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Question

The relative acidic strengths of benzoic acid, o-toluic acid, and p-toluic acid in decreasing order can be given as:

A
p-toluic acid > o-toluic acid > benzoic acid
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B
o-toluic acid > p-toluic acid > benzoic acid
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C
p-toluic acid > benzoic acid > o-toluic acid
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D
o-toluic acid > benzoic acid > p-toluic acid
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Solution

The correct option is D o-toluic acid > benzoic acid > p-toluic acid
The decreasing order of the relative acidic strengths of benzoic acid, o-toluic acid and p-toluic acid is:
o-toluic acid > benzoic acid > p-toluic acid.
In a case of p-toluic acid, a methyl group is an electron releasing substituent and intensifies the negative charge of the carboxylate anion and destabilizes it and decreases the acidity. Hence, p-toluic acid is less acidic than benzoic acid.
The ortho-isomer of every substituted benzoic acid is the strongest acid due to ortho effect.

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