CIE Jun 2013 v2 Paper 2 Q5

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Examiners For Use 10 A student reacted together an alcohol and a carboxylic acid under appropriate conditions to produce an ester. A sweet smelling organic liquid, Q, with the empirical formula C2H4O was produced. The Mr of Q was found by experiment to be 87.5. (a) What is the molecular formula of Q?[1] (b) In the boxes below, draw the structural formulae of four isomers with this formula that are esters. [4]UCLES 2013 9701/22/M/J/13<br /> Examiners For Use 11 A sample of Q was hydrolysed by heating with aqueous sulfuric acid. The resulting mixture was heated under re ux with acidi ed potassium dichromate(VI) to give a single organic product, R. The product, R, was collected and subjected to the following tests. A sample of R gave no reaction with Tollens reagent. A second sample of R gave no reaction with 2,4-dinitrophenylhydrazine reagent. A third sample of R gave an effervescence with sodium carbonate. (c) (i) What does the result of the test with Tollens reagent show about R?(ii) What does the result of the test with 2,4-dinitrophenylhydrazine reagent show about R?(iii) What functional group does the result of the test with sodium carbonate show to be present in R?[3] (d) (i) What is the identity of the single organic compound, R?(ii) Which of your structures, W, X, Y or Z, represents the ester, Q?[2] (e) Which, if any, of your esters, W, X, Y or Z, is chiral?[1] [Total: 11]UCLES 2013 9701/22/M/J/13 [Turn over<br />

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