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ion and an alcohol. Water is often used as a solvent, but the presence of water is not necessary; alcohols may also be used as solvents, with dissolved hydroxide ion performing hydrolysis.
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Rosini, Goffredo; Confalonieri, Giovanni; Marotta, Emanuela; Rama, Franco; Righi, Paolo (1997). "PREPARATION OF BICYCLOHEPT-3-EN-6-ONES: 1,4-DIMETHYLBICYCLOHEPT-3-EN-6-ONE".
64:. Acid is only required in catalytic amounts, as in Fischer esterification, and an excess of water drives the equilibrium towards carboxylic acid and alcohol.
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is required in stochiometric amounts. Unlike acid-catalyzed ester hydrolysis, it is not an equilibrium reaction and proceeds to completion.
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ion attacks the carbonyl carbon to give a tetrahedral intermediate, which then expels an
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ion. The resulting carboxylic acid quickly protonates the alkoxide ion to give a
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197:(4th ed.). Pacific Grove, CA: Brooks/Cole Publishing Company. pp.
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The mechanism of acid-catalyzed hydrolysis of esters is the reverse of
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of esters is also known as saponification. A base such as
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100:In this example of alkaline hydrolysis of
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112:experiment to investigate the mechanism:
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143:(8th ed.). Pearson. p. 1010.
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56:Hydrolysis § Acidic hydrolysis
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68:Alkaline hydrolysis of esters
104:, the asterisk indicates an
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50:Acidic hydrolysis of esters
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176:10.15227/orgsyn.074.0158
139:Wade Jr., L. G. (2012).
189:McMurry, John (1996).
62:Fischer esterification
229:Reactions of esters
79:Alkaline hydrolysis
193:Organic Chemistry
167:Organic Syntheses
141:Organic Chemistry
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110:isotope labeling
102:ethyl propionate
83:sodium hydroxide
24:organic reaction
20:Ester hydrolysis
16:Organic reaction
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36:carboxylic acid
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150:978-0321768414
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74:Saponification
72:Main article:
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108:atom in an
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123:References
54:See also:
28:hydrolyzes
106:oxygen-18
87:Hydroxide
42:, and an
223:Category
91:alkoxide
199:820–821
44:alcohol
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26:which
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32:ester
203:ISBN
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172:doi
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