................................................................................................................................... [1]

(ii) Give, with an example, one other method of improving octane number that does not incur either of these
disadvantages.
Method .................................................................................................................................................. [1]
Example ................................................................................................................................................. [1]
d) (i)

In what essential respect does a diesel engine differ from a petrol engine?

....................................................................................................................................................................... [1]
(ii) In what essential respect does diesel fuel differ from petrol?
....................................................................................................................................................................... [1]
(iii) What pollutant, believed to be a serious health hazard, is present to a much greater extent in diesel
exhaust fumes than in petrol exhaust fumes?
....................................................................................................................................................................... [1]
TOTAL / 16

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AS Level

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TOPIC 15 Questionsheet 4

EPOXYETHANE AND ETHANE-1,2-DIOL

Epoxyethane and ethane-1,2-diol are two important compounds manufactured from ethene.
a) (i)

Write a balanced equation, with state symbols, for the conversion of ethene to epoxyethane by reaction
with a large excess of oxygen at high pressure.

....................................................................................................................................................................... [1]
(ii) What catalyst is used for this process?
....................................................................................................................................................................... [1]
(iii) Why does a high pressure give a better yield of epoxyethane?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(iv) Although all high pressure processes carry the risk of an explosion, the hazard is particularly severe in
this process. Why?
....................................................................................................................................................................... [1]
b) Epoxyethane can be hydrated to give ethane-1,2-diol, and reacted with alcohols to give products which can
be used as solvents and plasticisers.
(i)

Despite the fact that epoxyethane is an ether, and ethers are generally inert, epoxyethane is a very
reactive compound. How do you account for this?

...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) Write a chemical equation for one molecule of epoxyethane reacting with one molecule of methanol.

[1]
(iii) Write an equation for the product of b)(ii) reacting with a further molecule of epoxyethane to give a
secondary product.

[1]

TOTAL(Continued...)
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TOPIC 15 Questionsheet 4 Continued

EPOXYETHANE AND ETHANE-1,2-DIOL

c) Ethane-1,2-diol (glycol) is used as an antifreeze in car radiators. Although monohydric alcohols can also be
used for the purpose, ethane-1,2-diol is particularly suitable. Why is this?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
d) Ethane-1,2-diol is also used for the production of the polyester Terylene, by condensation polymerisation
with benzene-1,4-dicarboxylic acid (terephthalic acid).
(i) What is meant by the term condensation in this context?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) Write down the structural formula of benzene-1,4-dicarboxylic acid.

[1]
(iii) Explain why a polyester is formed, rather than a simple ester.
...........................................................................................................................................................................
....................................................................................................................................................................... [1]
e) State one other major use of ethane-1,2-diol.
....................................................................................................................................................................... [1]

TOTAL / 16

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TOPIC 15 Questionsheet 5

ADDITION POLYMERS
a) Define the terms monomer, addition polymer and high polymer.
Monomer ....................................................................................................................................................... [1]
Addition polymer ........................................................................................................................................... [1]
High polymer .....................................................................................................................................................
....................................................................................................................................................................... [2]
b) (i)

What is the structural difference between low density poly(ethene) (LDPE) and high density
poly(ethene) (HDPE)?

...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) Under what reaction conditions is LDPE obtained?
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
(iii) The production of HDPE requires the use of a Ziegler catalyst. Give an example of one such catalyst.
....................................................................................................................................................................... [1]
(iv) Give two advantages of HDPE over LDPE.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]

TOTAL(Continued...)
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TOPIC 15 Questionsheet 5 Continued

ADDITION POLYMERS
c) (i)

Write a balanced chemical equation for the polymerisation of propene.

[2]
(ii) Give one use of poly(propene) and state why this polymer is used for the purpose rather than poly(ethene).
Use......................................................................................................................................................... [1]
Advantage .............................................................................................................................................. [1]
d) (i) Perspex is an addition polymer with the following structural formula:
CH3
CH2

C
COOCH3

Write down the structure of the monomer.

[1]
(ii) Natural rubber is made by the polymerisation of 2-methylbut-2-ene. Write down the structure of natural
rubber, showing clearly one repeat unit in the polymer chain.

[2]

TOTAL / 19

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TOPIC 15 Questionsheet 6

POLY(CHLOROETHENE)
a) Write a chemical equation, using structural formulae, for the polymerisation of chloroethene.

