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a. sec-butyl alcohol remains optically active in aqueous base, but racemizes when mixed with dilute sulfuric acid. Suggest a mechanism accounting for this observation.

a. sec-butyl alcohol remains optically active in aqueous base, but racemizes when mixed with dilute sulfuric acid. Suggest a mechanism accounting for this observation.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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a. sec-butyl alcohol remains optically active in aqueous base, but racemizes when mixed with dilute sulfuric acid. Suggest a mechanism accounting for this observation. b. The following 1935 experiment established that in SN2 reactions, a molecule undergoes an inversion of configuration. Optically active 2-iodooctane was reacted to with Na1311 in acetone. It was observed that the rate of reaction depended on both [RI] and [I-], but the rate of racemization was two times faster than isotopic exchange. Explain this set of results. c. Explain the following observations: (i) why neomenthyl chloride and menthyl chloride yields the following products below; and, (ii) why menthyl chloride reacts 1/200 times as fast as neomenthyl chloride to yield the same product as neomenthyl chloride. da C neomenthyl chloride 2-menthene 25% 2-menthene 75% menthyl chloride 2-menthene only product
Transcribed Image Text:a. sec-butyl alcohol remains optically active in aqueous base, but racemizes when mixed with dilute sulfuric acid. Suggest a mechanism accounting for this observation. b. The following 1935 experiment established that in SN2 reactions, a molecule undergoes an inversion of configuration. Optically active 2-iodooctane was reacted to with Na1311 in acetone. It was observed that the rate of reaction depended on both [RI] and [I-], but the rate of racemization was two times faster than isotopic exchange. Explain this set of results. c. Explain the following observations: (i) why neomenthyl chloride and menthyl chloride yields the following products below; and, (ii) why menthyl chloride reacts 1/200 times as fast as neomenthyl chloride to yield the same product as neomenthyl chloride. da C neomenthyl chloride 2-menthene 25% 2-menthene 75% menthyl chloride 2-menthene only product
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