Given that the treatment of α-bromoacetophenone, obtained from acetophenone by bromination, with NaBH 4 yields an epoxide . The structure of the epoxide is to be shown and its formation is to be explained. Concept introduction: The nucleophilic attack attack of the hydride ion on the carbonyl carbon of the bromoketone and the following internal nucleophilic attack by the negatively charged oxide ion and to eliminate a bromide ion will lead to the formation of the epoxide. To give: Given that the treatment of α-bromoacetophenone, prepared from acetophenone, with NaBH 4 yields an epoxide. The structure of the epoxide is to be shown and its formation is to be explained.

Question

What would be a proposed mechanism to get from cyclohexanol to cis-2-methoxycyclohexanol? I know how to get from cyclohexanol to trans-2-methoxycyclohexanol would be to go through acid-catalyzed dehydration via H2SO4, then epoxide ring formation via mCPBA and then alcohol-catalyzed opening, but don't know how to do for the cis version, if possible.

Answer 1

Question

Chapter 18.SE, Problem 68GP

Interpretation Introduction

Interpretation:

Given that the treatment of α-bromoacetophenone, obtained from acetophenone by bromination, with NaBH₄ yields an epoxide. The structure of the epoxide is to be shown and its formation is to be explained.

Concept introduction:

The nucleophilic attack attack of the hydride ion on the carbonyl carbon of the bromoketone and the following internal nucleophilic attack by the negatively charged oxide ion and to eliminate a bromide ion will lead to the formation of the epoxide.

To give:

Given that the treatment of α-bromoacetophenone, prepared from acetophenone, with NaBH₄ yields an epoxide. The structure of the epoxide is to be shown and its formation is to be explained.

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