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4.2 Alkanes
Question Paper

Course OCR A Level Chemistry

Section 4. Core Organic Chemistry
Topic 4.2 Alkanes
Difficulty Hard

Time allowed: 70

Score: /58

Percentage: /100

Page 1 of 11

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Question 1a
This question is about combustion.
A diesel fuel containing the hydrocarbon tetradecane, C14H30, burns with a yellow flame.
Write a balanced symbol equation, including state symbols, for the reaction described.
[1 mark]

Question 1b
The majority of cars have an alkane fueled internal combustion engine as shown below.

Identify four pollutant products of combustion and describe how they are formed.
[4 marks]

Page 2 of 11

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Question 1c
Petrol vapour and air are compressed in a car engine. This can cause pre-ignition which can lead to an undesirable knocking
sound. Branched chain alkanes, such as 2,5-dimethylhexane, can be added to fuels as they are less likely to cause pre-
ignition and therefore improve fuel efficiency.
The boiling point of 2,5-dimethylhexane is 109.1 oC.
Explain the difference in boiling point between 2,5-dimethylhexane with its isomer 4-methylheptane.
[2 marks]

Question 1d
Explain why the production of carbon monoxide from a faulty heater in someone's home can have deadly consequences.
[5 marks]

Page 3 of 11

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Question 2a
Methane reacts with chlorine in the presence of UV light to form several products.
Two of these products are chloromethane and hydrogen chloride.
i)
Write an equation for the reaction between methane and chlorine to form chloromethane and hydrogen chloride.
[1]
ii)
Name one other chlorine-containing organic product which can be formed during this reaction.
[1]
[2 marks]

Question 2b
The mechanism for this reaction is free radical substitution.
Describe this mechanism for the free radical substitution of methane by chlorine.
Also suggest why a small amount of ethane is formed in the reaction.
[7 marks]

Page 4 of 11

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Question 2c
Explain the effect of increasing the intensity of UV light would have on the rate of reaction between methane and chlorine.
[3 marks]

Question 2d
Pentane is another saturated hydrocarbon which can undergo free radical substitution.
i)
Draw the 3D structure for pentane.
[1]
ii)
State and explain the bond angles between adjacent atoms in pentane.
[3]
[4 marks]

Page 5 of 11

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Question 2e
Pentane undergoes free radical substitution to form 3-chloropentane.
i)
Write two equations for the propagation steps involved in this mechanism.
[2]
ii)
Name an impurity that could be formed from the radicals in part i) that might be found in the final mixture.
[1]
iii)
Write an equation for the reaction between pentane and chlorine to form a disubstituted product.
[1]
[4 marks]

Page 6 of 11

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Question 3a
This question is about isomers of different alkanes.
Heptane can be produced by the fractional distillation of crude oil.
There are a total of eight branched isomers of heptane, four of which are shown below.

i)
Draw the skeletal formula for three other branched alkanes formed by heptane.
[3]
ii)
Give the IUPAC name of compound C.
[1]
[4 marks]

Page 7 of 11

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Question 3b
Explain which of the following isomers will have the highest boiling point.
2,3-dimethylpentane
3-methylhexane
2,4-dimethylpentane
[2 marks]

Question 3c
Octane and one of its isomers are shown below:

i)
Write an equation for the complete combustion of octane.

[1]
ii)
Give the IUPAC name for isooctane.
[1]
[2 marks]

Page 8 of 11

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Question 3d
The two isomers in part (c) can be separated in the lab.
Name and outline a technique that could be used to separate isooctane from a mixture of octane and isooctane.
[3 marks]

Question 3e
Describe the bonding and structure of octane.
Explain how its bonding and structure affects the following properties:
Reactivity
Boiling Point
[6 marks]

Page 9 of 11

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Question 4a
This question is about free radical substitution.
1,2-dibromoethane reacts with bromine in UV light to produce a mixture of further substituted haloalkanes.
i)
Write an equation for the initiation step.
[1]
ii)
Explain why this is an example of homolytic fission.
[1]
[2 marks]

Question 4b
Write two equations showing the propagation of this chain reaction to produce 1,1,2-tribromoethane.
[2 marks]

Question 4c
Traces of 1,2,3,4- tetrabromobutane are found in the reaction mixture.
i)
Write an equation to show how this product is formed.
[1]
ii)
Write a balanced symbol equation to show the overall reaction between 1,1,2-tribromoethane with bromine in UV light to form
hexabromoethane.
[1]
[2 marks]

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Question 4d
Using the information from this question and your own knowledge describe the limitations of free radical substitution.
[3 marks]

Page 11 of 11

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