CIE Jun 2014 v3 Paper 4 Q5

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PMT 12 The two compounds V and W are isomers with the molecular formula C4H8O, and show the following properties and reactions.Both compounds react with sodium metal, and both decolourise bromine water. Compound V forms a yellow precipitate with alkaline aqueous iodine, whereas compound W does not. When reacted with cold KMnO4(aq), both V and W produce the same neutral compound X, C4H10O3. Both V and W exist as pairs of stereoisomers. (a) Suggest which functional groups are responsible for the reactions with (i) sodium,(ii) bromine water,(iii) alkaline aqueous iodine.[3] (b) Suggest structures for V and W. [2]UCLES 2014 9701/43/M/J/14<br /> 13 (c) State the type of stereoisomerism shown by compound V and draw the structures of the stereoisomers. type of stereoisomerismstructures of stereoisomers PMT isomer 1 isomer 2 [2] (d) Suggest the structure of the neutral compound X. [1] [Total: 8]UCLES 2014 9701/43/M/J/14 [Turn over<br />

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