Chapter 23, Problem 23.52P

Interpretation Introduction

Interpretation:

Phenol undergoes three successive brominations even without a strong Lewis acid catalyst, but anisole undergoes single bromination under similar condition is to be explained.

Concept introduction:

Bromination is an electrophilic aromatic substitution reaction where the aryl compound reacts with ${\text{Br}}_{\text{2}}$ in the presence of Lewis acid catalyst. If the substituent attached to the aromatic ring is highly electron donating, then it activates the ring strongly and undergoes successive bromination even without Lewis acid catalyst. If the substituent has less electron donating effect, then the reaction stops after single bromination.