The p Ka values of a few ortho-, meta-, and para-substituted benzoic acids are shown

Chapter 19, Problem 88

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The p Ka values of a few ortho-, meta-, and para-substituted benzoic acids are shown here: COOH Cl NO2 COOH COOH Cl COOH Cl COOH NO2 pKa = 2.94 p pKa = 3.83 pKa = 3.99 Ka = 2.17 COOH NO2 pK pKa = 3.44 a = 3.49 NH2 COOH COOH NH2 COOH NH2 pKa = 4.95 pKa = 4.73 pKa = 4.89 The relative p Ka 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. a. Cl: ortho 7 meta 7 para b. NO 2 : ortho 7 para 7 meta c. NH 2 : meta 7 para 7 ortho

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