Chemistry · Ch 13 — Amines
Alkylation
Alkylation
Because amines are good nucleophiles, they can attack an alkyl halide directly in a nucleophilic substitution reaction, displacing the halide and installing a new alkyl group on nitrogen:
The product of this first substitution is itself still a nucleophilic amine (now secondary), so it does not stop there — it can go on to react with a further equivalent of the alkyl halide, and the resulting tertiary amine can react again to give a quaternary ammonium salt. In other words, alkylating a primary amine with an alkyl halide tends to march the nitrogen straight through primary secondary tertiary quaternary ammonium salt, all under essentially the same reaction conditions, since each successive amine remains a competent nucleophile towards the alkyl halide still present. …