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    Does anyone know the mechanism to go from EAA (ethyl acetoacetate) to CH3CHOHCH2CH3?

    I've got a mechanism using EtO- initially to remove a proton from the central carbon atom and then Me-I to add a methyl group. But then I'm not sure in what steps, why and how the decarboxylation occurs and the carbonyl group turns into a hydroxy group.



    Thanks
    Dan
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    It's decarboxylation of a beta-ketoester, there's a nice explanation here http://www.chem.ucalgary.ca/courses/.../ch21-4-2.html
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    (Original post by Calian)
    It's decarboxylation of a beta-ketoester, there's a nice explanation here http://www.chem.ucalgary.ca/courses/.../ch21-4-2.html
    Thanks, so does the ch2ch3 on the end of the COO group not make any difference to the reaction mechanism then i.e. i don't have to remove this first?
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    Yes it would make a difference as the carboxylic acid proton has to be involved in the decarboxylation, so the ethyl group is removed first by acid (or base) catalysed hydrolysis of the ester. There's a mechanism for ester hydrolysis here http://www.chemguide.co.uk/physical/...hydrolyse.html tho I'm sure you already know it :P Hope this helped
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    (Original post by Calian)
    Yes it would make a difference as the carboxylic acid proton has to be involved in the decarboxylation, so the ethyl group is removed first by acid (or base) catalysed hydrolysis of the ester. There's a mechanism for ester hydrolysis here http://www.chemguide.co.uk/physical/...hydrolyse.html tho I'm sure you already know it :P Hope this helped
    Just worked it out before you posted but thanks, that mechanism helped to show I was doing it right. Thanks
 
 
 
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