Decarboxylation Explained, Reaction and Mechanism

joechem.io/vid... for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link)
Worksheet: worksheets.joec...
Worksheet Solution: worksheets.joec...
Worksheet Video Solution: joechem.io/vid...
Study Guide: (To be created, Joe's working on it!)
In this video, we tackle decarboxylation. This commonly pops up in complete the reaction questions, and it's TRULY not that bad, which means easy points on exams for us.
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[@PunmasterSTP]

1,3-dicarbonyl? More like "Wonderful videos, and since they're free it's a steal!"
This stuff will also never stop being COOl 👍

[@nandanabalakrishnan7888]

Well explained thank u sir🙂

[@myatminsoe9282]

Thank you for helping me out with this mechanisms.

[@sabidahsansami6603]

Thank you very much!!!!!

[@MayankTKD_]

Explained very well ❤❤

[@miramsl8795]

thank you 😊

[@LeylaIbrahimlichem]

Thanks bro

[@jOeCHEM]

Yw bro

[@macmackay2179]

can NaOH act as a base and a nucleophile, in the first problem how do we know it doesn't take a hydrogen but instead acts as a nucleophile?

[@jOeCHEM]

Hey, Mac! That's a good question. I agree that this first question I've posed is a bit multi-faceted, but all that is really happening here is Saponification, and addition-elimination mechanism where the -OR group of the ester is kicked off in favor of creating a carboxlic acid/caboxylate. Then, with the H2SO4, H20, and heat (delta) step, that signals that a decarboxylation is going to happen.
But, to answer your question: does an acid base reaction between the alpha hydrogen in between the carbonyls and hydroxide happen? It probably does; however, with the reagents posed here, when you see Acid + Heat and you have a 1,3 dicarbonyl situation (where one of those carbonyls is a carboxylic acid), that's your signal that a decarboxylation is going to happen. So that being your second step helps inform you that the first step is a saponification to transform your ester into a carboxylic acid/carboxylate to then in turn perform the decarboxylation.
Let me know if that helps or not, and thanks for watching!

[@macmackay2179]

@@jOeCHEM thank you! love your videos, they help a lot

[@jOeCHEM]

@@macmackay2179 I really appreciate that Mac! If you're looking for additional/guided practice, check out the videos on my actual website (same videos on my YT channel), but there you'll find linked worksheets + written solutions paired with a video explanation of the worksheet solutions.