(i)   A compound D has the molecular formula C2H4O2 and is obtained
      from a reaction between methanoic acid and methanol. Write an
      equation for this reaction and state the name of D.
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(ii)    A second compound, E, has the same molecular formula as D and
       has acidic properties.
       State the name of compound E.
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    …………………………………………………………………………………………..
Ans: (i)    CH3OH + HCOOH ----> HCOOCH3 + H2O   
              for both reactants and [1] for both products
              (accept C2H4O2) methyl methanoate;
       (ii)    ethanoic acid;   

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A student prepared a sample of compound Y from benzene as follows:
    C6H6 → C6H5CH2CH3 → C6H5CHClCH3
                           X                        Y
(a)    (i)    The first step was the conversion of benzene to compound X,
               using chloroethane as the reagent and aluminium chloride as
               a catalyst.Write the equation for the reaction and give equations
               for the mechanism.
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              ............................................................................................................................


        (ii)    Name the type of mechanism that occurs in the second step when
               X is converted to Y.
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(b)    (i)    Draw two structures for compound Y, showing the relationship
               between them.

       (ii)    Explain the term plane-polarized light and describe how the optical
              isomers of Y could be distinguished using a polarimeter.
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      (iii)    Explain why the sample of Y produced by the student did not show
              optical activity.
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(c)    Samples of compound Y and chlorobenzene are warmed separately with
        aqueous sodium hydroxide. State, with a reason, whether compound Y
        or chlorobenzene would react more slowly.
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            ......................................................................................................................................
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(Total 16 marks)

Ans : (a)    (i)    C6H6 + CH3CH2Cl ---> C6H5CH2CH3 + HCl;
                        CH3CH2Cl + AlCl3 ---> CH3CH2+ + AlCl4–;  
                        [1] for arrow
                (ii)    free radical substitution;    1
        (b)    (i)    one correct structure;
                       second structure clearly a mirror image;
                (ii)    light in which all waves/vibrations are in one plane;
                        plane-polarized light passed through each isomer (solution);
                        plane of polarization rotates;
                        in opposite directions for each isomer;    4
                (iii)    equal amounts of each isomer were formed/racemic mixture formed;
                        optical activities/rotations cancelled out;    2
        (c)    chlorobenzene;
                nucleophile/OH– repelled by delocalized electrons/carbon atom being
                attacked is less electron-deficient/carbon-chlorine bond is stronger;    2