JEE Main levelSingle correct optionDifficulty 2 of 3o1186
Which acid is esterified most slowly by methanol with a catalytic strong acid under identical conditions?
A4-methylbenzoic acid
Bbenzoic acid
C2,6-dimethylbenzoic acid
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.