1. Kindly answer the following questions below. You may use illustration to help explain your answers [. 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: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
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1. Kindly answer the following questions below. You may use illustration to help explain
your answers.
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.
2022
a
C/
neomenthyl chloride
2-menthene
25%
2-menthene
75%
menthyl chloride
2-menthene
only product
Transcribed Image Text:1. Kindly answer the following questions below. You may use illustration to help explain your answers. 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. 2022 a C/ neomenthyl chloride 2-menthene 25% 2-menthene 75% menthyl chloride 2-menthene only product
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