3. Acids and Bases
Ranking Acidity
5:24 minutes
Problem 18-87c
Textbook Question
Textbook QuestionThe pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below:
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The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities.
NH2: meta > para > ortho
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