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Arrange the following compounds in the correct decreasing order of acidic strength. I: p-hydroxybenzonitrile II: 3-methyl-4-hydroxybenzonitrile III: 3,5-dimethyl-4-hydroxybenzonitrile IV: o-methylbenzoic acid

1. I > III > II > IV
2. II > III > I > IV
3. I > II > III > IV
4. IV > I > II > III

Correct answer: IV > I > II > III

Solution

IV (o-methylbenzoic acid) is a carboxylic acid and is most acidic. Among the three phenols, I has -CN directly increasing acidity; II has one electron-donating methyl reducing acidity relative to I; III has two methyls making it least acidic. Hence IV > I > II > III.

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