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Which amongst the following reactions of alkyl halides produces isonitrile as a major product? (A) R–X + HCN $\rightarrow$ (B) R–X + AgCN $\rightarrow$ (C) R–X + KCN $\rightarrow$ (D) R–X + NaCN $\xrightarrow{H_2O/C_2H_5OH}$
A
(D) only
B
(C) and (D) only
C
(B) only
D
(A) and (B) only
Detailed Solution
$AgCN$ has a covalent character with the carbon of cyanide primarily bonding via nitrogen due to steric/electronic factors, so reaction of an alkyl halide with $AgCN$ produces the isonitrile (isocyanide) as the major product: $R-X+Ag-C\equiv N\rightarrow R-NC$. Reaction with $KCN$ or $NaCN$ (more ionic) predominantly gives the nitrile ($R-CN$) as the major product via the more nucleophilic carbon end.