[1]
b) What is the common commercial name for poly(chloroethene)?
....................................................................................................................................................................... [1]
c) How can you account for the fact that poly(chloroethene) is much stiffer than poly(ethene)?
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
d) (i)

How can unplasticised poly(chloroethene) (UPVC) be converted into plasticised poly(chloroethene)?

....................................................................................................................................................................... [1]
(ii) What is the outstanding physical difference between the two materials?
....................................................................................................................................................................... [1]
(iii) Unplasticised poly(chloroethene) is used for making window frames. What outstanding property makes
it more suitable than poly(phenylethene) (polystyrene) for this purpose?
....................................................................................................................................................................... [1]
(iv) Plasticised poly(chloroethene) is widely used for the interior trim of vehicles. What outstanding property
makes it more suitable than poly(ethene) for this purpose?
....................................................................................................................................................................... [1]
e) Would you use poly(ethene) or poly(chloroethene) to make a container for concentrated aqueous sodium
hydroxide? Explain your choice.
...........................................................................................................................................................................
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [4]
f) State two problems which are associated with the disposal of waste polychloro(ethene).
1. ........................................................................................................................................................................
2. .................................................................................................................................................................... [2]

TOTAL / 15

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TOPIC 15 Questionsheet 7

AS Level

HALOALKANES AS SYNTHETIC INTERMEDIATES

Haloalkanes are versatile intermediates in organic synthesis. The following flow diagram shows in outline how
bromoethane (compound A) can be converted to compounds B, C, D, E, F and G.

C2H6SO4

Reagent(s)

Reagent(s)

Conditions

Conditions

Reagent(s)
B

C2H4

C2H6O

C2H4O2

C3H6O2

Conditions

Reagent(s)

Reagent(s)

Conditions

Conditions

Reagent(s)
A C2H5Br

Conditions

Reagent(s)
Conditions

Reagent(s)
F C3H5N

Conditions

a) Give the names of compounds B, C, D, E, F and G.

B = .............................................................................

C = ............................................................................

D = .............................................................................

E = ............................................................................

F = .............................................................................

G = ........................................................................ [6]

b) Complete the diagram by inserting reagents and conditions for the conversions shown.

[16]
TOTAL / 22

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TOPIC 15 Questionsheet 8

AS Level

CFCs
A major environmental problem associated with the large scale use of halogenoalkanes is their effect on the
ozone layer in the upper atmosphere. CFCs are of particular concern.
a) (i)

What do the letters CFC stand for?

....................................................................................................................................................................... [1]
(ii) Write down the structural formula of 1,1-dichloro-2,2-difluoroethane, commonly referred to as
CFC 12.

[1]
(iii) In the past CFCs have been widely used as aerosol propellants, but their use for this purpose has been
largely abandoned. Give two other applications.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
b) Trioxygen (commonly called ozone) in the upper atmosphere decomposes into dioxygen by reaction with
atomic oxygen, as shown by Equation 1.
O3 + O 2O2

Equation 1

In the absence of a catalyst the reaction is slow, but in the presence of CFCs a somewhat faster free radical
chain reaction can occur.
(i)

What is a free radical?

....................................................................................................................................................................... [1]
(ii) The chain reaction is initiated by the homolytic fission (by UV light) of a CCl bond. Explain why
chlorine free radicals are produced, rather than fluorine free radicals.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(iii) The initiation stage is followed by a propagation stage involving two reactions. Each of these uses up a
free radical and produces another sort of free radical. Each of them also consumes a molecule of reactant
(see Equation 1) and gives a molecule of the final product. Write equations for these two propagation
reactions.
Reaction 1 ............................................................................................................................................. [1]
Reaction 2 ............................................................................................................................................. [1]

TOTAL(Continued...)
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AS Level

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TOPIC 15 Questionsheet 8 Continued

CFCs
(iv) Explain why one chlorine free radical could react with literally thousands of ozone molecules.
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(v) Why is the rate of decomposition of ozone still low, even in the presence of CFCs?
....................................................................................................................................................................... [1]
c) (i)

Briefly explain the serious health hazard posed by depletion of the ozone layer.

