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Haloakanes react with KCN to form alkyl ...

Haloakanes react with KCN to form alkyl cyanides as main product while AgCN forms isocyanides as the chief product . Explain .

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KCN is predominantly ionic and provides cyanide ions in solution . Although both carbon and nitrogen atoms are in a position to donate electron pairs , the attack takes place mainly through carbon atom and not through nitrogen atom since `C- C` bond is more stable than `C- N` bond . however , AgCN is mainly covalent in nature and nitrogen is free to donate electron pair forming isocyanide as the main product .
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