OXFORD AQA INTERNATIONAL AS-LEVEL

CHEMISTRY (9620)

ORGANIC
CHEMISTRY
Alkanes

Worksheet

Name: ________________________

Class: ________________________

Date: ________________________
Q1.
This question is about alkanes with the molecular formulas shown.

C6H12 C6H14 C22H46 C3H8

A B C D

(a) Give the IUPAC name of an alkane that could be A.

___________________________________________________________________
(1)

(b) Draw skeletal formulas for two branched-chain isomers of B.

State the type of isomerism shown.

Isomer 1

Isomer 2

Type of isomerism ____________________________________________

(3)

(c) Thermal cracking of one molecule of C can form one molecule of B and two
molecules of another organic compound.

The reaction occurs at a high temperature.

Write an equation for this reaction.

State one other reaction condition needed.

Equation

___________________________________________________________________

Reaction condition ___________________________________________________

(2)

Page 2 of 50
 (d) Under different conditions, catalytic cracking of C can occur as shown.

C22H46 → 2C5H10 + C6H12 + C6H14

C A B

Name the catalyst used.

___________________________________________________________________
(1)

D reacts with bromine gas in UV light or bright sunlight in the same way as methane
reacts with chlorine. The reaction is a free-radical substitution.

(e) Write an equation for the initiation step of this reaction.

___________________________________________________________________
(1)

(f) Write an equation to show the formation of a hydrocarbon in a termination step for
the reaction of D with bromine gas in UV light.

___________________________________________________________________
(1)
(Total 9 marks)

Q2.
Many fuels belong to the homologous series of alkanes.

(a) Compounds in a homologous series can be represented by the same general

formula.

Give two other characteristics of a homologous series.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(b) Write an equation to show the incomplete combustion of the alkane pentane,
forming carbon monoxide and water only.

___________________________________________________________________
(1)

Page 3 of 50
 (c) Catalytic converters are used to remove the NO and CO formed in petrol engines.

Write an equation to show the reaction that occurs in a catalytic converter to remove
these gases.

___________________________________________________________________
(1)

(d) When fossil fuels are burned in power stations sulfur dioxide is formed.

• Give one reason why sulfur dioxide is removed.

• Identify a compound that could be used to remove sulfur dioxide.
• State the type of reaction that occurs when sulfur dioxide is removed.

Reason ____________________________________________________________

___________________________________________________________________

Compound _________________________________________________________

Type of reaction _____________________________________________________

(3)
(Total 7 marks)

Q3.
Isomers of octane are hydrocarbons used in motor fuels.

(a) Name the process used to obtain kerosene from crude oil.

___________________________________________________________________
(1)

(b) Octane can be produced by catalytic cracking of kerosene.

Identify the catalyst and state the temperature used in this process.

Write an equation to show the cracking of one molecule of pentadecane (C 15H32) to

form octane and one other product.

Use molecular formulas in your equation.

Catalyst __________________________________________________________

Temperature _______________________________________________________

Equation

___________________________________________________________________
(3)

(c) 2,2,4-trimethylpentane is an isomer of octane used in motor fuels.

Draw the skeletal formula of 2,2,4-trimethylpentane.

(1)

Page 4 of 50
 (d) Write an equation to show the incomplete combustion of 2,2,4-trimethylpentane to
form carbon monoxide and water only.

Use molecular formulas in your equation.

___________________________________________________________________
(1)

(e) Carbon monoxide is removed using a catalytic converter.

Write an equation to show how the carbon monoxide reacts to form less harmful
products in the catalytic converter.

___________________________________________________________________
(1)

(f) Explain how a catalyst works.

___________________________________________________________________

___________________________________________________________________
(2)
(Total 9 marks)

Q4.
Difluoromethane (CH2F2) and trifluoromethane (CHF3) are used as refrigerants.

(a) Fluorine can react with difluoromethane to form trifluoromethane.

Give one essential condition for this reaction and name the mechanism.

Condition __________________________________________________________

Name of mechanism _________________________________________________

(2)

(b) Write an equation for each of the following steps in the mechanism for this reaction.

Initiation step

___________________________________________________________________

First propagation step

___________________________________________________________________

Second propagation step

___________________________________________________________________

Page 5 of 50
 A termination step

__________________________________________________________________

(4)
(Total 6 marks)

Q5.
Alkanes undergo combustion reactions and substitution reactions.

(a) Write an equation for the complete combustion of octane.

___________________________________________________________________
(1)

(b) State why the complete combustion of octane may contribute to environmental
problems.

___________________________________________________________________

___________________________________________________________________
(1)

(c) The skeletal formula of an isomer of octane is shown.

Give the IUPAC name for this isomer.

___________________________________________________________________
(1)

(d) Explain why the isomer of octane shown in part (c) has a lower boiling point than
octane.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

Page 6 of 50
The skeletal formula of compound Y is shown.

Y reacts with chlorine in a free radical substitution reaction.

(e) State what is meant by the term free radical.

___________________________________________________________________

___________________________________________________________________
(1)

(f) Give an equation for each of the propagation steps in the free radical reaction of Y
(C6H14) with chlorine to form C6H13Cl

You should use molecular formulae in your equations.

Propagation step 1

___________________________________________________________________

Propagation step 2

___________________________________________________________________
(2)

(g) Deduce the number of position isomers that can be formed when Y reacts with
chlorine to form C6H12Cl2

Tick (✓) one box.

4 5 6 7

(1)
(Total 9 marks)

Page 7 of 50
Q6.
The following pairs of compounds can be distinguished by simple test-tube reactions.

Give a reagent, or combination of reagents, that can be added to the compounds in each
pair to distinguish between them.
State what is observed in each case.

(a) Hexane and hex-2-ene.

Reagent ___________________________________________________________

Observation with hexane ______________________________________________

Observation with hex-2-ene ____________________________________________

(3)
(Total 14 marks)

Q7.
This question is about pentadecane, C15H32

(a) Write an equation to show the incomplete combustion of pentadecane to form

carbon monoxide as the only carbon-containing product.

___________________________________________________________________
(1)

(b) Nitrogen monoxide is also formed during the combustion of pentadecane in motor
vehicles.

