Name: ________________________

3.3.2.1 Class: ________________________

Date: ________________________

Time: 166 minutes

Marks: 157 marks

Comments:

Rivers Academy West London Page 1 of 45

 The diagram shows a fractionating column used in the industrial fractional distillation of crude oil.
1.

Which statement is correct?

A The most viscous product is fuel oil.

B The boiling point of naphtha is higher than diesel oil.

C Molecules in diesel oil are held together by hydrogen bonds.

D Kerosene is a mixture of compounds.

(Total 1 mark)

This question is about poly(propene).

2.

Rivers Academy West London Page 2 of 45

(a) The three key steps in the manufacture of poly(propene) from crude oil are shown.

Naphtha is a mixture of alkanes with 6 to 12 carbon atoms per molecule.

For each step, name the process and state briefly the purpose of the process that leads to
the formation of poly(propene).

Step 1

Name _____________________________________________________________

Purpose ___________________________________________________________

___________________________________________________________________

___________________________________________________________________

Step 2

Name _____________________________________________________________

Purpose ___________________________________________________________

___________________________________________________________________

___________________________________________________________________

Step 3

Name _____________________________________________________________

Purpose ___________________________________________________________

___________________________________________________________________

___________________________________________________________________
(6)

(b) Poly(propene) is not biodegradable because it is unreactive.

Explain why poly(propene) is unreactive.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

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 (c) Scientists are developing new polymers, including some that are biodegradable.

Suggest why it is beneficial for some polymers to be biodegradable.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)
(Total 8 marks)

This question is about fuels.

3.
(a) The petrol fraction obtained from crude oil can be used as fuel in cars.

State the meaning of fraction, as used in the term petrol fraction.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(b) Hexadecane (C16H34) can be cracked at high temperature to form petrol.

Complete the equation to show the cracking of one molecule of hexadecane to form
hexane and cyclopentane only.

Give the name of a catalyst used in this cracking reaction.

C16H34 → _______________ + _______________

Catalyst ____________________________________________________________
(3)

(c) Carbon dioxide is formed when petrol is burned.

Carbon dioxide acts as a greenhouse gas when it absorbs infrared radiation.

Give a reason why carbon dioxide absorbs infrared radiation.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

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(d) Compound Z (HOCH2CH2NH2) can be used to remove carbon dioxide from the mixture of
waste gases produced in some power stations.

The figure below shows part of a suggested mechanism for the reaction of Z with carbon
dioxide.

Draw two curly arrows to complete the mechanism in the figure above.

Name compound Z (HOCH2CH2NH2)

Deduce the role of Z in step 2 of the mechanism.

Name _____________________________________________________________

Role ______________________________________________________________

___________________________________________________________________
(4)

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(e) HOCH2CH2NH2 can be represented as XNH2
[HOCH2CH2NH3]+ can be represented as [XNH3]+

Draw the shape of XNH2 and of [XNH3]+

State whether the H–N–H bond angle in XNH2 is greater than, the same as, or smaller than
that in [XNH3]+

Explain your answer.

Shape of XNH2 Shape of [XNH3]+

Bond angle _________________________________________________________

Explanation _________________________________________________________

___________________________________________________________________
(4)

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 (f) Bioethanol is used as an alternative to fossil fuels.

This statement appeared on a website.

“The fact that bioethanol is a carbon-neutral fuel outweighs the environmental

disadvantages of producing bioethanol.”

Evaluate this statement.

In your answer you should include:

• an outline of how bioethanol is produced
• relevant equations
• analysis of the environmental impacts.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(6)
(Total 19 marks)

Which statement is correct about the fractional distillation of crude oil?

4.
A A zeolite catalyst is used.

B Each fraction contains a mixture of hydrocarbons.

C Gaseous fractions are formed by breaking covalent bonds.

D The fractionating column is hottest at the top.

(Total 1 mark)

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 Octane and isooctane are structural isomers with the molecular formula C8H18.
5. The displayed formulas and boiling points of octane and isooctane are shown in Figure 1.

Figure 1

(a) Give the IUPAC name for isooctane.

___________________________________________________________________
(1)

(b) Octane and isooctane can be separated in the laboratory.

