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Question
AgCN reacts with haloalkanes to form isocyanide. Haloalkanes react with KCN to form alkyl cyanides as the main product. Why?
Options
AgCN provides cyanide ions in solution.
KCN is mainly covalent in nature.
KCN provides cyanide ions in solution.
AgCN is mainly ionic in nature.
Solution
KCN provides cyanide ions in solution.
Explanation:
AgCN is covalent in nature while KCN is ionic. So KCN produces CN− in the solution. CN− is an ambient nucleophile i.e. it can form bonds from both C and N atoms. KCN is an ionic compound so both C and N sides are available for the formation of a bond, but the C-C bond is stronger than the C-N bond so cyanide is formed. The AgCN is a covalent compound, so only the N side is available for CN to form a bond and thus isocyanide is formed.
