Syllabus Edition
First teaching 2020
Last exams 2024
Benzene undergoes substitution reactions. State the equation for the reaction of benzene with nitric acid to produce nitrobenzene and water.
The structure of methylbenzene is shown below in Fig. 1.1.
Draw the structures of the two isomers of choromethylbenzene formed from the reaction of methyl benzene and Cl2 in the presence of AlCl3.
State the type of reaction that benzene will typically undergo.
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This question is about the bromination of benzene.
State the name of the mechanism that benzene will undergo if reacted with bromine in the presence of a halogen carrier to form bromobenzene, C6H5Br.
Write an equation to show how the halogen carrier generates the Br+ ion in order to allow the reaction in part (a) to occur.
Complete the mechanism in Fig. 2.1 for the formation of bromobenzene. Include relevant charges where appropriate.
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This question is about the reactions of methylbenzene.
Draw the structure of compound A in Fig. 3.1.
Draw the structure of compound B in Fig. 3.2.
State the reagents and conditions required for reaction 1 in Fig. 3.3 for the formation of benzoic acid from methylbenzene.
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The nitration of benzene is the first important step in manufacturing dyes and explosives.
Compound B is produced in two steps as outlined in Fig. 1.1.
Fig. 1.1
Draw the dot-and-cross diagram for the structure of the catalyst, once the electrophile has been generated in part (b).
Explain why benzene can generally only undergo substitution reactions.
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Fig. 2.1 shows the formation of a ketone followed by an alcohol.
Fig. 2.1
Draw the mechanism to show the formation of the catalyst responsible for step 1.
Draw the mechanism for the formation of the ketone, including the regeneration of the catalyst required.
State the reagents required for step 2.
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Benzene can be converted into cyclohexane as shown in Fig. 3.1.
Fig. 3.1
When benzene reacts with SO3, as shown in Fig. 3.2, benzenesulfonic acid is produced.
Fig. 3.2
The mechanism of this reaction is similar to that of the nitration of benzene. Concentrated H2SO4 is used in an initial step to generate the SO3H+ electrophile as shown.
SO3 + H2SO4 → SO3H+ + HSO4–
3-aminobenzoic acid can be synthesised from methylbenzene in three steps as shown in Fig. 3.4.
Fig. 3.4
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