Octet / Reactions
Saponification (Base-Catalyzed Ester Hydrolysis)
Saponification (Base-Catalyzed Ester Hydrolysis) (Carbonyl.) Converts CC(=O)OCC to CC(=O)[O-].CCO using NaOH, KOH. Conditions: Aqueous base, reflux.
Carbonyl
Reaction details
Name
Saponification (Base-Catalyzed Ester Hydrolysis)
Type
Carbonyl
Starting Material
CC(=O)OCC
Product
CC(=O)[O-].CCO
Reagents
NaOH
KOH
Conditions
Aqueous base, reflux
Mechanism
- Smiles
CC(=O)OCC
- Description
Ethyl acetate
- Smiles
CC(=O)OCC
- Description
OH⁻ attacks carbonyl directly
- Smiles
CC(=O)[O-].CCO
- Description
Acetate + ethanol (irreversible - makes stable carboxylate)
Tips
IRREVERSIBLE (product is stable carboxylate)
Used to make soap from fats (saponification)
Faster than acid hydrolysis
Product is carboxylate salt, not free acid
Related Reactions
ester-hydrolysis-acid
fischer-esterification
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