Formation of Carboxylic Acids from Acyl Chlorides

by James

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

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

Examples: 

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.

[/private_ReactionGuide]

{ 1 comment… read it below or add one }

Melissa Hoaglund

Could this also be done with NaOH?

Reply

Leave a Comment