Basic hydrolysis of esters (saponification)

by James

Description: Esters can be converted to carboxylic acids through treatment with strong base.
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{ 4 comments… read them below or add one }

Lynne Dusseau March 16, 2015 at 5:03 pm

Is this really not an equilibrium? Because it says it is in my textbook for mechanism of Saponification of esters


James March 17, 2015 at 10:37 pm

It’s not an equilibrium if the ester is being treated with NaOH, no. Once the carboxylic acid forms, it will be deprotonated to give the carboxylate and it stays there.

Now, if instead of NaOH, an alkoxide is used (like NaOCH3 or NaOEt) THEN the reaction will be in equilibrium between two esters. That’s called, “transesterification” which is slightly different : – )


Yasmin weiss June 19, 2015 at 6:42 pm

I’m a little confused with the third example since it started with 5 carbons and ended with 6 carbons


James September 4, 2015 at 4:57 pm

Fixed, thank you!


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