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3. Acids and Bases - Part 2 of 2
3. Acids and Bases / Ranking Acidity / Problem 9

A negative charge on an adjacent carbon atom can be stabilized by a nitrile group (-CN) through resonance. Of the three hydroxybenzonitrile derivatives shown below, one is only slightly more acidic than phenol, while the other two are much more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to explain why two of the ions are unusually stable.

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