Name a laboratory technique that could be used to separate isooctane from a mixture of
octane and isooctane.

Outline how this technique separates isooctane from octane.

Name _____________________________________________________________

Outline ____________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Isooctane is added to petrol to increase its octane rating. Some high-performance
engines require fuel with a higher octane rating.

Write an equation for the complete combustion of isooctane. Use the molecular formula
(C8H18) of isooctane in your equation.

___________________________________________________________________
(1)

Rivers Academy West London Page 8 of 45

(d) Explain, in general terms, how a catalyst works.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(e) Carbon monoxide is produced when incomplete combustion takes place in engines.
Nitrogen monoxide is another pollutant produced in car engines.

Write an equation to show how these pollutants react together in a catalytic converter.

___________________________________________________________________
(1)

(f) Platinum, palladium and rhodium are metals used inside catalytic converters. A very
thin layer of the metals is used on a honeycomb ceramic support.

Explain why a thin layer is used in this way.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

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 (g) Oleic acid (C18H34O2) is a straight-chain fatty acid obtained from plant oils. Isooctane
can be made from oleic acid. The skeletal formula of oleic acid is shown in Figure 2.

Figure 2

Identify a reagent that could be used in a chemical test to show that oleic acid is
unsaturated.

State what would be observed in this test.

Reagent ___________________________________________________________

Observation _________________________________________________________

___________________________________________________________________
(2)
(Total 12 marks)

Central heating fuel, obtained by the fractional distillation of crude oil, contains saturated
6. hydrocarbons with the molecular formula C16H34

(a) Give the meaning of the terms saturated and hydrocarbon as applied to saturated
hydrocarbons.

Saturated __________________________________________________________

___________________________________________________________________

Hydrocarbon ________________________________________________________

___________________________________________________________________
(2)

(b) If the boiler for a central heating system is faulty, a poisonous gas may be produced during
the combustion of C16H34

Write an equation for the reaction that forms this poisonous gas and one other product only.

___________________________________________________________________
(1)

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(c) Explain why the sulfur compounds found in crude oil should be removed from the fractions
before they are used for central heating fuel.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(d) A hydrocarbon C16H34 can be cracked to form C8H18, ethene and propene.

(i) Write an equation to show this cracking reaction.

______________________________________________________________
(1)

(ii) Suggest one important substance manufactured on a large scale from propene.

______________________________________________________________
(1)

(iii) Draw the displayed formula of the functional group isomer of propene.

(1)

Rivers Academy West London Page 11 of 45

 (e) There are many structural isomers with the molecular formula C8H18

Draw the structure of 2,3,3-trimethylpentane.

(1)

(f) A compound C8H18 reacts with chlorine to give several haloalkanes.

Give the IUPAC name of the following haloalkane.

___________________________________________________________________
(1)
(Total 10 marks)

Some oil-fired heaters use paraffin as a fuel.

7. 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)

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(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)

(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)

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 (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)

(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)

The following table shows the boiling points of some straight-chain alkanes.
8.
CH4 C 2H 6 C 3H 8 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)

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(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 C4H10

___________________________________________________________________
(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)

(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)

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 (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.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

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 (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)

Pent-1-ene is a member of the alkene homologous series.

9.
(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)
Rivers Academy West London Page 17 of 45
 (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)

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 Petrol contains saturated hydrocarbons. Some of the molecules in petrol have the molecular
10. formula C8H18 and are referred to as octanes. These octanes can be obtained from crude oil by
fractional distillation and by cracking suitable heavier fractions.

Petrol burns completely in a plentiful supply of air but can undergo incomplete combustion in a
car engine.

(a) State the meaning of both the words saturated and hydrocarbon as applied to the term
saturated hydrocarbon.

Name the homologous series to which C8H18 belongs.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(b) Outline the essential features of the fractional distillation of crude oil that enable the crude
oil to be separated into fractions.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(4)

Rivers Academy West London Page 19 of 45

(c) C8H18 is obtained by the catalytic cracking of suitable heavy fractions.
State what is meant by the term cracking and name the catalyst used in catalytic cracking.

Write an equation to show how one molecule of C14H30 is cracked to form one molecule of
C8H18 and one molecule of another hydrocarbon.

