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Formation of Carboxylic Acids from Acyl Chlorides

Description: Treatment of acid chlorides with water leads to formation of carboxylic acids. This is called “hydrolysis”.

Notes: It’s also possible to do this reaction with acid bromides and anhydrides.


Notes: See how in the first three examples we are converting acid chlorides to carboxylic acids.

Mechanism: In the first step, addition of water to the carbonyl carbon of the acid chloride (Step 1, arrows A and B) leads to a tetrahedral intermediate, which then eliminates chloride ion (Step 2, arrows C and D) followed by deprotonation (Step 3, arrows E and F) to give the neutral carboxylic acid.

Notes: It’s also reasonable to show a proton transfer happening before the elimination step, followed by deprotonation.