CIE Mar 2016 v2 Paper 2 Q5

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PMT Some reactions of compound P, C5H8O, are shown. 12 compound Q H2(g) Ni(s) catalyst compound R NaBH4 cold, acidified KMnO4(aq) compound S compound P OH(aq) I2(aq) O compound T + (a) (i) Give the structures for organic compounds Q, R, S and T.UCLES 2016 9701/22/F/M/16 [4]<br /> PMT (ii) Give the systematic name of compound P. 13[1] (iii) What would you observe when compound P is reacted with 2,4-dinitrophenylhydrazine (2,4-DNPH)?[1] (b) Compound U contains a chiral centre and has the same molecular formula as compound P, C5H8O.Compound U readily decolourises a sample of bromine water. Compound U does not show cis-trans isomerism. When compound U is heated under reflux in the presence of excess acidified potassium dichromate(VI), the organic product gives the infra-red spectrum shown. infra-red spectrum of product 100 transmittance / 50 0 4000 3000 2000 1500 wavenumber / cm1 1000 500 Use the information given to suggest a structure for compound U. Explain your answer.UCLES 2016 9701/22/F/M/16 [4] [Total: 10] [Turn over<br />

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