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2011 DAT Destroyer #172 OCHEM

Discussion in 'DAT Discussions' started by pandalove89, Aug 7, 2011.

  1. pandalove89

    7+ Year Member

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    Ehtylmagnesium chloride C2H5MgCl would not react with which of the following?
    a)methanol
    b)diethyl ether
    c)acetic acid
    d)methylamine
    e)propyne

    Since it is a grignard reagent (base) the solution says that we are looking for a basic reactant because we don't want the grignard reagent to react with an acid.

    So shouldn't it be d) ? I thought methylamine was a base. The answer is b).....which i thought was slightly acidic
     
  2. frances362002

    5+ Year Member

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    More accurately it should be that we don't want the grignard reagent to react with any thing that has an acidic H (or in a more general sense, a dissociable H). Only ether has no acidic H. Although methylamine is slightly basic, its pKa is still lower than hydrocarbons. So its H is still dissociable when it's faced with organometallic reagent.

     

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