Explain why oil companies need to crack ‘suitable heavy fractions’.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(4)

(d) Write an equation for the incomplete combustion of C8H18 to form carbon monoxide and
water only.

A catalytic converter is used to remove carbon monoxide from the exhaust gases in a car.
Identify a catalyst used in the catalytic converter.

Write an equation to show how carbon monoxide is removed in a catalytic converter.

State why the water produced in the exhaust gases may contribute to global warming.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(4)

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(e) When some petrol was accidentally contaminated in 2007, the sensors in the affected cars
caused a decrease in the supply of petrol to the engine.

Suggest the effect that the contaminated fuel would have on the performance of the cars.

State how the oil company might have recognised the problem before the petrol was sold.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(f) The molecular formula C8H18 represents several structural isomers.

State what is meant by the term structural isomers.

Name the following structural isomer of C8H18

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)
(Total 20 marks)

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 The fractions obtained from petroleum contain saturated hydrocarbons that belong to the
11. homologous series of alkanes.

(a) Any homologous series can be represented by a general formula.

(i) State two other characteristics of homologous series.

Characteristic 1 _________________________________________________

______________________________________________________________

Characteristic 2 _________________________________________________

______________________________________________________________

(ii) Name the process which is used to obtain the fractions from petroleum.

______________________________________________________________

(iii) State what is meant by the term saturated, as applied to hydrocarbons.

______________________________________________________________

______________________________________________________________
(4)

(b) Decane has the molecular formula C10H22

(i) State what is meant by the term molecular formula.

______________________________________________________________

______________________________________________________________

(ii) Give the molecular formula of the alkane which contains 14 carbon atoms.

______________________________________________________________

(iii) Write an equation for the incomplete combustion of decane, C10H22, to produce
carbon and water only.

______________________________________________________________
(3)

(c) When petrol is burned in an internal combustion engine, some nitrogen monoxide, NO,
is formed. This pollutant is removed from the exhaust gases by means of a reaction in a
catalytic converter.

(i) Write an equation for the reaction between nitrogen and oxygen to form nitrogen
monoxide.

______________________________________________________________

Rivers Academy West London Page 22 of 45

 (ii) Identify a catalyst used in a catalytic converter.

______________________________________________________________

(iii) Write an equation to show how nitrogen monoxide is removed from the exhaust
gases as they pass through a catalytic converter.

______________________________________________________________
(3)
(Total 10 marks)

(a) (i) Name the process used to separate petroleum into fractions.
12.
______________________________________________________________

(ii) Give the molecular formula for an alkane with nine carbon atoms.

______________________________________________________________

______________________________________________________________

(iii) Write an equation for the complete combustion of the alkane C11H24

______________________________________________________________

(iv) Write an equation for the incomplete combustion of C11H24 to produce carbon
and water only.

______________________________________________________________
(4)

(b) Alkenes can be produced by cracking the naphtha fraction obtained from petroleum.

(i) Write an equation for the thermal cracking of one molecule of C10 H22 to give
one molecule of propene and one molecule of an alkane only.

______________________________________________________________

(ii) Draw the structure of the chain isomer of but-1-ene.

(2)

Rivers Academy West London Page 23 of 45

 (c) The alkanes and the alkenes are examples of homologous series of compounds.
One feature of an homologous series is the gradual change in physical properties
as the relative molecular mass increases. State two other general features of an
homologous series of compounds.

Feature 1 ___________________________________________________________

___________________________________________________________________

Feature 2 ___________________________________________________________

___________________________________________________________________
(2)
(Total 8 marks)

(a) Crude oil is separated into fractions by fractional distillation. Outline how different fractions
13. are obtained by this process.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

Rivers Academy West London Page 24 of 45

(b) The table below gives details of the supply of, and demand for, some crude oil fractions.

Approximate %
Fractions
Typical supply Global
from crude oil demand

Gases 2 4

Petrol and naphtha 16 27

Kerosine 13 8

Gas oil 19 23

Fuel oil and bitumen 50 38

(i) Use the data given above to explain why catalytic cracking of crude oil fractions is
commercially important.

______________________________________________________________

______________________________________________________________

______________________________________________________________

(ii) Give the two main types of product obtained by catalytic cracking.

