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(e) The Syl reaction of chloride 15 with HBr is shown below, answer both parts (i) and (ii). Me OMe OMe HBr HBr Phy CI

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(e) The Syl reaction of chloride 15 with HBr is shown below, answer both parts (i) and (ii). Me OMe OMe HBr HBr Phy CI Ph Ph Br Me Me Me 15 16 17 (i) With the aid of suitable diagrams explain the different effects which stabilise the intermediate carbenium ion, 16. [16%] (ii) Explain why bromide 17 is racemic even though chloride 15 is a single enantiomer. [4%]

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