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------------------------------------------------ Which of the following functional groups does not afford an alcohol when treated with a Grignard reagent followed by a protic work-up?

A. Epoxide
B. Nitrile
C. Aldehyde
D. Ketone
E. Ester

The functional group that does not afford an alcohol when treated with a Grignard reagent followed by a protic work-up is the epoxide group. When an epoxide reacts with a Grignard reagent, it forms a different compound known as a phenol.

Explanation:

The functional group that does not afford an alcohol when treated with a Grignard reagent followed by a protic work-up is the epoxide group. When an epoxide reacts with a Grignard reagent, it forms a different compound known as a phenol. This is because the nucleophilic attack of the Grignard reagent occurs at the oxygen of the epoxide, resulting in the formation of a phenol instead of an alcohol.

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