Isomerization of dimethyl maleate to dimethyl fumarate

  • Thread starter Momentum09
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In summary, the conversion of dimethyl maleate to dimethyl fumarate involves a free radical bromination reaction, where a bromine intermediate is formed and able to rotate to convert to fumarate. This process results in a mixture of isomers and is often done in the lab with acid and heat.
  • #1
Momentum09
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Homework Statement



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

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!
 
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  • #2
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.
 
  • #3
We used to do it in the lab with acid and heat.
 

1. What is isomerization?

Isomerization is a chemical process in which a molecule is transformed into another molecule with the same molecular formula but a different arrangement of atoms.

2. Why is dimethyl maleate isomerized to dimethyl fumarate?

Dimethyl maleate is isomerized to dimethyl fumarate because the latter is more stable and has a lower energy state. This transformation also allows for the formation of a more desirable product for certain applications.

3. What conditions are needed for the isomerization of dimethyl maleate to dimethyl fumarate?

The isomerization of dimethyl maleate to dimethyl fumarate typically requires heat and the presence of a catalyst, such as an acid or a metal ion.

4. What are the potential uses of dimethyl fumarate?

Dimethyl fumarate has several potential uses, including as an intermediate in the production of pharmaceuticals, as a flavoring agent in food and beverages, and as a component in polymer materials.

5. What are the benefits of isomerization in the production of dimethyl fumarate?

Isomerization allows for the production of a more stable and desirable molecule, as well as potentially increasing the yield of the desired product. It also allows for the conversion of a less useful or unwanted molecule into a more useful one.

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