CIE Nov 2014 v3 Paper 2 Q3

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P, Q, R and S are structural isomers with the molecular formula C5H10. PMT All four compounds readily decolourise bromine in the dark. P, R and S do not exhibit stereoisomerism but Q exists as a pair of geometrical (cis-trans) isomers. All four 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 S CO2 and CH3CH2CH2CO2H CH3CO2H and CH3CH2CO2H CO2 and T (C4H8O) CH3CO2H and (CH3)2CO T 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, S and T. PQRST[5] (b) (i) Explain what is meant by the term stereoisomerism.[2]UCLES 2014 9701/23/O/N/14<br /> (ii) Draw the displayed formulae of the geometrical isomers of Q and name them both. PMT namename[2] (c) Name the organic product of the reaction of T with sodium borohydride, NaBH4.[1] [Total: 10]UCLES 2014 9701/23/O/N/14 [Turn over<br />

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