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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: connie_fhy on December 18, 2005, 08:00:10 AM

Title: question about dibenzalacetone
Post by: connie_fhy on December 18, 2005, 08:00:10 AM

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is the reaction above correct???
I don't know where the -OH groups should be...
Would anyone kindly answer my question??
thank you very much~~

Title: Re:question about dibenzalacetone
Post by: BelarusGirl on December 18, 2005, 11:27:35 AM

I'm not sure, but I think that if temperature is about 100C, then carbonyl may be oxidized into carboxyl to form 2 carboxylic acids. If temperature isn't high, then maybe simple hydroxylation takes place. But it seems to me that this product won't be stable.  :-\

Title: Re:question about dibenzalacetone
Post by: connie_fhy on December 19, 2005, 07:36:26 AM

Oh~thank you for answering me~~ :D

but I asked some laboratory technical staff this afternoon~~
and I got a possible answer~~

Title: Re:question about dibenzalacetone
Post by: movies on December 19, 2005, 12:27:23 PM

I think that starting material is usually called dibenzylideneacetone.

Title: Re:question about dibenzalacetone
Post by: BelarusGirl on December 19, 2005, 03:07:45 PM

connie_fhy, could you tell me whay is the answer? ???

Title: Re:question about dibenzalacetone
Post by: moussa on December 19, 2005, 04:47:37 PM

hi  
KMnO4 is a very strong oxidizing agent it hydrolyse your compound to two carboxilic acids rather than that you put.
this were correct if you were using Cr2O72- that is less oxidizing, you can undergo this oxidation by puting a temp. higher than that of  of evaporationketone and higher than that of alcohol and use distilation method. thus isolating your product
but with KMnO4 no isolation of intermediate is possible  you'll go directly to the final product carboxilic acid

Title: Re:question about dibenzalacetone
Post by: movies on December 20, 2005, 01:47:54 AM

You can sometimes isolate the diol product if you run the reaction at colder temperatures.  This process is used on industrial scale for dihydroxylation!

Title: Re:question about dibenzalacetone
Post by: moussa on December 20, 2005, 03:43:32 PM

well it is a new important information that i'll take in conisedration
 i thought it couldn't happen with KMnO4
thank