Question Details

Consider the following reaction:



Products obtained are:

Options

A

B

C

D

Show Answer

Correct Answer :

Option A

Solution :

The reaction shown in the image represents the industrial preparation of phenol, widely known as the Cumene Process.
Let us analyze the reaction step-by-step:

Step 1: Oxidation of Cumene
The starting material shown in Image 0 is cumene (isopropylbenzene), which consists of a benzene ring bonded to an isopropyl group, -CH(CH3)2.
When cumene is oxidized in the presence of oxygen (O2), the tertiary C-H bond of the isopropyl group (which is benzylic and relatively weak) is cleaved to form a stable tertiary benzylic radical. Reaction with oxygen produces cumene hydroperoxide:
C6H5C(CH3)2OOH

Step 2: Acid-Catalyzed Hydrolysis and Rearrangement
In the second step, cumene hydroperoxide is treated with dilute aqueous acid (H2O, H+).
Protonation of the terminal oxygen atom of the hydroperoxide group followed by the loss of a water molecule initiates a rearrangement. The phenyl group migrates from the benzylic carbon to the electron-deficient oxygen atom. Subsequent nucleophilic attack by water and proton transfers yield two major products:
1. Phenol (C6H5OH) - a benzene ring directly attached to a hydroxyl group.
2. Acetone (CH3COCH3) - a key byproduct.

Comparing this with the options provided in the images:
- Option 1 (Image 1) shows the structures of phenol (a benzene ring with an -OH group) and acetone (propan-2-one).
- Option 2 (Image 2) shows benzene and acetone.
- Option 3 (Image 3) shows phenol and propan-2-ol.
- Option 4 (Image 4) shows benzene and propan-2-ol.

Therefore, the correct products obtained are phenol and acetone, as represented in the first option.

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