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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Arrange the following compounds in the decreasing order of their rate of electrophilic aromatic nitration with a mixture of HNO ₃ and H ₂ SO ₄ : (I) (II) (III)

Options

  1. A(I) > (III) > (II)
  2. B(II) > (III) > (I)
  3. C(I) > (II) > (III)
  4. D(III) > (I) > (II)

Correct answer

A. (I) > (III) > (II)

Step-by-step solution

The rate of electrophilic aromatic substitution (such as nitration) depends on the electron density of the benzene ring. Electron-donating groups activate the ring and increase the rate, while electron-withdrawing groups deactivate the ring and decrease the rate. Let us analyze the substituent groups in the given compounds: 1. In compound (I), the - OCH ₃ group is strongly activating due to its strong +M (mesomeric) effect, which significantly increases the electron density on the ring. 2. In compound (III), the -

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