Describe how nitrogen monoxide is formed.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(c) Write an equation to show how nitrogen monoxide is removed by a catalytic

converter.

___________________________________________________________________
(1)

Page 8 of 50
 (d) When pentadecane is used as a fuel in industry, sulfur-containing impurities cause
the formation of sulfur dioxide and other combustion products.

Explain how sulfur dioxide can be removed from these other combustion products.
Include an equation in your answer.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(e) Pentadecane can be converted into other useful molecules by cracking.

State the conditions needed for the cracking of pentadecane to form a high
proportion of aromatic hydrocarbons.

___________________________________________________________________

___________________________________________________________________
(2)

(f) Write an equation showing one molecule of pentadecane being cracked into hexane,
propene and one other product.

___________________________________________________________________
(1)
(Total 9 marks)

Q8.
Dodecane (C12H26) is a hydrocarbon found in the naphtha fraction of crude oil. Dodecane
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 dodecane.

Page 9 of 50
(a) Name the homologous series that both C2H4 and C4H8 belong to.
Draw a functional group isomer of C4H8 that does not belong to this homologous
series.

Name _____________________________________________________________

Functional group isomer

(2)

(b) Identify compound X.

___________________________________________________________________
(1)

(c) Name polymer Y.

___________________________________________________________________
(1)

(d) Reaction 1 is an example of thermal cracking and is carried out at a temperature of

750 °C.

State one other reaction condition needed.

___________________________________________________________________
(1)

(e) Reaction 2 is exothermic. A typical compromise temperature of 200 °C is used

industrially for this reaction.

Explain the effect of a change of temperature on both the position of equilibrium and
the rate of reaction, and justify why a compromise temperature is used industrially.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(6)
(Total 11 marks)

Page 10 of 50
Q9.
Which molecule is not produced when ethane reacts with bromine in the presence of
ultraviolet light?

A C2H4Br2

B HBr

C H2

D C4H10

(Total 1 mark)

Q10.
Some oil-fired heaters use paraffin as a fuel.
One of the compounds in paraffin is the straight-chain alkane, dodecane (C12H26).

(a) Give the name of the substance from which paraffin is obtained.
State the name of the process used to obtain paraffin from this substance.

Substance __________________________________________________________

Process ____________________________________________________________
(2)

(b) The combustion of dodecane produces several products.

Write an equation for the incomplete combustion of dodecane to produce gaseous

products only.

___________________________________________________________________
(1)

(c) Oxides of nitrogen are also produced during the combustion of paraffin in air.

(i) Explain how these oxides of nitrogen are formed.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(ii) Write an equation to show how nitrogen monoxide in the air is converted into
nitrogen dioxide.

______________________________________________________________
(1)

Page 11 of 50
 (iii) Nitric acid (HNO3) contributes to acidity in rainwater.

Deduce an equation to show how nitrogen dioxide reacts with oxygen and
water to form nitric acid.

______________________________________________________________
(1)

(d) Dodecane (C12H26) can be cracked to form other compounds.

(i) Give the general formula for the homologous series that contains dodecane.

______________________________________________________________
(1)

(ii) Write an equation for the cracking of one molecule of dodecane into equal
amounts of two different molecules each containing the same number of
carbon atoms.
State the empirical formula of the straight-chain alkane that is formed.
Name the catalyst used in this reaction.

Equation ______________________________________________________

Empirical formula of alkane ________________________________________

Catalyst _______________________________________________________

______________________________________________________________
(3)

(iii) Explain why the melting point of dodecane is higher than the melting point of
the straight-chain alkane produced by cracking dodecane.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(e) Give the IUPAC name for the following compound and state the type of structural
isomerism shown by this compound and dodecane.

IUPAC name ________________________________________________________

Type of structural isomerism ____________________________________________

(2)

Page 12 of 50
 (f) Dodecane can be converted into halododecanes.

Deduce the formula of a substance that could be reacted with dodecane to produce
1-chlorododecane and hydrogen chloride only.

___________________________________________________________________
(1)
(Total 16 marks)

Q11.
The following table shows the boiling points of some straight-chain alkanes.

CH4 C2H6 C3H8 C4H10 C5H12

Boiling point / °C −162 −88 −42 −1 36

(a) State a process used to separate an alkane from a mixture of these alkanes.

___________________________________________________________________
(1)

(b) Both C3H8 and C4H10 can be liquefied and used as fuels for camping stoves.

Suggest, with a reason, which of these two fuels is liquefied more easily.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(c) Write an equation for the complete combustion of C 4H10

___________________________________________________________________
(1)

(d) Explain why the complete combustion of C4H10 may contribute to environmental
problems.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(e) Balance the following equation that shows how butane is used to make the
compound called maleic anhydride.

..........CH3CH2CH2CH3 + .......... O2 ..........C2H2(CO)2O + .......... H2O

(1)

Page 13 of 50
(f) Ethanethiol (C2H5SH), a compound with an unpleasant smell, is added to gas to
enable leaks from gas pipes to be more easily detected.

(i) Write an equation for the combustion of ethanethiol to form carbon dioxide,
water and sulfur dioxide.

______________________________________________________________
(1)

(ii) Identify a compound that is used to react with the sulfur dioxide in the products
of combustion before they enter the atmosphere.

Give one reason why this compound reacts with sulfur dioxide.

Substance ____________________________________________________

Reason _______________________________________________________

______________________________________________________________
(2)

(iii) Ethanethiol and ethanol molecules have similar shapes.

Explain why ethanol has the higher boiling point.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(g) The following compound X is an isomer of one of the alkanes in the table on above.

(i) Give the IUPAC name of X.

______________________________________________________________
(1)

(ii) X has a boiling point of 9.5 °C.

Explain why the boiling point of X is lower than that of its straight-chain isomer.

______________________________________________________________

______________________________________________________________

Page 14 of 50
 ______________________________________________________________

______________________________________________________________
(2)

(iii) The following compound Y is produced when X reacts with chlorine.

Deduce how many other position isomers of Y can be formed.

Write the number of other position isomers in this box.

(1)

(h) Cracking of one molecule of an alkane Z produces one molecule of ethane, one
molecule of propene and two molecules of ethene.

