Are Alkene Diastereomers Formed Equally in Carbocation Reactions?

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SUMMARY

The discussion centers on the formation of alkene diastereomers, specifically Maleic and Fumaric acids, during carbocation reactions. The experiment involved dissolving Maleic acid in hot water and mixing it with hydrochloric acid, leading to a mixture analyzed via thin-layer chromatography. The results indicated a product that was a mixture of both diastereomers, suggesting that neither is preferentially formed, as the concentrations were found to be similar after reaching equilibrium. The stability of Fumaric acid as a trans-isomer was also debated, with participants questioning the implications of carbocation stability on the final product ratios.

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MarcL
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Hey, so I did a lab on alkene Diastereomers ( I saw a similar thread but it wasn't really helpful... However I am guessing the same lab as me).

We initially had Maleic acid and dissolved it in hot water and mixed it with hydrochloric acid ( carbocation?).The question isn't so clear ( to me anyways). It stats "Will one of the alkene diastereomers [Fumeric and Maleic Acid] be formed preferentially from the carbcation?"


Wouldn't one of these two be formed anyway after the temporary carbocation is done? I would expect them to have be more stable? ( I might completely wrong with my logic).

And my experiment shown my unknown ( so the solution we got after the reflux reaction) to be "between" maleic acid and fumeric acid when we analyzed it through thin-layer chromatography. Would that mean that some molecules will be cis-isomers and others trans-isomers?

p.s sorry for the language; french and haven't done chem in a year ( was in math so I am refreshing my memory)

Thank you for your help
 
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It is about ratio of the products - preferentially means one of the acids will be present in larger amount than the other. If - after reaching equilibrium - concentrations are identical, there is no preference.
 
makes sense so if its half of the way to fumeric acid and maleic acid it would mean both are as stable as the other? However, theoritically, shouldn't fumeric be more stable as it is a trans-isomers? I was thinking this because the carboxyl groups are on the "opposite side" of each other. Sorry for my "dumbed" down logic
 

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