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    Elizabeth Protoctis
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    This document provides a test on the chemistry of arenes with multiple questions. It begins with questions about the shape of benzene and reactions of benzene and cumene. Later questions cover substitution reactions of cumene, preparation of nitrobenzene derivatives, acid dissociation of sulfuric acid, properties of benzoic acid, synthesis of mefenamic acid from an amine, and conversion of benzene to cyclohexane. The test examines knowledge of arene structures, reaction mechanisms, acid-base chemistry and synthesis.

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    This document provides a test on the chemistry of arenes with multiple questions. It begins with questions about the shape of benzene and reactions of benzene and cumene. Later questions cover substitution reactions of cumene, preparation of nitrobenzene derivatives, acid dissociation of sulfuric acid, properties of benzoic acid, synthesis of mefenamic acid from an amine, and conversion of benzene to cyclohexane. The test examines knowledge of arene structures, reaction mechanisms, acid-base chemistry and synthesis.

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    24 views3 pages

    Test 4 - Chemistry of Arenes

    Uploaded by

    Elizabeth Protoctis
    This document provides a test on the chemistry of arenes with multiple questions. It begins with questions about the shape of benzene and reactions of benzene and cumene. Later questions cover substitution reactions of cumene, preparation of nitrobenzene derivatives, acid dissociation of sulfuric acid, properties of benzoic acid, synthesis of mefenamic acid from an amine, and conversion of benzene to cyclohexane. The test examines knowledge of arene structures, reaction mechanisms, acid-base chemistry and synthesis.

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    of 3

    14 February 2023

    Test 4- Chemistry of Arenes 35 Marks

    1 (a) By reference to the formation of σ and π bonds, describe and explain the shape of a benzene

    molecule, C6H6. [4]

    (b) Benzene reacts with D to give cumene and non-organic product E.

    (i) State the type of reaction mechanism that occurs in the reaction above. [1]

    (ii) Name the reactant D and the non-organic product E.

    E [2]

    (b) Cumene undergoes substitution reactions with chlorine to give several different isomeric

    products with the formula C9H11Cl. The substitution can occur in the aromatic ring or in the

    side-chain of cumene.

    (i) Describe the conditions that are used to ensure substitution takes place only in the

    aromatic ring. [1]

    (ii) Draw the structures of the two major isomeric products of the reaction, formula C 9H11Cl,

    when substitution takes place in the aromatic ring. [2]

    (iii) Describe the conditions that are used to ensure substitution takes place only in the

    side-chain. [1]

    (iv) Draw the structures of two isomeric products of the reaction, formula C 9H11Cl, when

    substitution takes place in the side-chain. [2]


    (c) Complete the following table to show the structures of the organic products formed when

    cumene reacts with each reagent.

    (d) 2,3-dimethylnitrobenzene can be prepared from 1,2-dimethylbenzene.

    (i) State the reagents and conditons for the reaction above. [2]

    (ii) Write an equation to show the electrophile for the reaction is generated. [1]

    (ii) Draw the mechanism of the reaction between this electrophile and 1,2-dimethylbenzene. Include
    all relevant curly arrows and charges. [4]

    (iii) When concentrated sulfuric acid is added to water, dissociation takes place in two stages.

    (i) Write the expression for the acid dissociation constant Ka 2. [1]

    (ii) H2SO4 is considered a strong acid whereas HSO 4– is considered a weak acid.

    Suggest how the magnitude of the acid dissociation constant for stage 1 compares to Ka2. [1]

    (e) Benzoic acid, C6H5CO2H, is a weak acid. A solution of 0.0250 mol dm –3 benzoic acid has a pH of
    2.90. Calculate the Ka of benzoic acid. [2]
    (e) The drug mefenamic acid can be made using 2,3-dimethylphenylamine in an excess of
    2-chlorobenzoic acid.

    (i) Deduce the molecular formula of mefenamic acid. [1]

    (ii) Name the functional groups, apart from the benzene ring, in mefenamic acid. [1]

    (iii) Calculate the maximum mass of mefenamic acid that could be formed from 5.00 g of

    2,3-dimethylphenylamine in this reaction. Give your answer to three significant figures. [3]

    (f) Benzene can be converted into cyclohexane.

    (i) For this reaction name the type of reaction and identify the reagent and conditions needed. [2]

    (ii) State the bond angles in benzene and cyclohexane.

    Explain your answers. [2]

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