Chapter 13.5, Problem 5P

Interpretation Introduction

Interpretation:

A reasonable mechanism is to be written for the given reaction of benzene with $\text{acetyl}\text{hypoiodite}$.

Concept introduction:

On iodination with $\text{acetyl}\text{hypoiodite}$, benzene undergoes an electrophilic aromatic substitution where a hydrogen atom of the aromatic ring is substituted by an iodine atom.

The $\text{acetyl}\text{hypoiodite}$ acts as an electrophile while the aromatic ring acts as a nucleophile.

The attack of aromatic $\text{π}$ electrons on iodine atom of $\text{acetyl}\text{hypoiodite}$ is the slow step. Therefore, this step is the rate determining step.