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The relative acidic strengths of benzoic...

The relative acidic strengths of benzoic acid, o-toluic acid and p-toluic acid is of decreasing order:

A

p-toluic acid `gt` o-toluic acid `gt` benzoic acid

B

o-toluic acid `gt` p-toluic acid `gt` benzoic acid

C

p-toluic acid `gt` benzoic acid `gt` o-toluic acid

D

o-toluic acid `gt` benzoic acid `gt` p-toluic acid

Text Solution

Verified by Experts

The correct Answer is:
D
The methyl group at ortho and para – position destabilizes negative charge of corresponding carboxylate ion because of +I effect. In o – toluic acid, steric hindrance results in the carboxyl group being out of the plane of the aromatic ring. The carboxyl group being out of the plane inhibits +R effect of benzene. Hence o – toluic acid is even stronger than benzoic acid.
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