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Isomerization of dimethyl maleate to dimethyl fumarate

  1. Oct 6, 2008 #1
    1. The problem statement, all variables and given/known data

    Propose the mechanism through which dimethyl maleate convert to dimethyl fumarate.

    3. The attempt at a solution

    I think free radical bromination reaction plays a role here, but I'm not sure how. We first get two bromine radicals, one of which attacks the double bond in dimethyl maleate. What forms next? Does bromine ever get attached to the DMM?

    Thank you so much for your help!
  2. jcsd
  3. Oct 7, 2008 #2


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    Yes a Bromine intermediate with the Maleate is formed , the intermediate is able to rotate to convert to the Fumarate , Bromine dissociates giving you the Fumarate. Note that a mixture of isomers is the result since the formation of the Bromine intermediate is a reversible process.
  4. Oct 8, 2008 #3


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    We used to do it in the lab with acid and heat.
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