Question: (a) Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. Give a mechanism for this racemization. (b) In contrast, optically active butan-2-ol

(a) Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. Give a mechanism for this racemization.
(b) In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that in part (a) does not occur.
(c) Optically active butan-2-ol racemizes in dilute acid. Propose a mechanism for this racemization.

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a An S N 2 mechanism with inversion will convert R to its enantiomer S An accumulation ... View full answer

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