Esterification and saponification
Carboxylic Acids and Derivatives · Chemistry
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Why does saponification go to completion but esterification needs excess reactant? Step 1: Esterification is reversible equilibrium (K ~4). Step 2: Remove water or use excess alcohol to drive it right (Le Chatelier). Step 3: Saponification: OH⁻ attacks ester → carboxylate anion RCOO⁻. Step 4: RCOO⁻ won't react back (negative charge repels) → irreversible! Product stability decides reversibility.