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Q.
$ C{{H}_{3}}O{{C}_{2}}{{H}_{5}} $ and $ {{(C{{H}_{3}})}_{3}}COC{{H}_{3}} $ are treated with $ HI $ . The fragments after reaction obtained are
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Solution:
$ C{{H}_{3}}O{{C}_{2}}{{H}_{5}} $ undergoes cleavage by $ {{S}_{N}}2 $ mechanism to give $ C{{H}_{3}}l $ and $ {{C}_{2}}{{H}_{5}}OH $ while $ {{(C{{H}_{3}})}_{3}}COC{{H}_{3}} $ undergoes cleavage by $ {{S}_{N}}1 $ mechanism to give $ {{(C{{H}_{3}})}_{3}}Cl $ and $ C{{H}_{3}}OH $ .