Acidic hydrolysis of alkyl isocyanide gives rise to primary amines and formic acid. But alkyl isocyanides do not undergo hydrolysis in basic medium. Why?
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1 Answer
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The main reason for the inability of alkyl isocyanides to undergo hydrolysis in basic medium is because the negative charge at the carbon atom $(\ce{R-\overset{+}{N}#\overset{-}{C}\!:})$ repels the nucleophile $\ce{OH-}$ due to both being negatively charged. See this answer for more information.
answered Aug 12, 2021 at 12:21