A nitro group (NO2) effectively stabilizes a negative charge on an adjacent carbon atom

Chapter 10, Problem PROBLEM 10-9

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A nitro group \(\left(-\mathrm{NO}_{2}\right)\) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:

Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.

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