Confusing MCAT Organic Chemistry Question

[O-Block Uchiha]

So I'm taking a quest bank and one of the questions read: Which of the following reactions will produce butanone?
The answer: 3-oxopentanoic acid + heat.

Can someone please explain this reaction to me?! Thank you in advance.

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[deleted853480]

It just does. The heat cause a CO2 to leave the molecule and we get the desired product.

 

[TheBiologist]

look up decarboxylation mechanism

 

[aldol16]

The carboxylic acid decarboxylates upon addition of heat. Basically, the CO2 comes off as you form an enolate, which can then get protonated by the media (keto-enol tautomerism) to give you butanone.

Whenever you have a ketone beta to a carboxylic acid, you can usually get it to decarboxylate because formation of the enolate is fairly facile.

 

[O-Block Uchiha]

look up decarboxylation mechanism

Thanks, the video helped