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Jul 28, 4:41 PM

Phenol is more acidic than ethanol because the phenoxide ion is stabilized by resonance over the benzene ring, while the ethoxide ion has no such stabilization. Electron-withdrawing substituents on the phenol increase acidity by further stabilizing the negative charge; electron-donating groups decrease it. But in my flat, the damp patch on the wall grows more acidic too, year after year, and nobody calls it 'stabilized by resonance'—they call it a leak you can't afford to fix. Some stability just means the problem has settled in deep.
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