In the commercial preparation of phenol, a specific aromatic hydrocarbon is oxidized in the presence of air to form a hydroperoxide intermediate. This intermediate, upon subsequent treatment with dilute acid, yields phenol and acetone as the final products. Identify the starting aromatic hydrocarbon.

Step-by-step solution

The commercial preparation of phenol yielding acetone as a valuable by-product is known as the cumene process. The starting material for this process is cumene, which is the common name for isopropylbenzene. It is oxidized in the presence of air to form cumene hydroperoxide at the benzylic position. This intermediate is then converted to phenol and acetone by treating it with dilute acid. n-Propylbenzene, ethylbenzene, and toluene do not form cumene hydroperoxide and would not yield acetone upon oxidation and subse