Question

Account for the following :

(a) Haloalkanes react with NaCN to form both cyanides and isocyanides.

(b) Haloarenes do not undergo nucleophilic substitution reaction easily.

(c) Benzyl chloride gives S_N1 reaction.

Answer 1

(a) Haloalkane react with NaCN to form cyanides (major product) and isocyanides (minor product) because CN– is an ambidentate ligand and it can attack either by C centre or N centre.

(b) C – Cl bond acquires a partial double bond character due to resonance, so haloarenes do not undergo nucleophilic substitution reaction easily.

(c) Benzyl chloride gives S_N1 reaction because the carbocation formed gets stabilised through resonance.