Type 1 ________________________________________________________

Type 2 ________________________________________________________
(4)

(c) Name a catalyst used in catalytic cracking. State the type of mechanism involved and
outline the industrial conditions used in the process.

Catalyst ____________________________________________________________

Conditions __________________________________________________________
(4)
(Total 11 marks)

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 (a) Gas oil (diesel), kerosine (paraffin), mineral oil (lubricating oil) and petrol (gasoline) are four
14. of the five fractions obtained by the fractional distillation of crude oil within the temperature
range 40–400 °C.

Identify the missing fraction and state the order in which the five fractions are removed as
the fractionating column is ascended. Give two reasons why the fractions collect at
different levels in the fractionating column.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(4)

(b) Thermal cracking of large hydrocarbon molecules is used to produce alkenes. State the
type of mechanism involved in this process. Write an equation for the thermal cracking of
C21H44 in which ethene and propene are produced in a 3:2 molar ratio together with one
other product.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

Rivers Academy West London Page 26 of 45

(c) Write equations, where appropriate, to illustrate your answers to the questions below.

(i) Explain why it is desirable that none of the sulphur-containing impurities naturally
found in crude oil are present in petroleum fractions.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(ii) The pollutant gas NO is found in the exhaust gases from petrol engines. Explain why
NO is formed in petrol engines but is not readily formed when petrol burns in the
open air.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(3)

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(iii) The pollutant gas CO is also found in the exhaust gases from petrol engines. Explain
how CO and NO are removed from the exhaust gases and why the removal of each
of them is desirable.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(5)
(Total 17 marks)

Rivers Academy West London Page 28 of 45

Mark schemes
D
1.
Kerosene is a mixture of compounds
[1]

(a) Step 1
2.
M1 fractional distillation
1

M2 separated into mixtures of compounds with similar boiling points / similar

sized molecules
M2 to separate naphtha from other compounds; to separate
compounds by chain length / size / boiling point
1

Step 2

M3 (thermal) cracking
M3 not catalytic cracking
1

M4 to make alkenes / propene / shorter molecules

1

Step 3

M5 (addition) polymerisation
M5 not condensation polymerisation 1
1

M6 molecules joined together or to produce long chain molecule

For each step the two marks are independent
1

(b) no polar bonds (in chain) / non-polar

Do not allow if only C-H bonds mentioned as non polar
1

(c) to prevent build-up of waste (in landfill) OR they can be broken down by natural
processes
1
[8]

(a) A group of (hydrocarbons/compounds) with similar boiling points

3.
Allow compounds that boil in a similar range of temperatures
Compounds with similar (carbon) chain length with C5-C12 range or
within range
1

Rivers Academy West London Page 29 of 45

(b) zeolite
Allow Aluminosilicate or aluminium oxide
M1

All formulae correct

M2

Balanced equation C16H34 → C6H14 + 2 C5H10

M3

(c) C=O bonds vibrate at the same frequency as IR

The difference in energy between the ground and first excited
vibrational state of CO2 is equal to the energy of the infrared
radiation.

Allow
Bond vibrations match frequency of IR radiation
C=O bonds vibrate in range 1680-1750cm-1
C=O bonds are polar
1

(d)

Curly arrow from N lp to H

Curly arrow from N-H bond to N+
M1
M2

2-aminoethanol
Allow 2-hydroxyethylamine 2-hydroxyethanamine ethanolamine
M3

Base
Allow proton acceptor / removes H+ / electron pair donor M1
M4

Rivers Academy West London Page 30 of 45

(e)

Allow these shapes with lines instead of wedges and dashed lines
M1

M2

Smaller
Allow comparison of correct numbers
M3

lone (or non-bonding) pair repulsion greater than bond pair repulsion
M4

(f)

This question is marked using Levels of Response. Refer to the Mark Scheme
Instructions for Examiners for guidance.

All stages are covered and each stage is generally correct and
Level 3 virtually complete.

5-6 Answer is communicated coherently and shows a logical

marks progression from Stage 1 to Stages 2 and 3
Covers at least 2 points for stage 1, 2 for stage 2 and 3 for stage 3.

