Are Alkene Diastereomers Formed Equally in Carbocation Reactions?

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In summary, the conversation discusses a lab on alkene diastereomers, specifically Maleic acid and Fumeric acid. The experiment involved dissolving Maleic acid in hot water and mixing it with hydrochloric acid to form a carbocation. The question was whether one of the diastereomers would be formed preferentially from the carbocation. The experiment showed an unknown solution to be between Maleic acid and Fumeric acid, indicating the presence of both cis and trans isomers. The concept of stability and preference in product formation is also discussed.
  • #1
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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  • #2
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.
 
  • #3
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
 

Related to Are Alkene Diastereomers Formed Equally in Carbocation Reactions?

1. What are alkene diastereomers?

Alkene diastereomers are molecules that have the same molecular formula and connectivity, but differ in the spatial arrangement of their atoms due to the presence of one or more stereogenic centers.

2. How are alkene diastereomers different from alkene enantiomers?

Alkene diastereomers have different physical and chemical properties, while alkene enantiomers have identical physical properties but may differ in their interactions with other chiral molecules.

3. What is the importance of studying alkene diastereomers?

Studying alkene diastereomers allows us to understand the relationship between molecular structure and properties, which is crucial for developing new drugs and materials with specific functions.

4. How can we distinguish between alkene diastereomers?

Alkene diastereomers can be distinguished based on their physical properties, such as melting and boiling points, as well as through analytical techniques like nuclear magnetic resonance (NMR) spectroscopy and X-ray crystallography.

5. Can alkene diastereomers interconvert?

No, alkene diastereomers cannot interconvert without breaking a covalent bond. This is due to the presence of multiple stereogenic centers, which prevent rotation around the double bond.

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