Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group. Strong bases are required, such as lithium diisopropylamide and butyl lithium.  The product is referred to as a nitrile anion. These carbanions alkylate a wide variety of electrophiles. Key to the exceptional nucleophilicity is the small steric demand of the CN unit combined with its inductive stabilization. These features make nitriles ideal for creating new carbon-carbon bonds in sterically demanding environments.