(i) Deduce the molecular formula of Z.

______________________________________________________________
(1)

(ii) State the type of cracking that produces a high proportion of ethene and
propene.
Give the two conditions for this cracking process.

Type of cracking ________________________________________________

Conditions _____________________________________________________

______________________________________________________________
(2)
(Total 17 marks)

Q12.
Compound X is shown below. It is a member of a homologous series of hydrocarbons.

(a) (i) Deduce the general formula of the homologous series that contains X.

______________________________________________________________
(1)

Page 15 of 50
 (ii) Name a process used to obtain a sample of X from a mixture containing other
members of the same homologous series.

______________________________________________________________
(1)

(b) There are several isomers of X.

(i) Give the IUPAC name of the position isomer of X.

______________________________________________________________
(1)

(ii) Draw the structure of a functional group isomer of X.

(1)

(c) At high temperatures, one molecule of C15H32 can be converted into two molecules
of X and one molecule of another compound.

(i) Write an equation for this reaction.

______________________________________________________________
(1)

(ii) State the name of the process used to obtain a high yield of X from C15H32
Give one reason why this process is used in industry.

Name _________________________________________________________

Reason _______________________________________________________

______________________________________________________________
(2)

(iii) State why high temperatures are needed for this process.

______________________________________________________________

______________________________________________________________
(1)

Page 16 of 50
(d) Compound X can be converted into compound Y.
Compound Y is shown below.

(i) Suggest the formula of a reagent that could be added to X in order to convert
it into Y.

______________________________________________________________
(1)

(ii) Give one use of Y.

______________________________________________________________
(1)

(iii) Write an equation to show the reaction of Y in a limited supply of air to produce
a solid and water only.

______________________________________________________________
(1)

(iv) When a sample of Y, contaminated with CH3SH, is burned completely in air, a

toxic gas is formed.
Identify this toxic gas and suggest a compound that could be used to remove
the toxic gas from the products of combustion.

Toxic gas ______________________________________________________

Compound used to remove toxic gas ________________________________

______________________________________________________________
(2)

(v) Suggest the name of the process that occurs when the toxic gas in part (d)(iv)
is removed.

______________________________________________________________
(1)

(e) Explain why the boiling points of X and Y are similar.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(Total 16 marks)

Page 17 of 50
Q13.
Hexane (C6H14) is a member of the homologous series of alkanes.

(a) (i) Name the raw material from which hexane is obtained.

______________________________________________________________
(1)

(ii) Name the process used to obtain hexane from this raw material.

______________________________________________________________
(1)

(b) C6H14 has structural isomers.

(i) Deduce the number of structural isomers with molecular formula C 6H14

Write the number in this box.

(Space for working)

(1)

(ii) State one type of structural isomerism shown by the isomers of C 6H14

______________________________________________________________
(1)

(c) One molecule of an alkane X can be cracked to form one molecule of hexane and
two molecules of propene.

(i) Deduce the molecular formula of X.

______________________________________________________________

______________________________________________________________
(1)

(ii) State the type of cracking that produces a high percentage of alkenes. State
the conditions needed for this type of cracking.

Type of cracking ________________________________________________

Conditions _____________________________________________________

______________________________________________________________
(2)

(iii) Explain the main economic reason why alkanes are cracked.

Page 18 of 50
 ______________________________________________________________

______________________________________________________________
(1)

(d) Hexane can react with chlorine under certain conditions as shown in the following
equation.

C6H14 + Cl2 C6H13Cl + HCl

(i) Both the products are hazardous. The organic product would be labelled
‘flammable'.
Suggest the most suitable hazard warning for the other product.

______________________________________________________________
(1)

(ii) Calculate the percentage atom economy for the formation of C6H13Cl (Mr =
120.5) in this reaction.

______________________________________________________________

______________________________________________________________
(1)

(e) A different chlorinated compound is shown below. Name this compound and state
its empirical formula.

Name ____________________________________________________________

Empirical formula ___________________________________________________

(2)
(Total 12 marks)

Page 19 of 50
Q14.
(a) There is a risk of gas explosions in coal mines. This risk is mainly due to the
presence of methane. If the percentage of coal-mine methane (CMM) in the air in
the mine is greater than 15%, the explosion risk is much lower. CMM slowly
escapes from the mine into the atmosphere.

Write an equation to show the complete combustion of methane.

Suggest one reason why there is a much lower risk of an explosion if the
percentage of CMM is greater than 15%.

State why it is beneficial to the environment to collect the CMM rather than allowing
it to escape into the atmosphere.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(b) Methane can be obtained from crude oil. Some of this crude oil contains an impurity
called methanethiol (CH3SH). This impurity causes environmental problems when
burned.

Write an equation to show the complete combustion of methanethiol.

State why calcium oxide can be used to remove the sulfur-containing product of this
combustion reaction.

State one pollution problem that is caused by the release of this sulfur-containing
product into the atmosphere.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)
(Total 6 marks)

Page 20 of 50
Q15.
Pentane is a member of the alkane homologous series.

(a) Give the general formula for the homologous series of alkanes.

___________________________________________________________________
(1)

(b) One of the structural isomers of pentane is 2,2-dimethylpropane.

Draw the displayed formula of 2,2-dimethylpropane.

State the type of structural isomerism shown.

___________________________________________________________________
(2)

(c) A molecule of hydrocarbon Y can be thermally cracked to form one molecule of

pentane and two molecules of ethene only.

Deduce the molecular formula of Y.

State why high temperatures are necessary for cracking reactions to occur.

Give one reason why thermal cracking reactions are carried out in industry.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

Page 21 of 50
(d) Write an equation for the incomplete combustion of pentane to form a solid
pollutant.

Suggest why this solid pollutant is an environmental problem.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(e) Pentane can react with chlorine as shown in the following equation.

C5H12 + Cl2 → C5H11Cl + HCl

Calculate the percentage atom economy for the formation of C 5H11Cl

Deduce how many straight-chain isomers of C5H11Cl could be formed.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(f) Consider the following compound.

Name this compound.

Deduce the empirical formula of this compound.

