Edexcel Jun 2012 Paper 2 Q18

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18 The steps below show the reaction mechanism for the reaction of a halogenoalkane with sodium hydroxide in aqueous solution to form an alcohol. CH3 H3C C Cl CH3 H3C C(cid:1206)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)+(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)Cl(cid:1214) CH3 CH3 CH3 H3C C(cid:1206)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)(cid:2)OH(cid:1214) CH3 CH3 H3C C OH CH3 (a) (i) Name X and Z. (2) XZ(ii) Draw the skeletal formula of X. (iii) What type of alcohol is Z? (1) (1)12 *P39307A01220*<br /> (b) (i) Name the mechanism and type of reaction shown above. (2)(ii) Explain what the curly arrows shown in the mechanism represent. (1)*(iii) Suggest the shape of the intermediate Y. Explain your answer. (3)(iv) If the reaction is carried out in alcoholic (ethanolic) rather than aqueous solution, a different type of reaction occurs and a different product is formed. Name the type of reaction that occurs in alcoholic (ethanolic) solution and identify the product by name or formula. (2) Type of reaction Product *P39307A01320* 13 Turn over<br /> (c) The alcohol Z (shown below) resists oxidation. However, Z has three structural isomers which are readily oxidized. On complete oxidation, one isomer forms a ketone and the other two isomers form carboxylic acids. CH3 H3C C OH CH3 Z (i) Draw the structural formula of the isomer of Z that forms a ketone. (ii) Draw the structural formulae of the isomers of Z that form carboxylic acids. (1) (2) (Total for Question 18 = 15 marks) 14 *P39307A01420*<br />

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