Organic Chemistry Geometric Isomers Lab

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SUMMARY

The discussion centers on the organic chemistry experiment involving the transformation of dimethyl maleate into dimethyl fumerate using 1 M Bromine in dimethylchlorine. The experiment aims to illustrate the conversion analogous to maleic acid to fumaric acid. The participant questions whether it is feasible to reverse the reaction to obtain dimethyl maleate from dimethyl fumerate, concluding that due to the stability of the trans-isomer (dimethyl fumerate), the reverse reaction would yield minimal results. The participant expresses uncertainty about the reaction mechanism but identifies the role of Bromine in facilitating geometric isomer formation.

PREREQUISITES
  • Understanding of organic reaction mechanisms, specifically free radical reactions.
  • Familiarity with geometric isomers and their stability.
  • Knowledge of recrystallization techniques in organic chemistry.
  • Experience with melting point determination of organic compounds.
NEXT STEPS
  • Research the mechanism of free radical bromination in organic compounds.
  • Study the stability differences between cis and trans isomers in organic chemistry.
  • Explore recrystallization methods for purifying organic compounds.
  • Learn about the thermodynamics of equilibrium in chemical reactions.
USEFUL FOR

Organic chemistry students, laboratory technicians, and researchers interested in reaction mechanisms and geometric isomerism in organic compounds.

ohgeecsea
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Homework Statement


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?

Homework 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.

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 :)
 
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Sounds good to me.
 

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