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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2217

Which of the following statements are correct?

  1. A2-Nitrobenzoic acid is a stronger acid than 4-nitrobenzoic acid
  2. BIn 2,6-dimethylbenzoic acid the group is twisted out of the plane of the ring
  3. C2-Methylbenzoic acid (pKa 3.91) is a stronger acid than 4-methylbenzoic acid (pKa 4.37)
  4. DSteric inhibition of resonance makes 2,6-dimethylbenzoic acid a weaker acid than benzoic acid

Answer: A, B, C

The ortho nitro group has a stronger effect than the para (pKa 2.17 against 3.44), so (A) is correct. Two ortho methyl groups twist the carboxyl group out of plane (B). The pKa values given show (C) is correct. The twist makes the acid stronger (pKa 3.25 against 4.20), so (D) is wrong.
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