JEE Main · 2024 · 29 Jan 2024 · Shift 2 · Compounds Containing Nitrogen

Alkyl halide is converted into alkyl isocyanide by reaction with

(A)NaCN
(B) $NH_{4} CN$
(C)KCN
(D)AgCN✓ Correct

Answer: (D)

Solution

Cyanide is an ambident nucleophile that can bond through either its carbon or its nitrogen end. With ionic cyanides such as NaCN or KCN, the more nucleophilic carbon end attacks the alkyl halide in an

S_{N} 2

reaction, giving the nitrile (alkyl cyanide, R–CN).

AgCN is predominantly covalent, with cyanide already bonded to silver through carbon; this leaves the nitrogen end as the available nucleophile, so reaction with an alkyl halide proceeds through nitrogen instead:

R - X + AgCN \to R - NC + AgX

AgCN converts an alkyl halide into the alkyl isocyanide.

JEE Main · 2024 · 29 Jan 2024 · Shift 2 · Single correct option

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