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Chemistry · L4 · Why carboxylic acids are stronger acids than alcohols

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Resonance delocalization in the carboxylate ion versus the localized negative charge on an alkoxide — the source of the ~10¹¹-fold acidity gap.

by @openstemUpdated Chemistry
Carboxylic acidR-COOHCarboxylate ionR-COO⁻(resonance-delocalizedover 2 equivalent C-O bonds)AlcoholR-OHAlkoxide ionR-O⁻(charge localizedon one oxygen)More stable anion→ stronger acidLess stable anion→ weaker acidloses H+ (pKa ~ 4-5)loses H+ (pKa ~ 16-18)

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