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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1102

Arrange in decreasing order of acid strength: (I) 2,6-dimethylbenzoic acid, (II) 2-methylbenzoic acid, (III) benzoic acid, (IV) 4-methylbenzoic acid.

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

Answer: A

Ortho methyl groups twist the group out of the ring plane; two of them do it more effectively than one, and the acid becomes stronger. The para methyl group makes the acid weaker than benzoic acid by its electron-releasing effects. The pKa values are about 3.3, 3.9, 4.2 and 4.4, so I > II > III > IV.
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