Meso Compounds with an odd number of chiral centers

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Discussion Overview

The discussion revolves around the concept of meso compounds in organic chemistry, specifically addressing the possibility of meso compounds having an odd number of chiral centers. Participants explore definitions and implications of chirality and stereochemistry.

Discussion Character

  • Conceptual clarification
  • Debate/contested

Main Points Raised

  • One participant questions whether a meso compound can exist with an odd number of chiral centers, noting that they can conceptualize meso compounds with an even number of chiral centers.
  • Another participant suggests a specific example, (1R, 2S, 4R)-1,2,4-cyclopentanetriol, as a potential meso compound with an odd number of chiral centers.
  • A third participant emphasizes the importance of distinguishing between "chiral center" and "stereocenter," arguing that while a meso compound cannot have 2n+1 chiral centers, the definitions of these terms are not interchangeable.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the original question of whether meso compounds can have an odd number of chiral centers, and there is ongoing debate regarding the definitions and implications of chirality and stereochemistry.

Contextual Notes

There are nuances in the definitions of "chiral center" and "stereocenter" that may affect the understanding of the discussion. The implications of these definitions on the existence of meso compounds with odd numbers of chiral centers remain unresolved.

thefan
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I was learning about chirality in my organic chemistry class when we were talking about meso compounds. The professor stated that for a compound to be meso, you needed there to be two or more chiral centers. After thinking about it for a while, I can come up with abstract structures for meso compounds with 2, 4, ..., 2n chiral centers, but can't come up with one that has 2n+1 chiral centers. Is it possible to have a compound with an odd number of chiral centers that is meso?
 
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thefan said:
I was learning about chirality in my organic chemistry class when we were talking about meso compounds. The professor stated that for a compound to be meso, you needed there to be two or more chiral centers. After thinking about it for a while, I can come up with abstract structures for meso compounds with 2, 4, ..., 2n chiral centers, but can't come up with one that has 2n+1 chiral centers. Is it possible to have a compound with an odd number of chiral centers that is meso?

Sure, try (1R, 2S,4r)-1,2,4-cyclopentanetriol or similar.
 
you have to be careful with how you through around the terms "stereocenter" and "chiral center." If your instructor said "A meso compound cannot have 2n+1 number of CHIRAL centers," then they are correct. It would be incorrect to say "a meso compound that contains STEREOcenters must have 2n stereocenters." In other words, these terms do not have the same meaning. All chiral centers are stereocenters, and not all stereocenters are chiral centers. the term "stereocenter" or "stereogenic center" means that swapping two groups on that center would give a different stereoisomer, whereas "chiral center" means that the atom doesn't occupy a molecular plane of symmetry (4 different substituents bonded to the atom).
 

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