Write the mechanism of the following reaction.

$n B u B r + K C N E i O H - H_{2} O - ------ \to n B u C N$

Write the resonating structures of KCN.

Due to the presence of polar solvent, find the possiblity, which product will be formed preferentially ?

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Solution

Resonating forms of KCN are the following

Cyanide ion is an ambident nucleophile. It can attack through C-atom or through N-atom. Thus, two possible products are cyanides and isocyanides respectively. Here in the presence of the polar solvent, KCN readily ionises to furnish ions. As the C-C bond is more stable than the C-N bond, so cyanide is predominantly formed.

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