saponification

[MedGrl@2022]

I just want to make sure that I understand saponification.

Saponification is the base hydrolysis of any ester into a carboxylic ion and an alcohol, right? Can any of the alkai hydroxides be used, what about other hydroxides? In addition, the base MUST be a hydroxide group right? Because the hydroxide is the only base that is capable of hydrolysis?

Thank you for your help! 🙂

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[dudewheresmymd]

You've got it. Saponifcation can occur with any alkali base of hyroxide. (In fact in the soap industry, NaOH is used to make hard soaps whereas KOH is used to make soft soaps). The base is a hydroxide group because as you mentioned basic hydrolysis requires hydroxide to attack the electrophilic center expelling the alkoxy ester group which then goes on to deprotonate the acid intermediate forming carboxylate and an alcohol.


If saponification (3 equivalents of NaOH) are added to a fat (triacyl glycerol) you form glycerol and soap (the long chain sodium carboxylate salts).