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KCET2016ChemistryAlcohols Phenols and Ethers

Replacement of ( Cl ) of Chlorobenzene to give phenol requires drastic conditions, but ( Cl ) of ( 2,4 ) - dinitro chlorobenzene is readily replaced. This is because,

Options

  1. A( - NO ₂ ) group makes the ring electron rich at o- and p- positions.
  2. B(- NO ₂ ) group withdraws electrons from ( m )-position.
  3. C( - NO ₂ ) donate electrons at ( m ) - position.
  4. D( - NO ₂ ) withdraws electrons from o- and p-positions.

Correct answer

D. ( - NO ₂ ) withdraws electrons from o- and p-positions.

Step-by-step solution

The reaction involved is The presence of ( - NO ₂ ) group at o- and p- positions withdraws electron density from the benzene ring, therefore, facilitates the attack of the nucleophile on haloarenes. Thus, the carbanion formed, is stabilized through resonance as shown below:

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