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Homework Help: Solubility in Sulfuric Acid

  1. Jul 15, 2007 #1
    1. The problem statement, all variables and given/known data

    I just wanted to review what happens when methyl benzoate dissolves in sulfuric acid (the ionic species that arise). My workings/reasonings are below.

    2. Relevant equations

    See below.

    3. The attempt at a solution

    After the ester in placed in the acid, the O atom double bonded to the C (C=O group) is protonated by the acid.

    A series of resonance structures, such as





    Before the O atom is actually protonated, can the following be considered as one of the ions, aside from HSO4-, that are produced?

    Are there any other ions that I am missing from this reaction?

  2. jcsd
  3. Jul 22, 2007 #2


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    I think this question is not very clear. Are you talking about aqueous or anhydrous H2SO4? One or both of your resonance intermediates(?) is not right. For instance, the second one is clearly missing a (+) charge on the hydroxyl O-atom. I don't understand the final part of the question at all.

    I think the reaction with aq. H2SO4 could be a typical hydrolysis, making benzoic acid and methanol.
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