Nitro groups have a large acid-strengthening effect on phenols. The p K a of 4-nitrophenol is 7.15,

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Nitro groups have a large acid-strengthening effect on phenols. The pKa of 4-nitrophenol  is 7.15, whereas that of phenol is 9.89, a factor of almost 1000. Account for the greater acidity of 4-nitrophenol relative to phenol on the basis of resonance and inductive effects. Your answer will help explain why 2,4,6-trinitrophenol (also called picric acid) is so exceptionally acidic (pKa = 0.38) that it is more acidic than acetic acid (pKa = 4.76).

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Organic Chemistry

ISBN: 978-1118875766

12th Edition

Authors: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder

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