CIE Jun 2017 v3 Paper 4 Q5

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12 Compounds J, K, L and M are isomers of each other with the molecular formula C9H11NO. All four isomers contain a benzene ring. Two of the isomers contain a chiral centre. The results of six tests carried out on J, K, L and M are shown in the table. PMT test add cold HCl (aq) add 2,4-DNPH reagent add NaOH(aq) + I2(aq) 1 2 3 4 warm with Fehlings observations with each isomer soluble soluble orange ppt. orange ppt. pale yellow ppt. no reaction no reaction red ppt. M insoluble soluble orange ppt. no reaction pale yellow ppt. no reaction no reaction no reaction solution heat with NaOH(aq) no reaction no reaction no reaction diazotization and addition of alkaline phenol no dye produced orange dye produced no dye produced P(C6H7N) and Q(C3H5O2Na) produced no dye produced (a) Use the experimental results in the table above to determine the group(s), in addition to the benzene ring, present in each of the four isomers J, K, L and M. Complete the table below, identifying the group(s) present in each isomer. group(s) in compound[5]UCLES 2017 9701/43/M/J/17<br /> 13 (b) (i) Name the type of reaction occurring in test 5 that converts M into P + Q.[1] (ii) Suggest structures for compounds P and Q. PMT P (C6H7N) Q (C3H5O2Na) [2] (c) Isomers J, K, L and M all have the molecular formula C9H11NO. Use the information in (a) to suggest a structure for each of these isomers and draw these in the boxes. Draw circles around all chiral centres in K and L. (d) Compound N is another isomer which has the same molecular formula C9H11NO and also contains a benzene ring. N contains the same functional group as M. When heated with NaOH(aq), N produces ethylamine and a sodium salt W. Suggest the structure of W. [5]UCLES 2017 9701/43/M/J/17 [1] [Total: 14] [Turn over<br />

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