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NEET CHEMISTRYMedium

Which one of the following reaction sequences is the incorrect method to prepare phenol?

A

Aniline, NaNO2 + HCl, H2O, heating

B

Cumene, O2, H3O+

C

[Option Text Missing]

D

[Option Text Missing]

Step-by-Step Solution

To determine the incorrect method, we analyze the validity of the known options:

  1. From Aniline (Option 1 - Correct Method): Aniline (C6H5NH2C_6H_5NH_2) reacts with nitrous acid (NaNO2+HClNaNO_2 + HCl) at low temperatures (0-5°C) to form benzene diazonium chloride. Upon warming with water, this hydrolyses to form phenol and nitrogen gas.
  2. From Cumene (Option 2 - Correct Method): Cumene (isopropylbenzene) is oxidised in the presence of air (O2O_2) to cumene hydroperoxide. Subsequent hydrolysis with dilute acid (H3O+H_3O^+) converts it into phenol and acetone. This is an important industrial method.
  3. From Haloarenes (Likely context for incorrect option): Chlorobenzene is extremely unreactive towards nucleophilic substitution due to the partial double bond character of the C-Cl bond. It requires drastic conditions (NaOH at 623 K and 300 atm) to form sodium phenoxide, which gives phenol on acidification. If Option 4 suggested preparing phenol from chlorobenzene under mild conditions (e.g., room temperature) or from benzene directly with NaOH, it would be the incorrect method.
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