Chapter 19.10C, Problem 19.13P

Interpretation Introduction

Interpretation:

The mechanism for the reaction of methoxide ion with $\text{4-chloropyridine}$ at position $4$ is to be stated and how the intermediate is stabilized by delocalisation of the charge onto the nitrogen atom is to be shown.

Concept introduction:

The reactions in which a nucleophile replaces a leaving group (for example, halide) on an aromatic ring is known as nucleophilic aromatic substitution. A carbocation intermediate is formed in these reactions. Electron withdrawing groups on the aromatic ring destabilize the carbocation intermediate whereas, electron donating groups on the aromatic ring stabilize the carbocation intermediate.