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Explain the observation that attempted Fischer esterification of $2,4,6$ -trimethylbenzoic acid with methanol and HCl is unsuccessful. No ester is obtained, and the...

Question

Explain the observation that attempted Fischer esterification of $2,4,6$ -trimethylbenzoic acid with methanol and HCl is unsuccessful. No ester is obtained, and the acid is recovered unchanged. What alternative method of esterification might be successful?

Explain the observation that attempted Fischer esterification of $2,4,6$ -trimethylbenzoic acid with methanol and HCl is unsuccessful. No ester is obtained, and the acid is recovered unchanged. What alternative method of esterification might be successful?



Answers

Propose a stepwise mechanism for the following reaction of a $\beta$-keto ester. Suggest a reason why this rearrangement reaction occurs.

We know we no, for a reaction have to be favorable. Their God s is close to positive where Delta s equals to us. Product minus s reactant. Okay, No. For first reactions. Doctor s is supposed to zero of here's and off the Essenes and the number off products are same. But for second reaction, no Delta Ass is better than zero is here one reactant. Okay. Okay. When they didn't give toe products, which makes this reaction highly and tropically favor this mhm. Hence increase the rate. The rate off reactions, then the first year.

This is the answer to Chapter 22. Problem number 66 from the Smith Organic Chemistry textbook On this problem is asking us to look at each of four Esther's and determine how these esters could be made by Fisher. A stare ification. So remember, Fisher s terrifically ation is treating a carb oxalic acid with an alcohol with some acid. And we get in Esther as a result. And so I've drawn a line in red through each of the oxygen's, um, each of these Esther Oxygen's. And basically you can just break the molecule in into two at that red line, and that will tell you you're starting materials. So for a, um, all right, so for a, uh, if we work, you break molecule at that red line that I've drawn, Um, and so remember, if you if you do treat it that way, breaking it at that red line, that oxygen goes to each of the starting materials. So you have a carb oxalic acid here, and then you have an alcohol. Uh, you have an alcohol in your other piece, so go 12 and so we just follow that form for the rest of molecules in this problem. So for B, uh, if we break our molecule into two pieces at that line, we have the alcohol here, and then the other piece would be our car box, so it gas it more. All right, there we go. And I'm just going toe rather than redraw, the fennel rang. I'm just going to abbreviate it with Ph. So there we go. That's the answer to beef for C will follow the same pattern. So here we have our car box sill like acid. And then our other piece eyes going to be, uh, the alcohol 23 All right. And then he's gonna be exactly the same way. So we have the left piece. Here will be our alcohol. So put Theo age there, and then the right piece will be our car box l a gas it. All right. There we go. And so this is the answer to Chapter 22. Problem number 66

Arise this question as us. What is given example offer the best information reaction. I would say the most common Esther would probably see is either estate. And that is the reaction. The three ah, acidic asset. And it isn't all. And so you eliminate water and you will found either our state. So how can this kind of reaction be extended to form a polymer? So imagine if you have an eye as it Ah, let's say something like this and react with denial. Um, this whoa, propagate, Connect together and farm a polymer or look like this, you and then another acid and alcohol and keep going like that.

Let's name the car broke. Cilic acid necessary to complete the Esther s terrific ation. The carb oxalic acid is too laurel Propane, OIC acid.


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