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resonance for nitrile


addition of potassium cynaide to alkyl halide
nitrile; SN2


acidic workup of nitrile
carboxylic acid and ammonium; begins with protonation of nitrogen


basic workup of nitrile
deprotonated carboxylic acid and ammonia


addition of organolithium to nitrile
ketone; nucleophlic attack on nitrile carbon; iminium ion

addition of organolithium to nitrile mechanism


lithium aluminium hydride reduction of nitrile
amine


amine
