A) \[\text{AgCN}\]
B) \[\text{AgNC}\]
C) \[\text{KCN}\]
D) None of these
Correct Answer: A
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.
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