...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) What other environmental problem do CFCs present, even at low concentrations?
....................................................................................................................................................................... [1]
(iii) Suggest one substance which could be used as a replacement for CFCs in most applications.
....................................................................................................................................................................... [1]

TOTAL / 16

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TOPIC 15 Questionsheet 9

AS Level

USES OF OTHER ORGANIC HALOGENOCOMPOUNDS

a) Chlorinated hydrocarbons, such as tetrachloromethane and tetrachloroethene, are widely used in industry
and commerce as degreasing solvents. Tetrachloromethane (carbon tetrachloride) is used in the engineering
industry to degrease metal components before they are painted or electroplated.
(i)

Why is the degreasing of components so important?

....................................................................................................................................................................... [1]
(ii) State what precaution must be taken when using tetrachloromethane, and give the reason for this.
Precaution ............................................................................................................................................. [1]
Reason ................................................................................................................................................... [1]
(iii) What is the commercial (i.e. high street) application of tetrachloroethene (perchloroethylene)?
....................................................................................................................................................................... [1]
b) (i)

Unplasticised polyvinyl chloride (UPVC), otherwise known as poly(chloroethene), is used for

manufacturing doors and window frames. State three advantages of UPVC for this purpose over traditional
building materials, such as wood.

...........................................................................................................................................................................
....................................................................................................................................................................... [3]
(ii) Name another halogen-containing plastic and state its use.
Name ..................................................................................................................................................... [1]
Use......................................................................................................................................................... [1]
c) The adoption of organic chlorocompounds as herbicides and pesticides has been due in part to the strength of
the C Cl covalent bond.
(i)

What advantage does this offer?

....................................................................................................................................................................... [1]
(ii) What is the associated disadvantage?
....................................................................................................................................................................... [1]
d) Bromochlorodifluoromethane (BCF) is commonly used in fire extinguishers.
(i)

Explain how this compound works in putting out fires.

...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) Why is it much safer, when fighting electrical fires, to use BCF rather than a foam extinguisher?
....................................................................................................................................................................... [1]
TOTAL / 14

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TOPIC 15 Questionsheet 10

AS Level

FERMENTATION
Although ethanol for industrial purposes is manufactured in the UK by the hydration of ethene, the anaerobic
fermentation of sugar solutions is used for the production of alcoholic beverages. Fermentation is carried out in
the presence of yeast, which acts as the source of an enzyme called zymase.
a) (i)

Name a simple sugar which could be fermented to produce ethanol.

....................................................................................................................................................................... [1]
(ii) What is meant by the term anaerobic?
....................................................................................................................................................................... [1]
(iii) Write a balanced equation for the fermentation of a simple sugar.
....................................................................................................................................................................... [2]
(iv) What is the role of zymase in the fermentation?
....................................................................................................................................................................... [1]
b) (i)

Draw a labelled diagram of a simple apparatus which could be used to investigate how the rate of
fermentation varies with temperature.

[2]
(ii) On the axes below, sketch the shape of the graph you would expect to obtain from the results of the
experiment in b)(i).
Rate

Temperature

[1]

(iii) Comment on the shape of your graph in b)(ii).

...........................................................................................................................................................................
....................................................................................................................................................................... [2]

(Continued...)
TOTAL
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AS Level

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TOPIC 15 Questionsheet 10 Continued

FERMENTATION
c) In Brazil, ethanol is made by fermentation and added to petrol on a large scale. The product is called gasohol.
Explain why this is particularly beneficial to countries like Brazil, and identify the main economic and
environmental benefits of this practice.
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
d) State two advantages (other than economic) of manufacturing industrial ethanol in the UK by the hydration
of ethene rather than fermentation.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]

TOTAL / 14

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TOPIC 15 Questionsheet 11

AS Level

SYNTHETIC ETHANOL PROCESS

Industrial ethanol is manufactured in the UK by the hydration of ethene, a reversible gaseous phase reaction in
which ethene and steam are compressed to a pressure of 70 atm and then passed over a catalyst, of phosphoric(V)
acid absorbed on silica, maintained at a temperature of 300 C.
a) (i)

Write an equation for the hydration of ethene.