___________________________________________________________________

___________________________________________________________________
(2)
(Total 13 marks)

Page 22 of 50
Q16.
(a) The reaction of bromine with propane is similar to that of chlorine with methane.
Three steps in the mechanism for the bromination of propane to form 1-
bromopropane are shown below.

Step 1 Br2 2Br•

Step 2 Br• + CH3CH2CH3 CH3CH2CH2• + HBr

Step 3 CH3CH2CH2• + Br2 CH3CH2CH2Br + Br•

(i) Name the type of mechanism in this reaction.

______________________________________________________________
(1)

(ii) Give an essential condition for Step 1 to occur.

______________________________________________________________
(1)

(iii) Name the type of step illustrated by Steps 2 and 3.

______________________________________________________________
(1)

(iv) In this mechanism, a different type of step occurs in which free radicals
combine. Name this type of step.
Write an equation to show how hexane could be formed from two free radicals
in the mechanism of this reaction.

Type of step ____________________________________________________

Equation ______________________________________________________
(2)

(v) Write an overall equation for the reaction between bromine and propane by
the same mechanism to produce octabromopropane (C 3Br8).

______________________________________________________________
(1)

Page 23 of 50
Q17.
There are several oxides of nitrogen.

(a) An oxide of nitrogen contains 25.9% by mass of nitrogen. Determine the empirical
formula of this oxide.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(b) Give one reason why the oxide NO is a pollutant gas.

___________________________________________________________________

___________________________________________________________________
(1)

(c) The oxide NO reacts with oxygen to form nitrogen dioxide. Write an equation for this
reaction.

___________________________________________________________________
(1)

(d) Explain how NO is produced in the engine of a motor vehicle.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(e) Write an equation to show how NO is removed from the exhaust gases in motor
vehicles using a catalytic converter.

___________________________________________________________________
(1)
(Total 8 marks)

Page 24 of 50
Q18.
The alkane butane is used as a fuel.

(a) (i) Write an equation for the complete combustion of butane.

______________________________________________________________
(1)

(ii) State a condition which may cause carbon to be formed as a product in the
combustion of butane.

______________________________________________________________
(1)

(b) Butane obtained from crude oil may contain trace amounts of an impurity.
When this impurity burns it produces a toxic gas that can be removed by reacting it
with calcium oxide coated on a mesh.

(i) Suggest the identity of the toxic gas.

______________________________________________________________
(1)

(ii) Suggest why calcium oxide reacts with the toxic gas.

______________________________________________________________
(1)

(iii) Suggest why the calcium oxide is coated on a mesh.

______________________________________________________________
(1)
(Total 5 marks)

Page 25 of 50
Q19.
Pent-1-ene is a member of the alkene homologous series.

(a) Pent-1-ene can be separated from other alkenes.

State the physical property of alkenes that allows them to be separated from a
mixture by fractional distillation.

___________________________________________________________________
(1)

(b) (i) State the meaning of the term structural isomerism.

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(ii) Name the branched chain isomer of pent-1-ene shown below.

______________________________________________________________
(1)

(iii) Draw the structure of a functional group isomer of pent-1-ene.

(1)

(c) The cracking of one molecule of compound X produces pent-1-ene, ethene and
butane in a 1:2:1 mol ratio.
Deduce the molecular formula of X and state a use for the ethene formed.

Molecular formula of X ________________________________________________

Use of ethene _______________________________________________________

(2)
(Total 7 marks)

Page 26 of 50
Q20.
Alkanes are saturated hydrocarbons which can be obtained from crude oil.
Pentane is an example of an alkane. A molecule of pentane contains five carbon atoms.

(a) (i) State the meaning of the term saturated and of the term hydrocarbon as
applied to alkanes.

Saturated ______________________________________________________

______________________________________________________________

Hydrocarbon ___________________________________________________

______________________________________________________________
(2)

(ii) Give the general formula for the alkanes.

______________________________________________________________
(1)

(b) Pentane burns completely in oxygen.

(i) Write an equation for this reaction.

____________________________________________________________
(1)

(ii) State how the products of this reaction may affect the environment.

______________________________________________________________

______________________________________________________________
(1)

(c) Give the name of a solid pollutant which may form when pentane burns
incompletely in air.

___________________________________________________________________
(1)

(d) One molecule of C9H20 can be cracked to form one molecule of pentane and one
other product.

(i) Write an equation for this cracking reaction.

______________________________________________________________
(1)

(ii) Suggest a type of compound that can be manufactured from the other product
of this cracking reaction.

______________________________________________________________
(1)

Page 27 of 50
 (iii) State why a high temperature is needed for cracking reactions to occur.

______________________________________________________________

______________________________________________________________
(1)

(e) Pentane can react to form the following haloalkane Q.

(i) Name Q.

______________________________________________________________
(1)

(ii) State the type of structural isomerism shown by Q and the haloalkane shown
below.

______________________________________________________________
(1)
(Total 11 marks)

Page 28 of 50
Mark schemes

Q1.
(a) Cyclohexane
Accept branched cyclic alkanes eg
methylcyclopentane or dimethlycyclobutane.
1

(b) Any two of:

Structural
1

(c) C22H46 ⟶ C6H14 + 2 C8H16

1

P > 1000 kPa / 10 atm

1

(d) Aluminosilicate / zeolite

1

(e) Br−Br ⟶ 2Br•

1

(f) C3H7• + C3H7• ⟶ C6H14

1
[9]

Q2.
(a) Any two from:

• show a gradation / trend / gradual change in physical properties / a

specified property

• differ by CH2

• chemically similar or react in the same way

• have the same functional group

2

Page 29 of 50
 (b) C5H12 + 5½ O2 ⟶ 5 CO + 6 H2O
Accept multiples
1

(c) 2NO + 2CO ⟶ N2 + 2CO2

Accept multiples
1

(d) Why SO2 removed: toxic / dissolves in water to form acid rain
1

Compound: CaO / lime / CaCO3 / limestone

Allow acid-base reaction
1

Process: neutralisation
Ignore flue gas desulfurisation
1
[7]

