R/S Configuration of Compounds

In summary, the conversation revolved around a question in the International Chemistry Olympiad Paper about determining the R configuration. Two structures were drawn incorrectly, causing confusion for the participants. After struggling with the question, the conclusion was reached that the first structure was R. However, the official answer key released by the institute stated the second structure as the correct answer.
  • #1
AGNuke
Gold Member
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I got this problem today in my International Chemistry Olympiad Paper, quite bugging me this question, so I am better off asking it.

My question is, which of the following has R configuration?

ICho.png



From what I tried, I got both of them as S, and the remaining two options being confirmed S. I got it wrong, but it wouldn't hurt (or it would) to know the right answer.
 
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  • #2
Were they drawn like this? Usually the two groups in the plane of the paper are adjacent rather than opposite as BOTH of these structures are! Redraw them correctly and the answer will present itself.
 
  • #3
Yes, they were drawn like this. That's why it posed a problem to me.
 
  • #4
So, redraw them and the answer will be obvious.
 
  • #5
Alright, after a lot of struggle, I reached the conclusion that 1st one is R.
 
  • #6
Me too.
 
  • #7
UPDATE : In the answer key released by my institute, the answer mentioned is the second one... :confused:
 

1. What is the R/S configuration of a compound?

The R/S configuration is a method used to describe the spatial arrangement of atoms in a molecule. It is determined by the relative positions of the substituent groups attached to the chiral center of a molecule.

2. How is the R/S configuration determined?

The R/S configuration is determined by the Cahn-Ingold-Prelog (CIP) priority rules. These rules assign a priority to each substituent group based on the atomic number of the atoms directly bonded to the chiral center. The group with the highest atomic number is given the highest priority, and the lowest priority group is oriented away from the viewer.

3. What is the difference between R and S configuration?

The R configuration refers to the clockwise arrangement of the substituent groups around the chiral center, while the S configuration refers to the counterclockwise arrangement. This is based on the CIP priority rules, where the substituent groups are arranged in order of decreasing priority.

4. Can a compound have both R and S configurations?

No, a compound cannot have both R and S configurations. This is because the R and S configurations are enantiomers of each other, meaning they are mirror images that cannot be superimposed on each other. A molecule can only have one unique R or S configuration.

5. How does the R/S configuration affect the properties of a compound?

The R/S configuration can have a significant impact on the properties of a compound, particularly its biological activity. This is because enantiomers have different interactions with other molecules, such as enzymes and receptors, due to their different spatial arrangements. As a result, one enantiomer may have a desired effect while the other may have no effect or even be harmful.

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