CIE Mar 2016 v2 Paper 4 Q7

Answers available below

(a) (i) State and explain the relative acidities of ethanol and phenol. 14 PMT[2] (ii) In the table below, give the reaction conditions for the formation of organic products D and E and draw their structures. OH HNO3 Br2 phenol reagent conditions structure HNO3 dilute, 5 C Br2 (iii) Name the mechanism of the reaction forming compound E.[1] [3] (b) (i) Phenylamine reacts with aqueous bromine to give compound F. Describe the appearance of compound F.[1] (ii) Phenylamine reacts with nitrous acid to form a diazonium salt. State the conditions for this reaction.[1]UCLES 2016 9701/42/F/M/16<br /> 15 (iii) The diazonium salt in (ii) reacts with an alkaline solution of phenol to produce a coloured compound, G. Draw the structure of G. PMT (c) Compound H is a primary amine which has three peaks in its carbon-13 NMR spectrum. [2] H3C CH2 NH2 CH2 CH3 compound H (i) An isomer of H is another primary amine J which also has three peaks in its carbon-13 NMR spectrum. Use this information to suggest the structure of J. (ii) Another isomer of H is the tertiary amine K. It has three peaks in its proton NMR spectrum. One of the peaks is a doublet. [1] CH3 H3C CH CH3 CH3 Circle the protons responsible for the doublet.UCLES 2016 9701/42/F/M/16 [1] [Total: 12] [Turn over<br />

Show answer