We saw in Section 17-4 that ketones react with NaBH4 to yield alcohols. Well also see in

Chapter 18, Problem 18

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

Equation Transcription:

Text Transcription:

NaBH4

Br2

\alpha

NaBH4

\alpha

CH3

Br2

CH2Br

NaBH4

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