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Reaction of Organometallic Compounds with Nitriles

The nitrile group is electron-deficient at carbon and can therefore be attacked by organometallic compounds, forming a new C–C bond.

Nitriles and orgamometallics▶ Watch the video on YouTube
Reaction of benzonitrile with methylmagnesium bromide and hydrolysis of the imine: acetophenone

The addition product is an imine, which is easily hydrolyzed to the corresponding ketone with loss of ammonia. We will study imines later.