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Thread: Grignard Reaction

  1. #1 Grignard Reaction 
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    Oct 2013
    hello everyone

    i have a lab, they ask me: in the reaction between an ester and the Grignard reagent (organomagnesium halide), we obtain the product of two nucleophilic additions, even if we use one equivalent of this reagent, so why?

    please help, i understand the mecanism of the reaction , but i can't explain why we have two nucleophilic additions in the same time?

    the reaction:
    Ethyl 2-methyl-1,3-dioxolane-2-acetate + phMgBr -----------> 2-(2-Methyl-1,3-dioxolan-2-yl)-1,1-diphenylethanol

    the solvent is Et2O
    and we hydrolyse with H3O+ (cold water)

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  3. #2  
    KJW is offline
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    Jun 2013
    As I understand it, you are adding the ester to the Grignard reagent and therefore the Grignard reagent is in excess during the addition. Therefore, the intermediate ketone that is formed will react with this excess Grignard reagent. Also, the intermediate ketone reacts more rapidly than the starting ester, so the ketone that is formed will react preferentially to the starting ester.

    There are no paradoxes in relativity, just people's misunderstandings of it.
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