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We saw in Section 17-4 that ketones react with NaBH 4 to yield alcohols. We’ll also see in Section 22-3 that ketones react with Br 2 to yield α-bromo ketones. Perhaps surprisingly, treatment with NaBH 4 of the α -bromo ketone from acetophenone yields an epoxide rather than a bromo alcohol. Show the structure of the epoxide, and explain its formation.

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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 18.SE, Problem 68GP
Textbook Problem
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We saw in Section 17-4 that ketones react with NaBH4 to yield alcohols. We’ll also see in Section 22-3 that ketones react with Br2 to yield α-bromo ketones. Perhaps surprisingly, treatment with NaBH4 of the α -bromo ketone from acetophenone yields an epoxide rather than a bromo alcohol. Show the structure of the epoxide, and explain its formation.

Chapter 18.SE, Problem 68GP, We saw in Section 17-4 that ketones react with NaBH4 to yield alcohols. We’ll also see in Section

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.

Explanation of Solution

The nucleophilic attack of the hydride ion from NaBH4 on the carbonyl carbon in the bromoacetophenone leads to the formation of an oxyanion intermediate. In the next step an internal nucleophilic attack by the negatively charged ...

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Chapter 18 Solutions

Organic Chemistry
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