How Do I Determine (S) vs. (R) Configuration in Cyclopentanediol?

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SUMMARY

The discussion focuses on determining the stereochemistry of (1R,2R) or (1S,2S)-1,2-Cyclopentanediol based on the orientation of hydroxyl (OH) groups. The key to resolving the configuration lies in visualizing the molecule's 3D structure, specifically how the carbon atoms and their bonds are oriented in space. By rolling the molecule to view it edge-on, one can ascertain the correct stereochemical designation, confirming that the configuration is (1R,2R)-1,2-Cyclopentanediol when the OH group is positioned at the top.

PREREQUISITES
  • Understanding of stereochemistry concepts, specifically R/S nomenclature.
  • Familiarity with cycloalkane structures and their bond orientations.
  • Ability to visualize molecular structures in three dimensions.
  • Knowledge of how to represent stereochemical configurations using wedges and dashes.
NEXT STEPS
  • Study the Cahn-Ingold-Prelog priority rules for determining R/S configurations.
  • Learn how to construct and interpret molecular models for cyclic compounds.
  • Explore stereochemical representations using software tools like ChemDraw or 3D molecular visualization software.
  • Investigate other examples of stereoisomerism in cyclic compounds for broader understanding.
USEFUL FOR

Chemistry students, organic chemists, and anyone studying stereochemistry and molecular modeling will benefit from this discussion.

Chiborino
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Homework Statement


15qpwsl.jpg

A question on a pretest asks me to name this. I know it's either (1R,2R) or (1S,2S)1,2-Cyclopentanediol because the OH's are facing in opposite directions, but I'm not sure how to figure out if the OH's are S or R



2. The attempt at a solution
I somewhat have an understanding of the concept, but I'm not entirely sure how to do it with a ring structure.

To be more specific, I'm confused about how to set up the determination of S vs. R. I know I can draw the top carbon either one of these two ways:
308xfsw.jpg

I'm just not sure about how to figure out which one is actually what's being depicted
 
Last edited:
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15qpwsl.jpg

Since the carbon atoms are all depicted in the same plane, the c-c bonds also lie within the same plane. That means that of the two remaining bonds on each carbon atom, one is projecting toward the viewer (dark wedge or invisible H) and the other is projecting away from the viewer (dashed wedge or invisible H). This should be sufficient for you to construct a model.

308xfsw.jpg


Remember that in this representation, the vertical bonds are actually projecting away from the viewer, and the horizontal bonds are projecting toward the viewer.

If you're trying to visualize this rather than using an actual model, think of rolling the molecule away from you until you're looking at it edge-on, with the carbon formerly at the top now pointing away from you. The carbon at the top of the ring is now on the far side of the molecule, the C-C bonds point to the left and right (but the rotation moves them from "down" to "toward me"), the C-H bond points down and away, and the C-O bond points up and away.
 
Last edited:
PhaseShifter said:
15qpwsl.jpg

Since the carbon atoms are all depicted in the same plane, the c-c bonds also lie within the same plane. That means that of the two remaining bonds on each carbon atom, one is projecting toward the viewer (dark wedge or invisible H) and the other is projecting away from the viewer (dashed wedge or invisible H). This should be sufficient for you to construct a model.




308xfsw.jpg


Remember that in this representation, the vertical bonds are actually projecting away from the viewer, and the horizontal bonds are projecting toward the viewer.

If you're trying to visualize this rather than using an actual model, think of rolling the molecule away from you until you're looking at it edge-on, with the carbon formerly at the top now pointing away from you. The carbon at the top of the ring is now on the far side of the molecule, the C-C bonds point to the left and right (but the rotation moves them from "down" to "toward me"), the C-H bond points down and away, and the C-O bond points up and away.

So then, rolling it away from me would put the OH on top, and that would mean that it's the (1R,2R)-1,2-cyclopentanediol.

Thanks a lot. :D
 

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