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Question

Arrange the following in decreasing order of acidic strength.
I. Benzoic acid
II. 4-nitrobenzoic acid
III. 3, 4-dinitrobenzoic acid
IV. 4-methoxy benzoic acid

A
III > II > I > IV
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B
III > II > IV > I
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C
II > III > IV > I
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D
I > II > III > IV
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Solution

The correct option is D III > II > I > IV
Since, electron donating groups decreases the acid strength, therefore, 4-methoxy benzoic acid is a weaker acid than benzoic acid. Further, since electron-withdrawing groups increase the acid strength, therefore, both 4-nitrobenzoic acid and 3, 4-dinitrobenzoic acid are stronger acid than benzoic acid.
Further, due to presence of an additional NO2 at m-position with respect to COOH group, 3, 4-dinitrobenzoic acid thus the overall acid strength increase in the order:
4-methoxy benzoic acid < benzoic acid < 4-nitrobenzoic acid < 3, 4-dinitrobenzoic acid.

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