21.7 Malonic Ester Synthesis and Acetoacetic Ester Synthesis | Organic Chemistry
Chad provides a comprehensive lesson on the Malonic Ester Synthesis and the Acetoacetic Ester Synthesis. Both of these are examples of a 'template synthesis' in which a certain type of product is formed with variation on the attached alkyl groups depending on which reagents are specifically used. The lesson begins with a description of Beta-Decarboxylation as this is a component in both of these template syntheses including the mechanism of the key step. Next, the Malonic Ester Synthesis is shown to produce carboxylic acids which vary only in which alkyl group(s) is/are attached to the alpha carbon. Finally, the Acetoacetic Ester Synthesis is shown to produce methyl ketones which vary only in which alkyl group(s) is/are attached to the alpha carbon.
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00:00 Lesson Introduction
01:21 Beta-Decarboxylation
05:39 Malonic Ester Synthesis
12:45 Acetoacetic Ester Synthesis
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Пікірлер: 17
This is the best explanation and comparison of these processes that I've found, as usual. Thank you, Chad!
@ChadsPrep
3 ай бұрын
You're welcome and Thank You!
your explanations are always through and incredibly comprehensive!!
@ChadsPrep
2 жыл бұрын
Glad you think so - Thanks!
This was amazingly helpful in comparing/contrasting these processes - thank you!!
@ChadsPrep
3 жыл бұрын
You're welcome, Amanda - glad it helped!
Thank you for making this make sense to me! SOOO helpful!
@ChadsPrep
2 жыл бұрын
You're welcome, SS!
thank u so much sir, you are honestly the best teacher out there..
@ChadsPrep
Жыл бұрын
Thanks! Great to have you here :)
For the malonic ester synthesis, what is the in-depth reason why we need to use NaOEt? If we hydrolyze the esters, does it matter if they got converted to O=C-OMe esters using NaOMe?
Great work, Chad!
@ChadsPrep
2 жыл бұрын
Thank you, Ben!
Awesome vid and so thankful that this is available. Just a quick question - when at 2:30 we say that the carboxylic acid on the right is unstable - is it also fair to say that it's a strong acid (so reactive/unstable) as a result of the Beta carbonyl being electron withdrawing? Or is it specifically because of that kinda ring formation that gets made.
@ChadsPrep
6 ай бұрын
The lack of stability is referring to the fact that beta keto acids (with the C=O on the beta carbon) break down readily in heat in comparison to other carboxylic acids. The reason for this is that we form the cyclic concerted transition state as a result of the H being spatially close to the carbonyl as mentioned. You could think of the beta carbonyl as being withdrawing as the electrons are moving in that direction in the mechanism of the reaction, but it is a part of the bigger picture.
thank you for these videos
@ChadsPrep
Жыл бұрын
You are welcome!