The order of the following compounds with respect to decreasing acidity is:

II > IV > I > III

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I > II > III > IV

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III > I > II > IV

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IV > III > I > II

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Solution

The correct option is C III > I > II > IV
Electron withdrawing group will increase acidity of phenol so, p-nitrophenol is not acidic because of combined effect of -If-R effects. Electron donating group decreases the acidity of phenol. Since $- {O C H}_{3}$ is $- I, + R$ group, $- {C H}_{3}$ is $+$ and has hyper-conjugation effect $f$ - $C l$ group has - $I$ and $+ R$ effect but $- I$ effect predominates. So, considering the above facts, the order of compounds is given as above.

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