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Which of the following is the most acidic?(a) Benzoic acid(b) o-Toluic acid(c) m-Toluic acid(d) p-Toluic acidThis question was posed to me in semester exam.I'd like to ask this question from Carboxylic Acids Chemical Reactions topic in division Aldehydes, Ketones and Carboxylic Acids of Chemistry – Class 12

Answer»

Correct option is (b) o-Toluic acid

Easiest explanation: Although CH3 is an electron releasing group and should reduce the acidic character of acids by destabilizing it, the PRESENCE of CH3 group at ortho POSITION has a reverse effect and increases the acidic strength compared to benzoic acid. This is due to a combination of STEARIC and electronic FACTORS.



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