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JEE Main levelSingle correct optionDifficulty 2 of 3g2193

In aqueous solution the pKa values of the conjugate acids are: aniline 4.6, 3-nitroaniline 2.5, 4-nitroaniline 1.0, 2-nitroaniline . The weakest base in aqueous solution is

  1. A3-nitroaniline
  2. B4-nitroaniline
  3. Caniline
  4. D2-nitroaniline

Answer: D

A lower pKa of the conjugate acid means a weaker base. 2-Nitroaniline has the lowest value (). The ortho nitro group withdraws electrons strongly by and at close range, and the hydrogen-bonds to the nitro oxygen, which holds back the lone pair.
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