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    Tutorial 13 Arenes

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    This document provides a tutorial on arenas (aromatic compounds) for H2 Chemistry students at Raffles Institution Junior College. It includes self-check questions to identify structural formulas of substituted benzene derivatives and suggest reactions. Discussion questions explore the synthesis of saccharin, nitration of methylbenzene, identification of compounds from reactivity data, transformations of methylbenzene, and the expected products of substitution reactions involving phenylamine and benzene. A challenging question examines an unexpected product from the reaction of phenylamine and explains the mechanism of benzene reacting with 1-bromopropane.

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    Tutorial 13 Arenes

    Uploaded by

    Dom
    361 views2 pages
    This document provides a tutorial on arenas (aromatic compounds) for H2 Chemistry students at Raffles Institution Junior College. It includes self-check questions to identify structural formulas of substituted benzene derivatives and suggest reactions. Discussion questions explore the synthesis of saccharin, nitration of methylbenzene, identification of compounds from reactivity data, transformations of methylbenzene, and the expected products of substitution reactions involving phenylamine and benzene. A challenging question examines an unexpected product from the reaction of phenylamine and explains the mechanism of benzene reacting with 1-bromopropane.

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    A level Chemistry

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    This document provides a tutorial on arenas (aromatic compounds) for H2 Chemistry students at Raffles Institution Junior College. It includes self-check questions to identify structural formulas of substituted benzene derivatives and suggest reactions. Discussion questions explore the synthesis of saccharin, nitration of methylbenzene, identification of compounds from reactivity data, transformations of methylbenzene, and the expected products of substitution reactions involving phenylamine and benzene. A challenging question examines an unexpected product from the reaction of phenylamine and explains the mechanism of benzene reacting with 1-bromopropane.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    361 views2 pages

    Tutorial 13 Arenes

    Uploaded by

    Dom
    This document provides a tutorial on arenas (aromatic compounds) for H2 Chemistry students at Raffles Institution Junior College. It includes self-check questions to identify structural formulas of substituted benzene derivatives and suggest reactions. Discussion questions explore the synthesis of saccharin, nitration of methylbenzene, identification of compounds from reactivity data, transformations of methylbenzene, and the expected products of substitution reactions involving phenylamine and benzene. A challenging question examines an unexpected product from the reaction of phenylamine and explains the mechanism of benzene reacting with 1-bromopropane.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 2

    Raffles Institution (Junior College)

    H2 Chemistry 2010/11
    Tutorial 13 Arenes
    Prepared by: Mr Tham Zi Sheng

    REMINDER: Please study before you attempt the questions.


    Self-Check Questions
    1

    Give the structural formula of each compound given below.


    (i) 1-iodo-3-nitrobenzene
    (ii) 3-amino-5-hydroxybenzaldehyde
    (iii) 1,3-dichloro-2,5-diethylbenzene

    Suggest suitable reagents and conditions to carry out the conversions given below.
    (i) benzene
    1-chloro-2-ethylbenzene
    (ii) phenol
    2-hydroxybenzene-1,5-dicarboxylic acid

    Describe two simple chemical tests which would enable you to distinguish between
    ethylbenzene, phenylethene and benzoic acid. State clearly how each compound behaves in
    each test and write balanced equations for the reactions involved.

    Discussion Questions
    1

    Modified from J90/III/9


    (a) Saccharin is an artificial sweetening agent used in some soft drinks and is manufactured
    from methylbenzene by the following series of reactions.
    ClSO3H
    I

    CH3

    CH3

    CH3

    SO2Cl

    SO2NH2

    S
    O

    III

    N
    H

    COOH

    II

    SO2NH2

    (i) What types of reaction do steps I, II and III illustrate?


    (ii) Suggest reagents for step II.
    (b) When methylbenzene is nitrated by a mixture of concentrated nitric acid and concentrated
    sulfuric acid, the product consists largely of two isomers of formula C7H7NO2.
    (i) Draw the structural formulae of the two isomers.
    (ii) Briefly outline the mechanism of this reaction.

    Compound A, which has molecular formula, C8H8, burns with a smoky flame. A instantly
    decolourises bromine dissolved in tetrachloromethane. When A is refluxed with acidified
    potassium manganate(VII), a white crystalline precipitate, B, with molecular formula, C7H6O2,
    is obtained. A also undergoes hydrogenation in the presence of a platinum catalyst to form
    compound C, with molecular formula, C8H10. C has no apparent reaction with bromine in the
    dark. However, dense white fumes, D, appear if a small amount of iron powder is added.
    Identify the compounds A to D, giving their structural formulae, and explain your reasoning.

    Modified from N97/I/6


    Methylbenzene can be used an additive in unleaded petrol. Some chemical transformations of
    methylbenzene are given below.

    COOH

    I
    CH3

    II

    IV
    C7H5O2Br

    CH2Br

    III

    CH3
    Br
    A
    (a) Suggest reagents and conditions for each of the reactions I, II and III, and describe the
    type of reaction undergone in each case.
    (b) There are two other positional isomers of A. Draw their structural formulae, and suggest
    which one is more likely to be formed along with A in reaction III.
    (c) Reactions IV and V yield different isomers with the molecular formula, C7H6O2Br. Give the
    structural formulae of the isomers and explain why reactions IV and V produce different
    isomers.
    Challenging Question
    1

    (a) A student tried to synthesise 2-methylphenylamine by reacting phenylamine with


    chloromethane in the presence of aluminium chloride. However, the reaction yielded a
    different product, X.
    Suggest the structural formula of X and explain why the reaction yielded X instead of
    2-methylphenylamine.
    (b) When benzene reacts with 1-bromopropane in the presence of iron(III) bromide, the
    product formed is (methylethyl)benzene. Outline the mechanism of this reaction.

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