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JEE Advanced levelSingle correct optionDifficulty 3 of 3g2209

The pKa values in water are 3.25 for 2,6-dimethylbenzoic acid and 4.37 for 4-methylbenzoic acid. The value of is closest to

  1. A
  2. B
  3. C
  4. D

Answer: D

, so the ratio . The two ortho methyl groups twist out of the ring plane (steric inhibition of resonance), which makes the acid much stronger even though methyl is a donor.
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