High School

How is it that a ketone reacts with a Grignard reagent to form a tertiary alcohol, but in the reaction of a nitrile with a Grignard reagent, a ketone is formed?

A. Tautomerism
B. Nucleophilic addition
C. Electrophilic addition
D. Rearrangement

Answer :

Final answer:

A ketone reacts with a Grignard reagent through nucleophilic addition to form a tertiary alcohol. In the reaction of nitrile with a Grignard reagent, a ketone is formed through a similar nucleophilic addition mechanism.

Explanation:

The reaction between a ketone and a Grignard reagent results in the formation of a tertiary alcohol through nucleophilic addition. The Grignard reagent, which acts as a strong nucleophile, attacks the electrophilic carbon of the ketone, leading to the formation of an alkoxide intermediate. This intermediate is then protonated to produce the tertiary alcohol.

On the other hand, when a nitrile reacts with a Grignard reagent, a ketone is formed through a similar mechanism of nucleophilic addition. The Grignard reagent attacks the electrophilic carbon of the nitrile, forming an imine salt intermediate. This intermediate undergoes hydrolysis to yield the ketone product.