Resonance and mesomeric effect
General Organic Chemistry (GOC) · Chemistry
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Why is phenol (pKa ~10) more acidic than ethanol (pKa ~16)? Step 1: Acidity depends on anion stability after H⁺ leaves. Step 2: Phenoxide: negative charge delocalizes into benzene ring (resonance structures). Step 3: Ethoxide: charge stuck on oxygen, only +I destabilizes. Step 4: Resonance stabilization → phenol gives up H⁺ a million times more readily!