Acid-Catalyzed Ester Hydrolysis

Concept: Concept: General Reaction

Video Transcript

Let's talk about a reaction called acid-catalyzed ester hydrolysis. Acid-catalyzed ester hydrolysis is literally just the reverse of Fischer esterification. It's literally just the reverse reaction of producing an ester. You could then hydrolyze that ester back to a carboxylic acid. The general reaction would be that you have your ester but you react your ester in an aqueous solution with acid. You’re going to hydrolyze that ester to a carboxylic acid. Also if you recall, the three rules of NAS. This would be rule number three. The carboxylic acid conversion that says that pretty much carboxylic acid derivative in combination with water or acid or base could turn into a carboxylic acid. Now what I want to do is go through the mechanism for this. By the way, I already told you it’s the exact opposite of Fischer esterification. If you literally wanted to go to the Fisher esterification video and draw out every arrow backwards, every nucleophile backwards, you would get the mechanism. But I know that you guys are going to complain if I don't draw the reverse reaction. Let's go ahead and do that now. I’m going to show you guys exactly how to draw the reverse of Fisher esterification.