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NEET CHEMISTRYMedium

The structure of intermediate A in the following reaction is: Cumene→O2A→H3O+Phenol+Acetone\text{Cumene} \xrightarrow{O_2} A \xrightarrow{H_3O^+} \text{Phenol} + \text{Acetone}

A

C6H5−CH(CH3)2C_6H_5-CH(CH_3)_2

B

C6H5−CO−CH3C_6H_5-CO-CH_3

C

C6H5−CH(OH)−CH3C_6H_5-CH(OH)-CH_3

D

C6H5−C(CH3)2−O−OHC_6H_5-C(CH_3)_2-O-OH

Step-by-Step Solution

The reaction shown is the industrial method for the preparation of phenol from Cumene (isopropylbenzene).

  1. Oxidation: Cumene is oxidised in the presence of air to form Cumene hydroperoxide (Intermediate A). In this step, the tertiary hydrogen atom of the isopropyl group is replaced by a hydroperoxy group (−O−OH-O-OH).
  2. Hydrolysis: The intermediate Cumene hydroperoxide is then treated with dilute acid (H3O+H_3O^+), which causes it to undergo rearrangement and hydrolysis to yield Phenol and Acetone (propan-2-one) as a valuable by-product.

Structure of A: Isopropylbenzene where the CHCH bond is converted to C−O−O−HC-O-O-H.

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