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СООН СООН СООН СООН СООН СООН Cl NO2 CI `NO2 ÑO2 pK = 3.44 pк, — 2.94 pK =3.83 pк, — 3.99 pк, — 2.17 pK = 3.49 СООН СООН СООН „NH2 `NH2 NH2 pК, 3 4.89 pк, — 4.95 pк, — 4.73

СООН СООН СООН СООН СООН СООН Cl NO2 CI `NO2 ÑO2 pK = 3.44 pк, — 2.94 pK =3.83 pк, — 3.99 pк, — 2.17 pK = 3.49 СООН СООН СООН „NH2 `NH2 NH2 pК, 3 4.89 pк, — 4.95 pк, — 4.73

Chemistry In Focus
Chemistry In Focus
7th Edition
ISBN:9781337399692
Author:Tro, Nivaldo J.
Publisher:Tro, Nivaldo J.
Chapter9: Energy For Today
Section: Chapter Questions
Problem 9E
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The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below:

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.
a. Cl: ortho 7 meta 7 para

b. NO2: ortho 7 para 7 meta

c. NH2: meta 7 para 7 ortho

СООН СООН СООН СООН СООН СООН Cl NO2 CI `NO2 ÑO2 pK = 3.44 pк, — 2.94 pK =3.83 pк, — 3.99 pк, — 2.17 pK = 3.49 СООН СООН СООН „NH2 `NH2 NH2 pК, 3 4.89 pк, — 4.95 pк, — 4.73
Transcribed Image Text:СООН СООН СООН СООН СООН СООН Cl NO2 CI `NO2 ÑO2 pK = 3.44 pк, — 2.94 pK =3.83 pк, — 3.99 pк, — 2.17 pK = 3.49 СООН СООН СООН „NH2 `NH2 NH2 pК, 3 4.89 pк, — 4.95 pк, — 4.73
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