Question

Alkylation of amines with alkyl halides proceeds by _________

(a) electrophilic addition

(b) electrophilic substitution

(c) nucleophilic addition

(d) nucleophilic substitution

This question was posed to me during a job interview.

My doubt stems from Amines Chemical Reactions topic in chapter Amines of Chemistry – Class 12

Answer 1

Right option is (d) nucleophilic substitution

For explanation I would say: The amines itself acts as nucleophiles and attack the alkyl halide at the carbon-halogen bond to substitute the halogen atom by itself. This occurs by production of small amount of acid at each step, which may prevent the reaction by proceeding by protonating the amine.