The two compounds V and W are isomers withthe molecular formula C,H,O, and show the folowing properties and reactions. Both compounds react with sodium metal, and both decolotrise bromine water. ‘Compound V forms a yellow precipitate with alkaline aqueous iodine, whereas compound W does not When reacted with cold KMnO,(aq), both V and W produce the same neutral compound CHO, + Both Vand W exist as pairs of sterecisomers, (a) Suggest which functional groups are responsible forthe reactions with (0 sodium, (li) bromine wate {li elkeline aqueous iodine. (©) Suggest structures for Vang W. a{€) State the type of stereoisomerism shown by compound V and draw the stuctures of the storeoisomers. type of stereoisomerism structures of stereoisomers, isomer 1 isomer 2 {d) Suggest the structure of the neutral compound X el tl (Total: 8)Although now remembered for is music, the Russian composer Alexander Borodin was a chemist. He is erecited with the discovery of the aldol reaction, @ product of whieh is compound J J shows the following properties: its molecular formula is CLH,O., itis neutral IRreaets with sodium metal, Itreacts with Fehiing’s solution, it does not react with aqueous bromine. {(@) Suggest which functional groups are responsible forthe reactions with {i) sodium, (ii) Fehing’s solution {(b) The resuit of the bromine test shows a functional group is absent from comecund J. ‘Suggest the identity ofthis functional group. m (0) In the boxes belo, draw three possible straight-chain structures for J that ft the above results, and that are structural isemers of aach other(6) Compound J reacts wth alkaline aqueous iodine to give a pale yellow precipitate () Which functional group does this reaction show that J contains? (i) Which of your three structures K, L or M contains this group and is therefore J? a (e) Compound J esas os stereoisomers (0) Name the typeof serelsomersm shown by J (ii) Draw two structures of J to illustrate this stereoisomerism. 2 [Tota’: 10)(Organic chemisty is the chemistry of carbon compounds. The types of organic reactions that you have studied are listed below. addition elimination hydrolysis oxidation reduction substitution Adktion and substitution reactions are further descnbed as follows electrophilic nucleophile {ree radical Complete the table below Fillin the central colurnn by using only the types of reaction given in the lists above. Use both lists when appropriate, In the right hang column give the formulae) of the reagents) you would use to cary out the reaction given frganie reaction type of reaction reagentis} CH,CH.CH.CH.2r — CHC, HNHs CH,CH.CH.CH.OH — BrCH,CH,CH.CH.OH cH.COCH, + ‘CH,C/OH)CNICH, CH.CH(OH)CH.CH, = (CH,CH=CHCH, (Total: 11)A Compound X has the molecular formula C,H,0, (a) Treatment of X with sodium metal produces a colourless flammable gas. ‘What does this resut tell you about the funetional groups that could be presentin X? (ll) There is no reaction when X is trested with sodium hydrogencarbonate, NaHCO, ‘What does this result tell you about the functional groups that could be presentin X? (ll) When Xs shaken wth aqueous bromine the orange colour disappears, |What does this result tell you about the functional groups that could be presentin X? a