Concept: Concept: General Reaction2m
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.
Concept: Concept: General Mechanism3m
Provide the reagents necessary and the mechanism to complete this transformation.
Show your understanding of the reaction given below by showing the full arrow pushing mechanism, including ALL RESONANCE FORMS and predicting the products.
Complete the mechanism for the following acid catalyzed ester hydrolysis reaction. Be sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges, and all the products for each step. IF A NEW CHIRAL CENTER IS CREATED IN AN INTERMEDIATE OR THE PRODUCTS, MARK IT WITH AN ASTERISK AND LABEL AS "RACEMIC" IF RELEVANT. IN THE BOX BY EACH SET OF ARROWS, WRITE WHICH OF THE 4 MECHANISTIC ELEMENTS IS INDICATED IN EACH STEP OF YOUR MECHANISM (For example, "Add a proton").
Draw a reasonable mechanism for the reaction below.