CIE Jun 2014 v2 Paper 4 Q5

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12 Although now remembered for his music, the Russian composer Alexander Borodin was a chemist. He is credited with the discovery of the aldol reaction, a product of which is compound J. J shows the following properties: PMTits molecular formula is C4H8O2, it is neutral, it reacts with sodium metal, it reacts with Fehling's solution, it does not react with aqueous bromine. (a) Suggest which functional groups are responsible for the reactions with (i) sodium,(ii) Fehling's solution.[2] (b) The result of the bromine test shows a functional group is absent from compound J. Suggest the identity of this functional group.[1] (c) In the boxes below, draw three possible straight-chain structures for J thatt the above results, and that are structural isomers of each other. [3]UCLES 2014 9701/42/M/J/14<br /> PMT 13 (d) Compound J reacts with alkaline aqueous iodine to give a pale yellow precipitate. (i) Which functional group does this reaction show that J contains?(ii) Which of your three structures K, L or M contains this group and is therefore J?[2] (e) Compound J exists as stereoisomers. (i) Name the type of stereoisomerism shown by J.(ii) Draw two structures of J to illustrate this stereoisomerism. [2] [Total: 10]UCLES 2014 9701/42/M/J/14 [Turn over<br />

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