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Organic Chemistry Geometric Isomers Lab

  1. Sep 25, 2009 #1
    1. The problem statement, all variables and given/known data
    The experiment was changing dimethyl maleate into dimethyl fumerate, with the intent of being analogous to changing maleic acid into fumeric acid. In the experiment, we added 1 M Bromine in dimethylchlorine to our dimethyl fumerate, put the mixture in a hot water bath and next to a light for 10 minutes, then recrystallzied, filtered and got the melting point of the new substance.

    I'm having trouble with one of the post-lab questions: Could you start with dimethyl fumerate, do the same reaction (and under experimental conditions where dimethyl maleate could be recovered) and get dimethyl maleate?


    2. Relevant equations

    I can't find the reaction anywhere online and I don't know how to type it out, but basically what happens is that Bromine with a free radical reacts with one of the double-bonded carbons to break the double bond and allow for rotation. Once rotation occurs, Bromine breaks free and a double bond is formed again. Thus producing the geometric isomer.


    3. The attempt at a solution

    I'm thinking it's NOT possible to do the reverse direction. Dimethyl fumerate is the trans-isomer, and is therefore more stable. In equilibrium with a single bond, most of the molecules are going to be in trans. Therefore I think if you redid the experiment in the reverse direction, you might get some yield but not a respectable amount.

    I'm not really sure and don't have a whole lot of confidence in this answer, so I just wanted to bounce the idea off of someone else, see if it makes sense to them. Thanks :)
     
  2. jcsd
  3. Sep 29, 2009 #2

    chemisttree

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    Sounds good to me.
     
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