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Q1. (a) Chloromethane can be made by the reaction of chlorine with methane.

(i) Give one essential condition for this reaction.

.............................................................................................................

(ii) Name the mechanism for this reaction.

.............................................................................................................

(iii) Further substitution can occur during this reaction. Identify the main organic
product when a large excess of chlorine is used in this reaction.

.............................................................................................................
(3)

(b) Ethanenitrile can be made by reacting chloromethane with potassium cyanide.

(i) Write an equation for this reaction.

.............................................................................................................

(ii) Name the mechanism for this reaction.

.............................................................................................................

(iii) Explain, in terms of bond enthalpies, why bromomethane reacts faster than
chloromethane with potassium cyanide.

.............................................................................................................

.............................................................................................................

.............................................................................................................
(3)

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 (c) Ethanenitrile can be hydrolysed to a carboxylic acid by heating it under reflux with a
dilute acid. Identify the carboxylic acid formed in this reaction.

......................................................................................................................
(1)

(d) Chloromethane can react with ammonia to produce a primary amine.

(i) What feature of the chloromethane molecule makes it susceptible to attack by

.............................................................................................................

(ii) Name the amine produced in this reaction.

.............................................................................................................

(iii) Outline a mechanism for this reaction.

(6)
(Total 13 marks)

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Q2. Ethene is an important starting point for the manufacture of plastics and
pharmaceutical chemicals. Most of the ethene used by industry is produced by the
thermal cracking of ethane obtained from North Sea gas (Reaction 1). It is also possible
to make ethene either from chloroethane (Reaction 2) or from ethanol (Reaction 3).

(a) Give essential conditions and reagents for each of Reactions 2 and 3.
(4)

(b) Name and outline a mechanism for Reaction 2. Suggest a reason why
chloroethane is not chosen by industry as a starting material to make ethene
commercially.
(5)

(c) Name and outline a mechanism for Reaction 3. Suggest why this route to ethene
may become used more commonly in the future as supplies of North Sea gas begin
to run out.
(6)
(Total 15 marks)

Q3. (a) Propene reacts with hydrogen bromide by an electrophilic addition mechanism
forming 2-bromopropane as the major product.

The equation for this reaction is shown below.

(i) Outline the mechanism for this reaction, showing the structure of the
intermediate carbocation formed.

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 (ii) Give the structure of the alternative carbocation which could be formed in the
reaction between propene and hydrogen bromide.

(5)

(b) A substitution reaction occurs when 2-bromopropane reacts with aqueous sodium
hydroxide.

(i) Draw the structure of the organic product of this reaction and give its name.

Structure

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 Name ..................................................................................................

(ii) Name and outline the mechanism for this reaction.

Name of mechanism ...........................................................................

Mechanism

(5)

(c) Under different conditions, 2-bromopropane reacts with sodium hydroxide to

(i) Name the mechanism for this reaction.

.............................................................................................................

(ii) State the role of sodium hydroxide in this reaction.

.............................................................................................................
(2)
(Total 12 marks)

Q4. (a) Compounds with double bonds between carbon atoms can exhibit geometrical

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 isomerism.

(i) Draw structures for the two geometrical isomers of 1,2-dichloroethene.

Isomer 1 Isomer 2

(ii) What feature of the double bond prevents isomer 1 from changing into isomer
2?

.............................................................................................................
(3)

(b) When 2-chloropropane reacts with sodium hydroxide, two different reactions occur.
Each reaction produces a different organic product.

(i) Outline a mechanism for Reaction 1 and state the role of the hydroxide ion in
this reaction.

Mechanism

Role of the hydroxide ion ....................................................................

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 (ii) Outline a mechanism for Reaction 2 and state the role of the hydroxide ion in
this reaction.

Mechanism

Role of the hydroxide ion ....................................................................

Q5. When chlorine reacts with trichloromethane, tetrachloromethane, CCl4, is formed.

(a) (i) Write the overall equation for this reaction.

.............................................................................................................

(ii) State one essential condition for this reaction.

.............................................................................................................
(2)

(b) The mechanism for the chlorination of trichloromethane is free-radical substitution,

Initiation step

......................................................................................................................

First propagation step

......................................................................................................................

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 Second propagation step

......................................................................................................................

A termination step

......................................................................................................................
(4)
(Total 6 marks)

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