3. Acids and Bases
Ranking Acidity
57PRACTICE PROBLEM
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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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.