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Topic: cleavage of beta-dicarbonyl to acid  (Read 3012 times)

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Offline gkasparis

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cleavage of beta-dicarbonyl to acid
« on: January 31, 2013, 01:18:22 AM »
i have to find a mechanism for the cleavage of 2-acetyl cyclohexanone with strong alkali to produce 7-oxooctanoic acid. i cant get my mind around this since there is an acidic proton in between the two (which i didn't think that it can be removed by alkali but i cant find another start). please give me a clue to get me going
thanks
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Offline Dan

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Re: cleavage of beta-dicarbonyl to acid
« Reply #1 on: January 31, 2013, 02:55:09 AM »
The acidic proton can be removed, an equilibrium will be established, but the anion is not productive.

Think about alternative ways in which the hydroxide can react - it is a base, but also a                      
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Offline gkasparis

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Re: cleavage of beta-dicarbonyl to acid
« Reply #2 on: January 31, 2013, 11:50:29 AM »
oh silly me... i used it as a nucleophile, formed the enolate and get a proton from water to generate a hydroxide again, if I'm correct!
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Offline Dan

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Re: cleavage of beta-dicarbonyl to acid
« Reply #3 on: January 31, 2013, 12:34:16 PM »
Sounds like that's right, though without a scheme it's hard to be sure.

This reaction is called a reverse Claisen (or retro Claisen) - it is the reverse of the Claisen condensation.
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