reactions of nitriles & strong nucleophiles

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Nitriles react with strong nucleophiles like lithium aluminum hydride and organometallics. Lithium aluminum hydride reduces the C-N triple bond of the nitrile all the way down to an amine after the reaction is treated with water. Organometallic reagents, both organolithiums and Grignards, attack the C-N triple bond to make a nitrogen anion intermediate. Upon treatment with water, the N minus is protonated to form a C-N double bond, called an imine. Imines hydrolyze in water to form a ketone, the ultimate product of the reaction of an organometallic reagent on a nitrile.

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