a. sec-butyl alcohol remains optically active in aqueous base, but racemizes whenmixed with dilute sulfuric acid. Suggest a mechanism accounting for thisobservation.b. The following 1935 experiment established that in SN2 reactions, a moleculeundergoes an inversion of configuration. Optically active 2-iodooctane wasreacted to with Na1311 in acetone. It was observed that the rate of reactiondepended on both [RI] and [I-], but the rate of racemization was two times fasterthan isotopic exchange. Explain this set of results.c. Explain the following observations: (i) why neomenthyl chloride and menthylchloride yields the following products below; and, (ii) why menthyl chloride reacts1/200 times as fast as neomenthyl chloride to yield the same product asneomenthyl chloride.daCneomenthyl chloride2-menthene25%2-menthene75%menthyl chloride2-mentheneonly product

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Answered: a. sec-butyl alcohol remains optically…

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.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.37P

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Question

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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