Chapter 10, Problem 10.34P

Interpretation Introduction

Interpretation:

The reactant of the given reaction whose formula is ${\text{C}}_{\text{10}}{\text{H}}_{\text{16}}\text{ClN}$ is to be drawn.

Concept introduction:

In alkylation at the N atom, the excess of alkyl halide reacts with amines. With excess alkyl halide, the reaction occurs several times. The primary amine that is formed from the alkylation of ammonia is nucleophilic at the N atom. It reacts with any unreacted alkyl halide species, leading to further alkylations. The same process, i.e., an ${\text{S}}_{\text{N}}\text{2}$ reaction followed by deprotonation can occur a second time to yield the tertiary amine. The tertiary amine is nucleophilic, too, so it can react in a third ${\text{S}}_{\text{N}}\text{2}$ reaction to yield the quaternary ammonium ion.