Question

The major product formed in the following reaction sequence is
 

 

• A. 1
• B. 2
• C. 3
• D. 4

Hint:

The sequence \[ \text{Benzene} \rightarrow \text{Cumene} \rightarrow \text{Cumene Hydroperoxide} \rightarrow \text{Phenol} \] is known as the Cumene Process, the most important industrial method for the manufacture of phenol.

Answer 1

The Correct Option is A

This sequence is really just the industrial cumene process for making phenol, told in two steps.

First, benzene reacts with isopropyl chloride using AlCl3 as a Friedel-Crafts alkylation catalyst, attaching an isopropyl group to the ring to give cumene, that is isopropylbenzene.

Cumene then reacts with atmospheric oxygen to form cumene hydroperoxide, and treating that peroxide with dilute acid triggers a rearrangement that cleaves it into two products at once, phenol and acetone.

Since the question asks for the major aromatic product of the whole sequence, that is phenol, with acetone coming along as the by-product.

So the correct choice is option (1).