6- Alkaline hydrolysis of esters
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9 Terms
What reagent is used for alkaline hydrolysis?
Dilute sodium hydroxide.
What conditions are used?
Heat under reflux.
What products are formed?
A carboxylate salt and an alcohol.
Write the reaction for methyl propanoate with NaOH.
CH₃CH₂CO₂CH₃ + NaOH → CH₃CH₂CO₂⁻Na⁺ + CH₃OH.
Is alkaline hydrolysis reversible?
No.
Why is alkaline hydrolysis not reversible?
The carboxylate ion formed is resistant to attack by weak nucleophiles such as alcohols.
Does alkaline hydrolysis go to completion?
Yes.
Why is excess NaOH used?
To ensure the ester is completely hydrolysed.
What is the carboxylic acid salt product?
The carboxylate salt/anionic form of the carboxylic acid.