Which of the following functional groups does not afford an alcohol when treated with a Grignard reagent followed by a protic work-up.
A) ketone
B) aldehyde
C) ester
D) epoxide
E) nitrile

Question

Quizplus · Accepted Answer

Treatment of ketones, aldehydes, and esters with Grignard reagents followed by a protic work-up affords alcohols. Epoxides also react with Grignard reagents to give alcohols upon hydrolysis of the resulting alkoxide intermediate. However, nitriles do not yield alcohols upon treatment with Grignard reagents due to the formation of imine intermediates, which do not undergo hydrolysis to give alcohols.

Which of the Following Functional Groups Does Not Afford an Alcohol