....................................................................................................................................................................... [1]
(ii) What mechanistic type is the reaction?
....................................................................................................................................................................... [1]
b) The reaction is believed to occur via an intermediate X, shown below. This reacts with a molecule of water
to give protonated ethanol, Y, from which ethanol is formed by the loss of a proton.
+

CH3

CH2

:OH2
CH3

CH2
O

(i)

CH2

CH3
+

CH3

CH2
+

O
H

OH2

What type of reaction intermediate is X?

....................................................................................................................................................................... [1]
(ii) One of the curly arrows in the above mechanism has been incorrectly printed. Draw a circle round it,
and state what is wrong with it.
....................................................................................................................................................................... [1]
c) Given that the hydration of ethene is exothermic, state one advantage and one disadvantage of conducting the
process at a high temperature.
Advantage ...................................................................................................................................................... [1]
Disadvantage ................................................................................................................................................. [1]

TOTAL(Continued...)
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TOPIC 15 Questionsheet 11 Continued

SYNTHETIC ETHANOL PROCESS

d) (i)

State and explain the main reason for operating the process at a high pressure.

...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
(ii) Give two economic disadvantages of high pressure processes.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
e) (i)

Why is the catalyst absorbed on to silica?

....................................................................................................................................................................... [1]
(ii) What effect (if any) does the catalyst have on the yield of ethanol at equilibrium?
....................................................................................................................................................................... [1]
f) List the three essential stages that you would expect to be involved in turning the mixture of hot gases from
the converter into industrial methylated spirits.
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]

TOTAL / 16

AS Level

TOPIC 15 Questionsheet 12

ETHANOL AS A FUEL
The use of ethanol as a fuel is being promoted on the grounds that, since it can be made by the fermentation of
plant products, it is a renewable energy source. However, before petrol could be replaced by ethanol, its effect on
the environment would have to be assessed.
a) Write equations for the complete combustion of 1 mole of (i) octane, and (ii) ethanol.
(i)

Octane ................................................................................................................................................... [1]

(ii) Ethanol .................................................................................................................................................. [1]

b) Calculate the enthalpy change for the complete combustion of 1 dm3 of (i) octane, and (ii) ethanol.
(i)

Octane (Density of octane = 0.72 g cm-3. Hc (C8H18(l)) = -5512 kJ mol-1)

...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) Ethanol (Density of ethanol = 0.79 g cm-3. Hc (C2H5OH(l)) = -1371 kJ mol-1)
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
c) Calculate the mass of carbon dioxide produced by the complete combustion of (i) 1 dm3 of octane, and (ii)
1dm3 of ethanol.
(i)

1 dm3 of octane

...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) 1 dm3 of ethanol
....................................................................................................................................................................... [2]
d) Hence calculate the mass of carbon dioxide produced per kilojoule of energy for (i) octane, and (ii) ethanol.
Comment on your results with regard to impact on the environment.
(i)

Octane ................................................................................................................................................... [1]

(ii) Ethanol .................................................................................................................................................. [1]

Comment ............................................................................................................................................................
....................................................................................................................................................................... [1]
e) Why should ethanol made by fermentation be regarded as a greener fuel (i.e. one which is more friendly to
the environment) than synthetic ethanol?
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
TOTAL / 16

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AS Level

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TOPIC 15 Questionsheet 13

DISPOSAL OF ORGANIC WASTE

Household waste and much industrial waste is largely organic. Some can be recycled; otherwise it is generally
tipped in landfill sites or incinerated.
a) (i) Some plastics are recycled by melting them, but the process is difficult to operate economically. Why is
this?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) How can two other types of organic waste material be recycled?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
b) State two disadvantages of disposing of waste in landfill sites.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
c) Incineration avoids the disadvantages of landfill sites and has the additional advantage that the process is
exothermic. Give two ways in which the heat released could be put to good use.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
d) To avoid atmospheric pollution, incineration must be carried out at a sufficiently high temperature and with
a plentiful supply of air. Explain the pollution problems stemming from (i) too low a temperature, and (ii)
insufficient oxygen.
(i)

Too low a temperature

....................................................................................................................................................................... [2]
(ii) Insufficient oxygen
....................................................................................................................................................................... [2]
e) State and explain the environmental problem that can arise from the incineration of sulphur- and nitrogencontaining materials.
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
f) Suggest how the fumes from an incinerator could be treated chemically so as to reduce noxious emissions.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
TOTAL / 17