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Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

20. Carboxylic Acid Derivatives:NAS

Acid-Catalyzed Ester Hydrolysis

Are you having deja vu? You should be! We are learning a mechanism that is the exact opposite of Fischer Esterification.That means instead of going from a Carboxylic Acid to an Ester, we are hydrolyzing an Ester to a Carboxylic Acid

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General Reaction

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Let's talk about a reaction called acid catalyzed. Esther. Hydraulic. Sis. So, guys, acid catalyzed Esther. Hydraulic sis is literally just the reverse of Fisher s terrific ation. Okay, so it's literally just the reverse reaction off producing an Esther. You could then hydrolyzed that Esther back to a carbon slick acid. So the general reaction would be that you have your Esther, but you react your Esther in an acquis solution with acid, and you're gonna hide relies that, um, you're gonna hide relates that Esther to a car. Oxalic acid. Okay, So also, guys, if you recall the three rules of NES, this would be rule number three, the car with gas and conversion that says that pretty much any Carlos look as a derivative in combination with water, acid or base could turn into a car. Looks like acid. Okay, so now what I want to do is go through the mechanism for this. And by the way, guys, I already told you it's the exact opposite of Fisher as certification. So if you literally wanted to go to the Fisher as certification video and draw out every arrow backwards, every nuclear file backwards, you would get the mechanism. But I know that you guys are gonna complain if I don't draw the reverse reaction. So let's go ahead and do that. Now I'm gonna show you guys exactly how to draw the reverse of fish are, sir vacation?
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General Mechanism

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All right, So let's start off with our Esther, okay? And I'm gonna go ahead and use H 30 plus as my acid. Okay, so it's gonna be the first step, okay? It's gonna be pro nation. You got it. Mhm. That's going to give me a compound that looks like this positive charge. What's my next step? Resonate. So it's resonate that's going to give me a positive here, show my president structure, and this is a great time to nuclear physically attack. So I'm gonna get water, and my water is going toe attack and I'm gonna form a molecule. Wait, Let me drop my equilibrium, Arrows! I'm gonna form a molecule that looks like this. Oh, each of the top Oh, are on the side and water at the bottom. Can you guess what the next step is gonna be? So, guys, what are we trying to get rid of? We're trying to get rid of the O. R. Which means that I want to do a proton transfer specifically to the O. R. This time. Okay, Every saying. Well, Johnny, how do you know that it doesn't go to the O. H Well, because then that would be the forward mechanism. Okay, so I'm just trying to go backwards here, so I'm trying to get rid of the O. R. So this o r grabs that h and turns into oh h r Positive. Okay, Now what happens is I eliminate I used the electrons from my oh, to kick out the O R. Oops, that's not gonna work. And I now have a structure that looks like this. Oh, h positive are Ohh. And now I use what to deep Rotimi water to regenerate my acid. Okay, guys. So if anything, this serves as extra practice for you for the Fisher. A certification mechanism, because it is that mechanism. Okay, Plus my age three or plus and plus my alcohol, Right, Because I generated one equivalent of alcohol that I lost. Okay, So, guys, that's really it. Let's move on to the next video.

Mechanism:

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