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Topic: What is the major product to this reactant when heat is added?  (Read 6333 times)

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Offline a confused chiral girl

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What is the major product to this reactant when heat is added?
« on: December 02, 2006, 04:17:24 AM »
I have tried this question, but it does not look right to me somehow. I don't think the OH will get reduced to H on the end, but I don't know how else I can predict it. thanks!!

Offline Alberto_Kravina

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Re: What is the major product to this reactant when heat is added?
« Reply #1 on: December 02, 2006, 04:23:52 AM »
It is impossible to reduce OH to H just so simply. you could dehydrate the CH2-CH2-OH group to CH=CH2 and then hydrogenate the double bond to single bond (i.e. with nascent hydrogen)
« Last Edit: December 03, 2006, 04:24:19 AM by Alberto_Kravina »

Offline a confused chiral girl

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Re: What is the major product to this reactant when heat is added?
« Reply #2 on: December 02, 2006, 04:25:35 AM »
sorry!! I mean...the product that is drawn is just my guess. I am looking for the product when heat is added to that reactant. So, totally ignore that product drawn as it is just my "guess'.

Offline Albert

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Re: What is the major product to this reactant when heat is added?
« Reply #3 on: December 02, 2006, 07:27:54 AM »
Ever heard of decarboxylation?

Offline taurean

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Re: What is the major product to this reactant when heat is added?
« Reply #4 on: December 02, 2006, 11:30:34 AM »
Ph-CO-CH3 is the answer.  Beta-keto carboxylic acids undergo decarboxylation (-CO2) when heat is added, to give the corresponding ketone as a product.

Offline Albert

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Re: What is the major product to this reactant when heat is added?
« Reply #5 on: December 02, 2006, 05:04:33 PM »
Ok, now that taurean has told you the answer, check out the mechanism. I hope it'll help you to understand (and appreciate) this wonderful reaction.  ;)
« Last Edit: December 03, 2006, 06:22:34 AM by Albert »

Offline a confused chiral girl

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Re: What is the major product to this reactant when heat is added?
« Reply #6 on: December 03, 2006, 03:29:38 AM »
thank you so much. I studied the mechanism (did you draw it by the way? or did you find it on the internet?  :D ) and I understand how the electron movements will give those products. But just by looking at the reactant there, I would have never ever knew this is decarboxylation reactant.
The answer that Taurean said is different from yours though...he said it's Ph-CO-CH3 and the reaction mechanism you posted is CH3-CO-CH3...so which one is correct?

Offline Albert

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Re: What is the major product to this reactant when heat is added?
« Reply #7 on: December 03, 2006, 06:12:14 AM »

The answer that Taurean said is different from yours though...he said it's Ph-CO-CH3 and the reaction mechanism you posted is CH3-CO-CH3...so which one is correct?

Looking at the picture I drew, paying attention to the fact I wrote R (neither Ph nor any other partucular group), can you see that, while tauteran tells the answer for your specific question, I gave you a general one, to help you deal with this kind of reactions in future?

EDIT: I've modified the picture: it's now better-looking and more useful than before.
« Last Edit: December 03, 2006, 06:24:00 AM by Albert »

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