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Topic: Carbonyl (cumulene) reactions  (Read 1580 times)

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Offline Anthasci

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Carbonyl (cumulene) reactions
« on: January 17, 2013, 03:43:23 PM »
I have a question regarding this specific reaction, I apologize for the puny ms paint picture, but I don't have any software on this computer here. Well, the question is basically written within the picture. Why isn't CO2 eliminated here, contrary to this reaction, for example:

Ph-N=C=O + H2O = Ph-NH2 + CO2

I can't wrap my head around it and having -Ph in both cases on the C-atom isn't helpful either. Could anyone shed some light on this for me, please?

Thanks

Offline Dan

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Re: Carbonyl (cumulene) reactions
« Reply #1 on: January 17, 2013, 04:19:08 PM »
If you draw the mechanism for decarboxylation of the carbamic acid and compare it to a mechanism for your proposed decarboxylation, you should see why the former is much easier.
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Offline Anthasci

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Re: Carbonyl (cumulene) reactions
« Reply #2 on: January 17, 2013, 04:26:18 PM »
I may have some ideas. In the case of carbamic acid, the Nitrogen atom has a lone pair, which can attract the carboxylic proton? It is also more electronegative than the C-atom, in regard to the 2,2-diphenylethanoic acid

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