All stages are covered but stage(s) may be incomplete or may

contain inaccuracies OR two stages are covered and are generally
Level 2 correct and virtually complete.
3-4 Answer is communicated mainly coherently and shows a logical
marks progression from Stage 1 to Stages 2 and 3.
Covers at least 1 point for stage 1 to stages 2 and 3.

Two stages are covered but stage(s) may be incomplete or may

Level 1 contain inaccuracies OR only one stage is covered but is generally
correct and virtually complete.
1-2
marks Answer includes isolated statements but these are not presented in
a logical order.

Level 0 Insufficient correct chemistry to gain a mark

Rivers Academy West London Page 31 of 45

 Indicative Chemistry content

Stage 1 names of processes

1a Photosynthesis (is the natural process in plants that takes CO2 from the air)

1b Fermentation (is the process used to make bioethanol releasing some CO2)

1c Combustion (is the process where bioethanol is burned and releases CO2)

Stage 2 Equations

2a 6CO2 + 6H2O → C6H12O6 + 6O2

2b C6H12O6 → 2C2H5OH + 2CO2

2c 2C2H5OH + 6O2 → 6H2O + 4CO2

Stage 3 Carbon neutrality and environmental issues

3a Deforestation / Sacrifice land that could be used for food

3b Loss of biodiversity / habitat

3c 6CO2 in and 6CO2 out but it isn't actually C neutral as fuel is used in
production, distribution, etc
6
[19]

B
4.
[1]

(a) 2,2,4-trimethylpentane
5.
This answer only but ignore punctuation
1

Rivers Academy West London Page 32 of 45

(b) M1 (fractional or simple) distillation
Incorrect process in M1 CE=0
If M1 blank, mark on for M2 and M3 (ignore boiling, condensing)
1

M2 idea that isooctane / the one with the lower boiling point boils (first)
(or reaches top of column first)
Ignore reference to octane boiling and being collected at higher
temperature
If temperature referred to, should be between 99 and 124°C
“it” refers to isooctane
M2 – allow vaporises/evaporates first
1

M3 idea that isooctane condenses / liquefies and collected

Penalise M2 and M3 if octane boils first
In M2 and M3 – if no specific reference to individual alkanes, could
score one mark for M2 + M3 combined if M2 and M3 both otherwise
correct
M2 and M3 must refer to a laboratory apparatus (not to an industrial
process)
1

(c) C8H18 + 12½O2 → 8CO2 + 9H2O

Accept multiples; ignore state symbols
Accept any correct structural representation of isooctane
1

(d) M1 Alternative route/mechanism/pathway

1

M2 With lower activation energy

Accept Ea for activation energy
1

(e) 2CO + 2NO → 2CO2 + N2

Accept multiples; ignore state symbols
1

(f) M1 to reduce amount of metals needed / small amount of metal needed

Relates to low amount of metal
1

M2 Increase / maximise / produce large surface area or to give catalyst a

larger surface area: volume ratio or so that high(er) proportion of
atoms/metal is on surface
Is related to large surface area
1

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 (g) M1 bromine (water or in organic solvent or CCl4) / Br2 (aq) / Br2
No reagent or an incorrect reagent (e.g. bromide), CE=0;
Penalise Br (or incorrect formula of other correct reagent) but mark
on for M2
It must be a whole reagent and/or correct formula
If oxidation state given in name, it must be correct
If ‘manganate’ or ‘manganate(IV)’ or incorrect formula, penalise M1
but mark on
Ignore ‘acidified’
1

M2 (orange/yellow to) colourless / decolourised / loses its colour

Ignore goes clear
Ignore brown/red, but penalise other incorrect colours
1
Alternatives:
M1 = potassium manganate(VII), M2 = colourless
M1 = conc sulfuric acid, M2 = brown
M1 = iodine, M2 = colourless
[12]

(a) Saturated − single bonds only / no double bonds

6. 1

Hydrocarbon − contains carbon and hydrogen (atoms) only

1

(b) C16H34 + 16.5O2 16CO + 17H2O

Allow multiples
1

(c) (On combustion) SO2 produced

Allow equation to produce SO2. Ignore sulfur oxides.
1

Which causes acid rain

If formula shown it must be correct
M2 is dependent on M1. But if M1 is sulfur oxides, allow M2.
For M2 allow consequence of acid rain or SO2.
Ignore greenhouse effect and toxic
1

