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JEE Main levelSingle correct optionDifficulty 2 of 3g2191

Benzoic acid has pKa , 2-nitrobenzoic acid and 4-nitrobenzoic acid in water. Which sequence correctly gives decreasing acid strength, and its main reason?

  1. A4-nitro 2-nitro benzoic; the ortho group is shielded by steric hindrance
  2. B2-nitro 4-nitro benzoic; the ortho substituent adds the ortho effect to its electron-withdrawing effect
  3. Cbenzoic 4-nitro 2-nitro; nitro groups donate electrons
  4. D2-nitro benzoic 4-nitro; the para nitro group is a donor by resonance

Answer: B

A lower pKa means a stronger acid, so the order is . The nitro group withdraws electrons in both positions. At the ortho position it also twists out of the ring plane and acts close to the acid group (ortho effect), giving the strongest acid.
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