CIE Nov 2014 v2 Paper 2 Q3

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P, Q and R are structural isomers with the molecular formula C4H8. PMT All three compounds readily decolourise bromine in the dark. P and Q do not exhibit stereoisomerism but R exists as a pair of geometrical (cis-trans) isomers. All three compounds react with hot concentrated, acidi ed potassium manganate(VII) to produce a variety of products as shown in the table. compound products P Q R CO2 and S (C3H6O) CO2 and CH3CH2CO2H CH3CO2H only S reacts with 2,4-dinitrophenylhydrazine reagent, 2,4-DNPH, to form an orange crystalline product but does not react with Fehlings reagent. (a) Give the structural formulae of P, Q, R and S. PQRS[4] (b) (i) Explain what is meant by the term stereoisomerism.[2]UCLES 2014 9701/22/O/N/14<br />
 (ii) Draw the displayed formulae of the geometrical isomers of R and name them both. PMT namename[2] (c) State a reagent that could be used for the reduction of S and name the organic product of this reduction. reagentproduct[2] [Total: 10]UCLES 2014 9701/22/O/N/14 [Turn over<br />

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