CIE Nov 2016 v2 Paper 4 Q7

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(a) Bromobenzene can be prepared from benzene as shown. 13 Br2 Al Br3 Br PMT (i) Name the mechanism of this reaction.[1] (ii) Draw the mechanism of this reaction. Include all relevant curly arrows, any dipoles and charges. (b) Two isomeric aromatic compounds, V and W, each contain three functional groups, two of which are shown in the table. [4] Br NH CH3 Br NH CH3 Complete the table with the other functional groups present in V and W. substance functional groups present bromo group aryl (benzene) groupbromo group aryl (benzene) group[1]UCLES 2016 9701/42/O/N/16 [Turn over<br /> (c) Compounds V and W can be synthesised from bromobenzene by the following routes. 14 PMT step 2 CH3 PCl 5 step 1 step 3 step 4 NO2 Br CH3COCl Br CH3NH2 NH CH3 NH CH3 (i) Suggest reagents for each of the steps 1 4. step 1step 2step 3step 4[4] (ii) Deduce structures for R, S and T and draw their structural formulae in the boxes. [3] (d) (i) Draw the structures of the two organic products from the reaction of V and W with LiAl H4. Br Br Br product from V product from W [2]UCLES 2016 9701/42/O/N/16<br /> PMT 15 (ii) Name the type of reaction occurring between LiAl H4 and V or W.[1] (e) V and W can be hydrolysed using hot HCl (aq). (i) Draw the structures of the two organic products of the hydrolysis of W. NH CH3 HCl (aq) heat [2] (ii) The products formed from the hydrolysis of W are soluble in aqueous acid, whereas a precipitate, X, is formed on hydrolysing V. Draw the structure of compound X. [1] (iii) Suggest why X is insoluble in water.[1] [Total: 20] BrUCLES 2016 9701/42/O/N/16 [Turn over<br />

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