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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr
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(a) Optically active 2-bromobutane undergoes racemization

Chapter 8, Problem 59SP

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QUESTION:

Problem 59SP

(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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QUESTION:

Problem 59SP

(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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Solution 59SP

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