(d) (i) C16H34 C8H18 + C2H4 + 2C3H6

Allow multiples
1

Rivers Academy West London Page 34 of 45

 (ii) polypropene / propan(-1 or 2-)ol / propane(-1,2-)diol / isopropanol / propanone /
propanal
Accept alternative names
Ignore plastic and polymer
1

(iii)

(e)

Allow any unambiguous representation

1

(f) 2,4-dichloro-2,4-dimethylhexane
Only but ignore punctuation
1
[10]

(a) Crude oil OR petroleum

7.
Not petrol.
1

Fractional distillation / fractionation

Not distillation alone.
1

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

Allow balanced equations that produce CO2 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

Rivers Academy West London Page 35 of 45

 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
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

C 3H 7
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

Rivers Academy West London Page 36 of 45

 (f) Cl2
Only.

Cl–Cl
Not CL2 or Cl2 or CL2 or Cl2 or CL2.
Ignore Chlorine.
1
[16]

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

8. 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

Rivers Academy West London Page 37 of 45

 (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

(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]

Rivers Academy West London Page 38 of 45

 (a) (Different) boiling points
9.
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

Rivers Academy West London Page 39 of 45

 (iii)

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]

Rivers Academy West London Page 40 of 45

 (a) Single bonds only /no double or multiple bonds;
10. 1

Contains carbon and hydrogen only;

C and H only
not C and H molecules
1

Alkanes;
1

(b) (1) Fractions or hydrocarbons or compounds have different

boiling points/ separation depends on bp;
Ignore mp and vdw
1

(2) bp depends on size/ Mr/ chain length;

If refer to bond breaking/cracking/ blast furnace/oxygen/air 2 max
1

(3) Temp gradient in tower or column / cooler at top of column

or vice versa;
QWC
1

(4) Higher bp / larger or heavier molecules at bottom (of

column) or vice versa;
Not increasing size of fraction
Not gases at top
1

(c) Large molecules or compounds or long chain hydrocarbons

(broken) into smaller molecules or compounds or smaller
chain hydrocarbons;
QWC
1

Zeolite or aluminosilicate (catalyst);

1

C14H30 → C8H18 + C6H12;

Only
1

Smaller chain molecules are in more demand or have higher

value or vice versa;
Insufficient to say more useful/have more uses
1

Rivers Academy West London Page 41 of 45

 (d) C8H18 + 8½ O2 → 8CO + 9H2O;
Allow multiples
1

Rh/ Pd/Pt/lr or in words;

Penalise contradiction of name and symbol
1

2CO + 2NO → 2CO2 + N2 / 2CO + O2 → 2CO2;

Allow multiples
1

Greenhouse gas/ absorbs infrared radiation;

1

(e) car less powerful/ car stops/ reduced performance/ won’t run
smoothly/ can’t accelerate;
Not incomplete combustion or bad effect on engine
Not doesn’t go as far.
1

Test it (before sale) /Quality control etc;

1

(f) (compounds with) same molecular formula / same no and type of atoms;
Not atoms/elements with same molecular formula.
If same chemical formula, can allow M2
1

And different structure/ structural formula;

M2 consequential on M1
Allow displayed formula for M2
1

2,2,4-trimethylpentane;
Only (but allow numbers in any order)
1
[20]

(a) (i) any two from:

11. 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
(penalise ‘same molecular formula’)
(penalise ‘same empirical formula’)
2

(ii) fractional distillation or fractionation

1

Rivers Academy West London Page 42 of 45

 (iii) contains only single bonds or has no double bonds
(credit ‘every carbon is bonded to four other atoms’ provided it does
not contradict by suggesting that this will always be H)
1

(b) (i) the molecular formula gives the actual number of atoms of each
element/type in a molecule/hydrocarbon/compound/formula
(penalise ‘amount of atoms’)
(penalise ‘ratio of atoms’)
1

(ii) C14H30 only

(penalise as a contradiction if correct answer is
accompanied by other structural formulae)
1

