Practice Problem 17.1 Is p-cyanophenol more acidic or less acidic than phenol?
strategy: Identify the substituent on the aromatic ring, and decide whether it is electron-donating or electron-withdrawing. Electron-withdrwing substituents make the phenol more acidic by stabilizing the phenoxide anion, and electron-donating substituents mack the phenol less acidic.
Solution:We saw in Section 16.6 that a cyano group is electron-withdrawing. Thus, p-cyanophenol is more acidic (pKa=7.97) than phenol (pKa=9.89).