Q39E - Organic Chemistry (Mcmurry)

Question

4- chloropyridine undergoes reaction with dimethylamine to yield 4-dimethylaminopyridine. Propose a mechanism for the reaction.

Step-by-Step Solution

Answer

The mechanism involves 3 steps: The first step is-

• Attack of nucleophile dimethylamine

Step 1: Introduction

The given reaction is an example of nucleophilic aromatic substitution. Where Dimethylamine is a nucleophile and the nitrogen of pyridine acts as an electron-withdrawing group that stabilizes the negatively charged intermediate.

Step 2: Mechanism

The mechanism involves 3 steps:

• Attack of nucleophile dimethylamine

• Loss of proton

• Loss of Cl