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JEE Main levelSingle correct optionDifficulty 2 of 3o1186

Which acid is esterified most slowly by methanol with a catalytic strong acid under identical conditions?

  1. A4-methylbenzoic acid
  2. Bbenzoic acid
  3. C2,6-dimethylbenzoic acid
  4. Dacetic acid

Answer: C

The tetrahedral intermediate in Fischer esterification is crowded. Two ortho methyl groups block attack at the carboxyl carbon (and twist the group out of conjugation), a large steric effect. The others have no ortho substituents.
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