Reaction of Nitriles with Organometaliic Reagents

Grignard reagents can attack the electophillic carbon in a nitrile to form an imine salt. This salt can then be hydrolyzed to become a ketone.

General Reaction

Example

Mechanism

1) Nucleophilic Attack by the Grignard Reagent

2) Protonation

3) Protonation

4) Nucleophilic attack by water

5) Proton Transfer

6) Leaving group removal

7) Deprotonation