Q3.
(a) Fractional distillation
1

(b) Zeolite / aluminosilicate catalyst

Allow silicon oxide and aluminium oxide
1

700-800 K or 427-527 °C
Allow value in range
Units needed
Ignore pressure
1

C15H32 ⟶ C8H18 + C7H14

1

(c)

(d) C8H18 + 8½ O2 ⟶ 8 CO + 9 H2O

Ignore state symbols
Allow multiples
Allow (CH3)3CCH2CH(CH3)2 + 8½ O2 ⟶ 8 CO + 9
H2O
1

(e) CO + NO ⟶ CO2 + ½ N2

Page 30 of 50
 Ignore state symbols
Allow multiples
1

(f) Provides an alternative route

Alternative reaction pathway
1

Lower Activation Energy

1
Allow answers in terms of adsorption /
desorption, but do not allow mix and match
answers
M1: gases adsorb onto active sites
M2: weakens bonds.
Ignore surface area
Implication that catalyst doesn’t change rate CE
=0
[9]

Q4.
(a) uv light
1

(Free) Radical substitution

1

(b) (initiation)
Allow radical dot anywhere on particles

F2 ⟶ 2F•
1

(first propagation)
CH2F2 + F• ⟶ •CHF2 + HF
1

(second propagation)
•CHF2 + F2 ⟶ CHF3 + F•
1

(termination)
2 •CHF2 ⟶ CHF2CHF2 or •CHF2 + F• ⟶ CHF3 or 2F• ⟶ F2
Allow 2 •CHF2 ⟶ C2H2F4
1
[6]

Q5.
(a) C8H18 + 12½ O2 ⟶ 8CO2 + 9H2O
Ignore ss
Accept multiple
1

(b) CO2 / H2O evolved contributes to / causes global warming

Page 31 of 50
 Ignore climate change
Accept CO2 / H2O evolved is a greenhouse gas /
The products formed are greenhouse gases

The products formed contribute to global warming

1

(c) (2,2,3,3)- tetramethylbutane

1

(d) Because molecule is less polarisable / lower surface area / more spherical
Allow molecule is smaller
1

Weaker van der Waals forces between molecules

CE = 0 if bond breaking mentioned
Allow converse answers which refer to straight
chain isomers
1

(e) Species with an unpaired electron

Do not allow ion; free electron; non bonded
electron
1

(f) Step 1:
C6H14 + Cl• ⟶ •C6H13 + HCl
1
Step 2:
•
C6H13 + Cl2 ⟶ C6H13Cl + Cl•
Ignore ss
Accept multiple
Dot allowed anywhere on radical
Allow skeletal formulae?
1

(g) 7 / tick in 4th box

Automarked
1
[9]

Q6.
(a) Reagent: Bromine (water) / Br2(aq)
If no/incorrect reagent, then CE = 0
If incomplete reagent (e.g Br) do not award but
mark on.
Credit alternative reagents such as iodine /
acidified KMnO4
1

Hexane: no visible change / no change / stays orange

Allow no reaction
Do not allow none, nothing, clear, no observation
Penalise ppt etc.
1

Page 32 of 50
 Hex-2-ene: (bromine) turns colourless (from orange)
Allow decolourised
1

(b) Reagent: Tollens’ Reagent / ammoniacal silver nitrate

If no/ incorrect reagent, then CE = 0
If incomplete reagent (e.g. formula of complex
ion) do not award but mark on.
Credit alternative reagents such as acidified
K2Cr2O7 / acidified KMnO4 etc.
1

Propanone: no visible change / no change

Allow no reaction
Do not allow none, nothing, clear, no observation
1

Propanal: silver mirror formed / grey solid / black ppt

OR

Reagent: Fehling’s Solution / Benedict’s Solution

Propanone: no visible change / no change / (solution) remains blue

Allow no reaction
Do not allow none, nothing, clear
Allow orange ppt

Propanal: red ppt

1

(c) Reagent: acidified (dil H2SO4) K2Cr2O7

If no / incorrect reagent, then CE = 0
If incomplete reagent (such as ion or missing
acid) do not award but mark on.
Penalise ppt etc.
1

Propan-2-ol: solution turns from orange to green

1

2-Methylpropan-2-ol: no visible change / solution remains orange

Allow no reaction
Do not allow none, nothing, clear, no observation

OR

Reagent: acidified (dil H2SO4) KMnO4

Propan-2-ol: solution turns from purple to colourless

2-Methylpropan-2-ol: no visible change / solution remains purple

Allow no reaction
Do not allow none, nothing, clear
1

(d) Reagent: AgNO3

Page 33 of 50
 1

If no / incorrect reagent, then CE = 0

If incomplete reagent (such as ion or missing acid) do not award but mark on.
Must show all bonds
1

iodoethane: yellow ppt formed

Ignore rate of formation; Apply List
1

Ethanoic acid: no visible change

Allow no reaction
Do not allow none, nothing, clear

OR

Reagent: Na2CO3 / any named carbonate/hydrogencarbonate / any named

reactive metal (e.g. Na)

Iodoethane; no visible change

Allow no reaction
Do not allow none, nothing, clear

Ethanoic acid: effervescence

Allow gas formed
Penalise wrong gas
1

(e) Relative molecular mass of pentane:

72.1416
2 d.p. or more
1

Relative molecular mass of butanal:

72.1002
2 d.p. or more
1
[14]

Q7.

