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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2230

Four benzoic acids are shown beside the options (the drawn compound is benzoic acid, pKa 4.20). Select ALL the structures that are stronger acids than the drawn compound.

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B, C, D

p-Nitrobenzoic acid (3.44) is stronger by -I and -M. m-Chlorobenzoic acid (3.83) is stronger by -I. o-Toluic acid (3.91) is stronger through the ortho effect: the methyl group forces COOH out of the ring plane, so the +R-like conjugation of the ring with COOH is lost and the acid is strengthened. p-Toluic acid (4.34) is weaker because of +I and hyperconjugation.
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