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JEE Main levelSingle correct optionDifficulty 2 of 3g2012

Which of the following is the weakest acid?

  1. A3-nitrobenzoic acid
  2. B4-aminobenzoic acid
  3. C4-nitrobenzoic acid
  4. D3,5-dinitrobenzoic acid

Answer: B

The amino group at the para position donates electrons by +M effect, which destabilises the benzoate ion (pKa about 4.85). Each nitro-substituted acid has the anion stabilised by -I (and -M at para), giving pKa values of 3.5 or lower (3,5-dinitro about 2.8). So 4-aminobenzoic acid is the weakest.
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