(a) C15H32 + 15 O2 ⟶ 15CO + 16H2O

Allow multiples
Ignore state symbols
1

(b) Nitrogen and oxygen (from air) react

Allow correct equation
1

At high temperatures
Allow temperatures about 1000 °C/spark

Page 34 of 50
 Not just heat/hot/heat from engine
M2 dependent on M1
1

(c) NO + CO ⟶ N2 + CO2
Allow multiples
Ignore state symbols
1

(d) CaO/lime/CaCO3/limestone
Allow M1 scored from equation even if incorrect.
Equation scores 2 marks
1

CaCO3 + SO2 ⟶ CaSO3 + CO2

OR
CaO + SO2 ⟶ CaSO3
Or via two equations:
CaCO3 ⟶ CaO + CO2
CaO + SO2 ⟶ CaSO3
1
Allow

SO2 + CaO + O2 ⟶ CaSO4

SO2 + CaO + 2H2O + O2 ⟶ CaSO4 + 2H2O

SO2 + CaCO3 + O2 ⟶ CaSO4 + CO2

(e) High temperature/700−800 K/450 °C

Ignore pressure
1

Zeolite catalyst/aluminosilicate
Apply list principle
“Catalyst” by itself is insufficient
1

(f) C15H32 ⟶ C6H14 + C3H6 + C6H12

Allow multiples
Ignore state symbols
1
[9]

Q8.
(a) Alkenes
1

Page 35 of 50
 Correctly drawn molecule of cyclobutane or methyl
cyclopropane, need not be displayed formula
1

(b) C6H14 (or correct alkane structure with 6 carbons)

Allow hexane or any other correctly named alkane with 6
carbons
1

(c) Poly(but-2-ene)
1

(d) High pressure

Allow pressure ࣙ MPa
Mention of catalyst loses the mark
1

(e) This question is marked using levels of response. Refer to the Mark Scheme
Instructions for Examiners for guidance on how to mark this question.

Level 3

All stages are covered and the explanation of each stage is generally correct
and virtually complete.

Answer communicates the whole process coherently and shows a logical

progression from stage 1 and stage 2 (in either order) to stage 3.
5–6 marks

Level 2

All stages are covered but the explanation of each stage may be incomplete or
may contain inaccuracies OR two stages are covered and the explanations
are generally correct and virtually complete.

Answer is mainly coherent and shows progression. Some steps in each stage
may be out of order and incomplete.
3–4 marks

Level 1

Two stages are covered but the explanation of each stage may be incomplete
or may contain inaccuracies, OR only one stage is covered but the
explanation is generally correct and virtually complete.

Answer includes isolated statements but these are not presented in a logical
order or show confused reasoning.
1–2 marks

Level 0

Page 36 of 50
 Insufficient correct chemistry to gain a mark.
0 marks
Indicative chemistry content
Stage 1: consider effect of higher temperature on yield
(Or vice versa for lower temperature)
• Le Chatelier’s principle predicts that equilibrium shifts
to oppose any increase in temperature
• Exothermic reaction, so equilibrium shifts in
endothermic direction / to the left
• So a Higher T will reduce yield
Stage 2: consider effect of higher temperature on rate
(Or vice versa for lower temperature)
• At higher temperature, more high energy molecules
• more collisions have E>Ea
• So rate of reaction increases / time to reach
equilibrium decreases
Stage 3: conclusion
Industrial conditions chosen to achieve (cost-effective)
balance of suitable yield at reasonable rate
[11]

Q9.
C
[1]

Q10.
(a) Crude oil OR petroleum
Not petrol.
1

Fractional distillation / fractionation

Not distillation alone.
1

(b) C12H26 + 12.5O2 12CO + 13H2O

Allow balanced equations that produce CO 2 in addition to
CO.
Accept multiples.
1

(c) (i) M1 Nitrogen and oxygen (from air) react / combine / allow a correct
equation
If nitrogen from petrol / paraffin / impurities CE = 0 / 2.
1

M2 at high temperatures
Allow temperatures above 1000 °C or spark.
Not just heat or hot.
M2 dependent on M1.
But allow 1 mark for nitrogen and oxygen together at high

Page 37 of 50
 temperatures.
1

(ii) 2NO + O2 2NO2

Allow multiples.
1

(iii) 4NO2 + 2H2O + O2 4HNO3

Allow multiples.
1

(d) (i) CnH2n+2

Allow CxH2x+2

CnH2n+2
Allow CxH2x+2
1

(ii) C12H26 C6H14 + C6H12

Only.
1

C3H7
Only.
1

Zeolite / aluminosilicate(s)
Ignore aluminium oxide.
1

(iii) Larger molecule / longer carbon chain / more electrons / larger surface
area
1

More / stronger van der Waals’ forces between molecules

Allow dispersion forces / London forces / temporary induced
dipole-dipole forces between molecules.
If breaking bonds, CE = 0 / 2.
1

(e) 2,2,3,3,4,4-hexamethylhexane
Only.
Ignore punctuation.
1

Chain
Ignore branch(ed).
1

(f) Cl2
Only.

Cl–Cl
Not CL2 or Cl2 or CL2 or Cl2 or CL2.
Ignore Chlorine.
1

Page 38 of 50
 [16]

Q11.
(a) Fractional distillation / fractionation / GLC / gas liquid chromatography
1

(b) C4H10
Need C4H10 and the reason for the mark

Because it has a higher bp / has stronger IMF / larger molecule / longer chain /
larger surface (area)
1

(c) C4H10 + 6½ O2 4CO2 + 5H2O

Accept multiples
Ignore state symbols
1

(d) CO2 or H2O evolved is a greenhouse gas / CO2 or H2O evolved contribute to
global warming / the products are greenhouse gases
Ignore climate change
1

(e) CH3CH2CH2CH3 + 3.5O2 C2H2(CO)2O + 4H2O

Accept multiples
Allow with or without a number 1 before the organic
molecules
1

(f) (i) C2H5SH + 4.5O2 2CO2 + 3H2O + SO2

Accept multiples
1

(ii) Calcium oxide / calcium carbonate

Allow any base or alkali
Allow correct formulae
1

Neutralises the SO2 / acid base reaction / it is a base

Can only score M2 if base or alkali used in M1
Allow M2 if blank in M1
1

(iii) Ethanol contains hydrogen bonding

Breaking covalent bonds CE = 0 / 2

Which is stronger than IMF (VDW / dipole-dipole forces) in ethanethiol /

(H bonding) is the strongest IMF
Only award M2 if M1 given, but allow IMF in ethanol are
stronger than in ethanethiol for maximum 1 mark
1

(g) (i) (2,2-)dimethylpropane

Ignore punctuation
1

Page 39 of 50
 (ii) Because molecule is smaller / less polarisable / has less surface (area) /
is more spherical / molecules can’t get as close to one another (to feel
the vdW forces)
Allow converse answers referring to straight chain isomers
CE = 0 / 2 if breaking bonds
1

vdW intermolecular forces or vdW force between molecules are weaker

or fewer
Need vdW rather than just IMF
1

(iii) 1 or one
1

(h) (i) C9H20

H20C9
1

(ii) Thermal (cracking)

