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Question 13.1: Predicting the Relative Acidity of a Substituted Phenol Is p...

Predicting the Relative Acidity of a Substituted Phenol

Is p-hydroxybenzaldehyde more acidic or less acidic than phenol?

Strategy
Identify the substituent on the aromatic ring, and decide whether it is electrondonating or electron-withdrawing. Electron-withdrawing substituents make the phenol more acidic by stabilizing the phenoxide anion, and electrondonating substituents make the phenol less acidic by destabilizing the anion.

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We saw in Section 9.8 that a carbonyl group is electron-withdrawing. Thus, p-hydroxybenzaldehyde (pK_{a} = 7.89) is more acidic than phenol (pK_{a} = 9.89).

 

13.1

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