CIE Mar 2016 v2 Paper 4 Q8

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Acebutolol is a drug that can be used to lower blood pressure. 16 H3C N H OH H N CH3 CH3 CH3 acebutolol (a) Give the full name of the circled functional groups labelled P, Q and R in acebutolol. PQR(b) On the diagram of acebutolol below, draw a circle around any chiral carbon atoms. H3C N H OH H N CH3 CH3 CH3 (c) On warming with dilute hydrochloric acid, acebutolol splits to form two molecules. (i) Draw a line through the bond broken by heating with dilute hydrochloric acid. (ii) Draw the structure of the smaller molecule produced by this reaction. PMT [3] [1] [1] [1]UCLES 2016 9701/42/F/M/16<br /> 17 (d) Suggest what would be observed when acebutolol reacts with the following reagents. If no reaction would take place, write none in the table below. reagent observation PMT alkaline iodine solution universal indicator solution 2,4-dinitrophenylhydrazine Tollens reagent (e) Butanoic acid can be reduced to form compound N. Compound N reacts with sodium. (i) Suggest a suitable reducing agent for this reaction.[1] (ii) Draw the skeletal formula of the isomer of N that exists as a pair of optical isomers. [3] (iii) Another isomer of N does not react with acidified dichromate(VI) solution but does react with sodium. Draw the structure of this isomer. [1] [1] [Total: 12]UCLES 2016 9701/42/F/M/16 [Turn over<br />

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