CIE Jun 2014 v2 Paper 4 Q4

Answers available below

Both ethene and benzene react with bromine. 10 H2C CH2 Br2 room temperature BrCH2CH2Br PMT Al Br3 + heat Br2 Br HBr (a) What type of reaction is the reaction of bromine with (i) ethene,(ii) benzene?[1] (b) Write an equation to show the formation of the electrophile during the reaction between bromine and benzene.[1] (c) Each of these reactions involves an intermediate. (i) Draw the structure of the intermediate in each reaction. H2C CH2 Br2 Br2 (ii) Suggest why the product of the reaction between bromine and benzene, bromobenzene, is still unsaturated.[3]UCLES 2014 9701/42/M/J/14<br /> PMT 11 (d) When methylbenzene is nitrated, 4-nitromethylbenzene is formed, but when benzoic acid is nitrated, 3-nitrobenzoic acid is produced. Consider the following synthesis of 3-chlorobenzoic acid, F, from methylbenzene. Use the information given above to suggestthe structure of the intermediate E, the reagents and conditions needed for reactions 1 and 2. CH3 reaction 1 reaction 2 reagents and conditions for reaction 1 CO2H Clreagents and conditions for reaction 2[3] (e) Consider the following synthesis of 3-chlorophenylmethylamine, H, from F. Suggestthe structure of the intermediate G, the reagents for reactions 3 and 4. CO2H Cl reaction 3 NH3 reaction 4 CONH2 CH2NH2 Cl Cl reagents for reaction 3reagents for reaction 4[3]UCLES 2014 9701/42/M/J/14 [Total: 11] [Turn over<br />

Show answer