CIE Nov 2014 v2 Paper 4 Q5

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(a) Organohalogen compounds can undergo hydrolysis. 12 PMT RCl + H2OROH + HCl State the relative rates of hydrolysis of the following compounds. CH3CH2CH2Cl CH3CH2COCl C6H5Cl Explain your answer.[3] (b) Aminolaevulinic acid is involved in the synthesis of haemoglobin and chlorophyll. OH H2N aminolaevulinic acid Name the three functional groups in aminolaevulinic acid.[2] (c) Aminolaevulinic acid reacts readily with bromoethane. (i) Show the mechanism of therst step of this reaction on the diagram. Include all necessary curly arrows, lone pairs and relevant dipoles. OH intermediate OH HN H3C H2N H3C CH2 BrUCLES 2014 9701/42/O/N/14<br /> PMT 13 (ii) Name the mechanism in (c)(i).(iii) Identify the non-organic product formed in this reaction.[5] (d) Three reactions of aminolaevulinic acid are shown. Draw the structures of the products W, X and Y in the boxes below. OH H2N aminolaevulinic acid HCl (aq), warm NaBH4 CH3COCl (e) Aminolaevulinic acid can undergo polymerisation. Draw the structure of the polymer showing two repeat units. The linkages between the monomer units should be shown fully displayed. [3]UCLES 2014 9701/42/O/N/14 [2] [Total: 15] [Turn over<br />

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