Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 21, Problem 2PP

PRACTICE PROBLEM

If we examine Table 21.1, we see that phenols having electron-withdrawing groups (Cl─ or O2N─) attached to the benzene ring are more acidic than phenol itself. Account for this trend on the basis of resonance and inductive effects. Your answer should also explain the large acid-strengthening effect of nitro groups, an effect that makes 2,4,6-trinitrophenol (also called picric acid) so exceptionally acidic (pKa = 0.38) that it is more acidic than acetic acid (pKa = 4.76).

Chapter 21, Problem 2PP, PRACTICE PROBLEM If we examine Table 21.1, we see that phenols having electron-withdrawing groups

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