If not thermal cracking CE = 0 / 2
1

High pressure AND high temperature

If blank mark on
Allow high P and T
1

OR

Pressure of ≥ 10 atm, ≥ 1 MPa ≥ 1000 kPa

AND temp of 400 °C ≤ T ≤ 1000 °C or 650 K ≤ T≤ 1300 K

Do not allow high heat
If no units for T, then range must be 650 − 1000
1
[17]

Q12.
(a) (i) CnH2n / CxH2x
1

(ii) Fractional distillation / GLC / gas liquid chromatography / fractionation

Do not allow cracking / distillation
1

(b) (i) But-1-ene / but1ene

Ignore hyphens and commas
Do not allow butene-1 / but-2-ene / butane / butane /alkene /
C4H8 / propene / straight-chain alkene
1

(ii) A structure of cyclobutane or

methyl-cyclopropane
Allow skeletal formula.
1

Page 40 of 50
(c) (i) C15H32 → 2C4H8 + C7H16
Do not accept multiples.
1

(ii) Thermal cracking

Not catalytic cracking or cracking.
1

To produce products that are in greater demand / more valuable / more

expensive / more profitable
The (unsaturated) alkene or the (unsaturated) molecule or X
produced can be polymerised or can be made into plastics.
Ignore more useful products.
1

(iii) Break (C–C or C–H) bonds

Allow to overcome the activation energy.
Allow to break the carbon chain.
Penalise breaking wrong bonds.
1

(d) (i) H2
Only.
1

(ii) Fuel / LPG

Allow camping gas, lighter fuel, propellant, refrigerant,
cordless appliances.
Do not allow petrol or motor fuel.
Ignore natural gas.
1

(iii) C4H10 + 2.5O2 → 4C + 5H2O

Accept multiples.
1

(iv) SO2 / sulfur dioxide

If other sulfur oxides, mark on.
1

Calcium oxide / CaO / lime / quicklime

Allow CaCO3 / allow Ca(OH)2 or names.
Allow any solid base.
M2 dependent on M1.
Do not allow limewater.
1

(v) Neutralisation
Allow acid-base reaction.
Allow flue gas desulfurisation / FGD
1

(e) (Molecules) are similar sizes / have similar Mr / have similar number of electrons
Chemical error CE = 0/2 if breaking bonds.

Page 41 of 50
 Allow similar number of carbon and hydrogen atoms / similar
surface area / similar chain length.
Can accept same number of carbon atoms.
Do not accept same number of H atoms / same number of
bonds.
Ignore similar amount of bonds.
1

Similar van der Waals forces between molecules / similar intermolecular forces
(IMF)
Not similar incorrect IMF eg dipole-dipole
1
[16]

Q13.
(a) (i) Crude oil / oil / petroleum
Do not allow ‘petrol’
1

(ii) Fractional distillation / fractionation / fractionating

Not distillation alone
1

(b) (i) 5
Allow five / V
1

(ii) Chain (isomerism)

Allow branched chain / chain branched / side chain
(isomerism)
Ignore position (isomerism)
Do not allow straight chain / geometric / branched / function
1

(c) (i) C12H26 / H26C12

Only
1

(ii) Thermal cracking

If not thermal cracking, CE = 0/2
If blank mark on
1

High temperature
Allow ‘high heat’ for ‘high temperature’

(400°C < T < 900°C) or (650 K < T < 1200 K)

Not ‘heat’ alone
If no T, units must be 650 – 900

and

High pressure (> 10 atm, > 1 MPa, >1000 kPa)

1

Page 42 of 50
 (iii) To produce substances which are (more) in demand / produce products with a
high value / products worth more
Ignore ‘to make more useful substances’
1

(d) (i) Corrosive or diagram to show this hazard symbol

Ignore irritant, acidic, toxic, harmful
1

(ii) ( 120.5 × 100)

(86 + 71 )

=76.75(%) or 76.8(%)
Allow answers > 3 sig figs
1

(e) 2,2-dichloro-3–methylpentane
Ignore punctuation
Any order
1

C3H6Cl
1
[12]

Q14.
(a) CH4 + 2O2 → CO2 + 2H2O
Accept multiples
Ignore state symbols even if incorrect
1

Not enough oxygen / air

1

CMM / methane is a greenhouse gas / contributes

to global warming
Do not allow formation of CO2 / CO2 is a greenhouse gas
Apply list principle, eg
CH4 is a greenhouse gas and toxic = 0
CH4 is a greenhouse gas and damages ozone = 0
Allow CH4 and CO2 are greenhouses gases
Allow collect to use as a fuel so fossil fuels do not run out (as
quickly)
1

(b) CH3SH + 3O2 → CO2 + 2H2O + SO2

Accept multiples
Ignore state symbols even if incorrect
1

Calcium oxide is basic (and SO2 is acidic) /

CaO neutralises SO2 /

Page 43 of 50
 CaO reacts with SO2 to form gypsum / salt / solid /
CaSO4 / CaSO3

Allow CaO + SO2 → CaSO3

M2 and M3 can only be scored if SO2 seen somewhere in
the answer
1

Acid rain
Allow consequence of acid rain eg increased rusting of iron /
fish in lakes die / problems for asthmatics
Apply list principle
Ignore air pollution
1
[6]

Q15.
(a) Cn H2n+2
Allow x in place of n
1

(b)

Chain
Must show every bond
Allow branched chain
2

(c) C9H20
Only
1

To break the (C-C and/or C-H) bonds

M2=0 if break C=C
1

To make products which are in greater demand / higher

value / make alkenes
Not more useful products
Allow specific answers relating to question
1

(d) C5H12 + 3O2 → 5C + 6H2O

Page 44 of 50
 Allow other balanced equations which give C and CO/CO 2
1

Causes global dimming / exacerbates asthma / causes

breathing problems / makes visibility poor / smog
Apply list principle
Ignore causes cancer / toxic
1

