Understanding Stereoisomerism in C5H10 with One Cyclopropane Ring

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SUMMARY

The discussion focuses on the stereoisomerism of C5H10 compounds containing one cyclopropane ring, specifically identifying the isomers of 1,2-dimethylcyclopropane. The participants confirm that the only stereocenters present are in the cis and trans forms of 1,2-dimethylcyclopropane, which also include (S) and (R) enantiomers. It is clarified that C1 on 1,1-dimethylcyclopropane does not qualify as a stereocenter due to the lack of four distinct substituents. The isomers mentioned include cyclopentane, methylcyclobutane, and ethylcyclopropane, but only 1,2-dimethylcyclopropane exhibits stereoisomerism.

PREREQUISITES
  • Understanding of stereochemistry concepts, including stereocenters and enantiomers.
  • Familiarity with cycloalkanes, particularly cyclopropane and its derivatives.
  • Knowledge of isomerism types, specifically cis-trans isomerism.
  • Basic grasp of organic molecular structures and nomenclature.
NEXT STEPS
  • Research the stereochemistry of 1,2-dimethylcyclopropane and its cis and trans forms.
  • Study the principles of stereoisomerism in organic compounds.
  • Explore the characteristics and properties of cyclopentane and methylcyclobutane.
  • Learn about the methods for determining stereocenters in organic molecules.
USEFUL FOR

Chemistry students, organic chemists, and educators focusing on stereochemistry and isomerism in cyclic compounds.

tandoorichicken
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How many stereocenter containing isomers of c5h10 are there where the molecule must contain one ring?

I identified the cis and trans forms of 1,2-dimethylcyclopropane, but I think my TA said there was one more form containing a cyclopropane ring... but I can't remember for sure. Is C1 on 1,1-dimethylcyclopropane a stereocenter? It doesn't seem to have four different substituents.

So confusing.
 
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You're right that the C1 on 1,1-dimethylcyclopropane doesn't have four different substituents.

I can't seem to think of any other C5H10 cyclic molecules that would have a stereocenter.

The isomers of C5H10 with rings I can think of would be cyclopentane, methylcyclobutane, 1,1-dimethylcyclopropane, 1,2-dimethylcyclopropane, and ethylcyclopropane. The only ones with stereocenters are the isomers of 1,2-dimethylcyclopropane as you mentioned.
 
Hey, I got it.

There are cis and trans versions of 1,2-dimethylcyclopropane. But, within the trans isomer, there are also (S) and (R) enantiomers that are nonsuperimposable (by definition).

Hopefully I will remember all of this on the midterm
 

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