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  4. Isocyanide can be prepared from alkyl halide on treatment with

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Q. Isocyanide can be prepared from alkyl halide on treatment with

VMMC MedicalVMMC Medical 2010

Solution:

$ R-X+KCN\xrightarrow{{}}\underset{\begin{smallmatrix} \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\text{alkyl}\,\text{cyanide} \\ \text{(attack}\,\text{occurs}\,\text{through}\,\text{C)} \end{smallmatrix}}{\mathop{RCN}}\, $ $ R-X+AgCN\xrightarrow{{}}\underset{\begin{smallmatrix} \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\text{alkyl} \\ \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\text{isocyanide} \\ \text{(attack}\,\text{occurs}\,\text{through}\,\text{N)} \end{smallmatrix}}{\mathop{R-NC}}\, $ $ \text{AgCN} $ is predominantly covalent, therefore, in this case only N-atom is free to donate electron pair. Thus, the attack mostly occurs through the N-atom of the cyanide group forming alkyl isocyanides. $ C{{N}^{-}} $ behaves as an ambidentate nucleophile.