(e) (x 100)
1

74.48%
Allow 74.5%
1

3
Only
1

(f) 2,3-dichloro-3-methylpentane
Ignore punctuation
1

C3H6Cl
Only
1
[13]

Q16.
(a) (i) (Free-) radical substitution
Both words needed
1

(ii) UV light/Ultra-violet light/sunlight

OR high temperature/150 °C ≤ T ≤ 500 °C
1

(iii) Propagation (Step)

Ignore “first” or “second”
Accept phonetic spelling
1

(iv) M1 Termination (Step)

M2 2CH3CH2CH2• C6H14
In M2
C6H14 may be drawn out as CH3CH2CH2CH2CH2CH3
The dot may be anywhere around the terminal CH2 on the
radical
Accept C3H7• with dot anywhere
Penalise the absence of any radical dot
2

Page 45 of 50
 (v) C3H8 + 8Br2 C3Br8 + 8HBr
Or multiples
1

(b) (i) M1 Double bonds are

electron-rich

OR electron pair donors

OR centres of electron density.

M2 Bromine becomes polarised/becomes polar

OR forms an induced dipole

OR becomes δ+/δ–
M1 QoL – require one of these terms
Ignore “(very) negative” and “nucleophile” as applied to the
double bond.
Penalise M2 for ion formation from bromine
For M2, do not credit dipole formation solely as a
consequence of electronegativity
2

(ii) Electrophilic addition

Both words needed
Accept phonetic spelling
1

(iii) Structure for 1,2,4,5-tetrabromopentane, for example

BrCH2CHBrCH2CHBrCH2Br

OR

Must be clear that they have drawn 1,2,4,5-

tetrabromopentane and does NOT need to be displayed
Credit use of “sticks” for each C-H bond
1

(c) +

M1 Structure of CH3CHCH3

M2 (Secondary) Carbocation OR (secondary) carbonium ions

Mark independently
For M1 the positive charge must be on the central carbon
atom
Penalise bond to positive charge

Page 46 of 50
 Penalise answers which show more than the correct
carbocation e.g. the mechanism, unless the intermediate is
clearly identified
Credit use of “sticks” for each C-H bond
For M2, penalise “primary” or “tertiary”
2
[12]

Q17.
(a) O = 74.1%
1

If atomic numbers or molecular masses are used lose M2

1

1.85 4.63
1 2.5
N2O5
1
This ratio alone will not score the final mark. (It would get 2)
Allow 3 marks for N2O5

(b) Toxic/poisonous/forms an acidic gas/forms NO2 which is acidic/

respiratory irritant/forms HNO3 when NO reacts with water and oxygen/
triggers asthma attacks/greenhouse gas/photochemical smog/
contributes to global warming/formation of acid rain
ignore NO is an acidic gas or NO is acidic in water
Not references to ozone layer
1

(c) 2NO + O2 → 2NO2

Accept multiples or fractions of equation
Ignore wrong state symbols
1

(d) Nitrogen/N2 and oxygen/O2 combine/react

QWC (not N and O combine)
Not nitrogen in fuel
Allow N2 + O2 → 2NO for M1 only
1

spark/high temperature/2500-4000 °C
1

(e) 2NO + 2CO → N2 + 2CO2

OR

2NO → N2 + O2
Accept multiples or fractions of equation
Ignore wrong state symbols
Allow C8H18 + 25NO → 8CO2 + 12.5N2 + 9H2O
1

Page 47 of 50
 [8]

Q18.

(a) (i) C4H10 + 6 O2 → 4CO2 + 5H2O

Allow multiples
1

(ii) insufficient oxygen/low temperature/poor mixing of

butane and air
Allow insufficient air
Allow lack or oxygen/air
Do not allow no oxygen
Not incomplete combustion
1

(b) (i) Sulfur dioxide/SO2

Allow sulfur trioxide/SO3
(allow spelling of sulphur to be sulphur)
1

(ii) It is basic/the gas (SO2) is acidic

Idea of neutralisation
It = calcium oxide
1

(iii) bigger surface area to react

Do not allow cheaper
1
[5]

Q19.
(a) (Different) boiling points
Ignore mp’s, references to imf, different volatilities
1

(b) (i) Compound which have the same molecular formula

Accept same no and type of atom for M1
But If same (chemical) formula M1 = 0 but allow M2
If empirical formula CE = 0/2
1

but different structures/different structural

formulae/different displayed formulae
M2 dependent on M1
1

(ii) 3-methylbut-1-ene
only
ignore commas and hyphens
1

(iii)

Page 48 of 50
 Allow any correct structure with a cyclic alkane
1
Do not allow

i.e with an H missing on one C

(c) C13H28
only
1

Making plastics/used to make polymers or polythene/used

to make antifreeze/make ethanol/ripening fruit/any named
additional polymer
not used as a plastic/polymer/antifreeze
not just ‘polymers’ – we need to see that they are being
made
1
[6]

Q20.
(a) (i) single (C-C) bonds only/no double (C=C) bonds
1

Page 49 of 50
 Allow all carbon atoms bonded to four other atoms
Single C-H bonds only = 0
C=H CE

C and H (atoms) only/purely/solely/entirely

Not consists or comprises
Not completely filled with hydrogen
CH molecules = CE
Element containing C and H = CE
1

(ii) CnH2n+2
Formula only
CxH2x+2
1

(b) (i) C5H12 + 8O2 → 5CO2 + 6H2O

Accept multiples
Ignore state symbols
1

(ii) gases produced are greenhouse gases/contribute to Global

warming/effect of global warming/climate change
Allow CO2 or water is greenhouse gas/causes global
warming
Acid rain/ozone CE = 0
1

(c) carbon
Allow C
Allow soot
1

(d) (i) C9H20 → C5H12 + C4H8

OR

C9H20 → C5H12 + 2C2H4

Accept multiples
1

(ii) Plastics, polymers

Accept any polyalkene/haloalkanes/alcohols
1

(iii) so the bonds break OR because the bonds are strong

IMF mentioned = 0
1

(e) (i) 1,4-dibromo-1-chloropentane/1-chloro-1,4-dibromopentane

Ignore punctuation
1

(ii) Chain/position/positional
Not structural or branched alone
1
[11]

Page 50 of 50