9. (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.
9. (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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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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![H
9. (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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F940a64b6-a53e-4bc6-85b0-cc0b37fb57fe%2F7c1e9874-07b0-41e1-8917-127722a97ee9%2Fq7imdoj_processed.jpeg&w=3840&q=75)
Transcribed Image Text:H
9. (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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