(iii) C10H22 + 5½O2 → 10C + 11H2O

(or double this equation)
1

(c) (i) ½N2 + ½O2 → NO

(or double this equation)
1

(ii) Platinum or palladium or rhodium

1

(iii) 2CO + 2NO → 2CO2 + N2 or

2NO → N2 + O2 or
(ignore extra O2 molecules provided the equation balances)

C + 2NO → CO2 + N2
(or half of each of these equations)

C8H18 + 25NO → 8CO2 + 12½N2 + 9H2O

(or double this equation)
1
[10]

(a) (i) fractional distillation or fractionation

12. 1

(ii) C9H20 only

1

(iii) C11H24 + 17O2 → 11CO2 + 12H2O

1

(iv) C11H24 + 6O2 → 11C + 12H2O

1

Rivers Academy West London Page 43 of 45

 (b) (i) C10H22 → C3H6 + C7H16
1

(ii) correctly drawn structure of methylpropene

(insist on clearly drawn C-C and C=C bonds)
1

(c) Any two from

o chemically similar or chemically the same or react in

the same way

o same functional group

o same general formula

o differ by CH2
(penalise same molecular formula or same empirical formula)
2
[8]

(a) Crude oil is heated to vaporise it / oil vaporised (1)

13. (Vapour passed into fractionating) tower / column (1)
Top of tower cooler than bottom
or negative temperature gradient (1)
fractions separated by b.p
OR condensed at different temperatures OR levels
OR low boiling fractions at the top
OR at the top small molecules or light components (1)
max 3

(b) (i) Identify shortfall in supply - e.g. petrol / small molecules (1)
Higher value products OR more useful products (1)
OR cracking produces more of material (problem solving)

(ii) Motor fuels

Aromatic hydrocarbons
Branched alkanes / hydrocarbons
Cycloalkanes
Any two (2)
Ignore specific fractions, alkanes, shorter alkanes, penalise
alkenes, and hydrogen
4

(c) Catalyst: Zeolite / aluminosilicate (1)

Type of mechanism: Carbocation / heterolytic fission (1)
Conditions: High temp OR around 450 °C [300 – 600] °C NOT heat / warm (1)
Slight pressure [> 1 atm 10 atm OR 1 megaPa, 1000 kPa] (1)
NOT high pressure
4
[11]

Rivers Academy West London Page 44 of 45

 (a) Missing fraction = naphtha (allow naphtha from list if not quoted
14. separately) (1) Order = mineral oil (lubricating oil), gas oil (diesel),

kerosene (paraffin),
naphtha, petrol (gasoline) (1)
Mark order consequential on M1 (if no missing fraction
given, M2 = 0) Accept correct reversed order

Negative temperature gradient on the column

or temperature of column decreases upwards (1)

Larger molecules or heavier fractions condense at higher

temperatures or lower down the column or reference to
different boiling points
(ignore mp) (1)
4

(b) Type of mechanism = (free) radical / homolytic

fission - used in complete sentence/phrase (1)

C21H44 → 3 C2H4 + 2 C3H6 + C9H20 correct alkenes (1)

Accept CH2CH2 & CH2CHCH3 all correct (1)
3

(c) (i) Sulphur (containing impurities) burn to form or forms SO2 or

oxides of sulphur (if oxide identified, must be correct) (1)
OR equation: e.g. S + O2 → SO2 or H2S + 1½O2 → SO2 + H2O

Leading to acid rain (must have specified oxides of S or burning)

or toxic product or respiratory problems (1)

(ii) NO formed by reaction between N2 and O2 from the air (1)

OR N2 +O2 → 2NO
High combustion temperature or spark in engine (1)
provides EA or sufficient heat / energy to break N N (1)

(iii) Need to remove NO as forms acid rain or toxic product or causes

respiratory problems (1)
2NO + O2 → 2NO2 (1)
4NO2 + O2 + 2H2O → 4HNO3 (1)

Need to remove CO as it is poisonous (1)

Catalytic converter (1)

uses Pt / Rh / Pd / Ir (wrong answer cancels a correct one) (1)
Provides active sites / reduces EA (1)
Forms N2 + CO2 (1)
2NO + 2CO → N2 + 2CO2 (correct equation worth last 2 marks) (1)
Max 10
[17]

Rivers Academy West London Page 45 of 45