Chiral Center Priority: Determining R and S Configurations Using CIP Rules

  • Thread starter Thread starter Destroxia
  • Start date Start date
  • Tags Tags
    Chiral
Click For Summary

Discussion Overview

The discussion revolves around determining the R and S configurations of a chiral center using Cahn-Ingold-Prelog (CIP) priority rules. Participants explore the assignment of priorities to substituents attached to a chiral carbon atom.

Discussion Character

  • Homework-related
  • Technical explanation

Main Points Raised

  • One participant presents a specific chiral center with substituents H, CH3, OH, and CH2CH2OH, and proposes a priority assignment based on CIP rules.
  • The participant suggests that OH should take priority over CH2CH2OH because it is directly attached to the chiral carbon, raising a question about how to handle substituents with similar functional groups.
  • Another participant points out that the determination of chirality may depend on the choice of convention, implying that different interpretations could exist.
  • A later reply reiterates the importance of using the CIP rules for determining R and S configurations without providing further clarification.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the priority assignment, and there are competing views regarding the interpretation of substituent priorities and the implications of convention in chirality determination.

Contextual Notes

There is uncertainty regarding the treatment of substituents with similar functional groups, and the discussion does not resolve how to apply the CIP rules in this specific case.

Destroxia
Messages
204
Reaction score
7

Homework Statement



Say you have a chiral center carbon, attached to it are a H, a CH3, an OH, and a CH2CH2OH. The H is pointing away from you, and in a clockwise direction it goes, CH3, OH, CH2CH2OH

My question is what is the priority of this? My main confusion is in the fact that since both the OH and CH2CH2OH have an OH in them, does the OH take priority since it is directly connected to the carbon? As in, do you just stop right there, and you know it has more priority?

The Attempt at a Solution



This is what I THINK it should be...

Priorities:
H: (4)
CH3: (3)
OH: (1)
CH2CH2OH: (2)

Therefore, it goes from OH, to CH2CH2OH, to CH3, which is a clockwise direction, therefore it is R ?
 
Physics news on Phys.org
RyanTAsher said:
R and S.
Then, one uses "C-I-P" detailed in the link.
 

Similar threads

  • · Replies 1 ·
Replies
1
Views
1K
  • · Replies 4 ·
Replies
4
Views
9K
  • · Replies 4 ·
Replies
4
Views
2K
  • · Replies 6 ·
Replies
6
Views
2K
  • · Replies 2 ·
Replies
2
Views
5K
  • · Replies 2 ·
Replies
2
Views
2K
  • · Replies 2 ·
Replies
2
Views
3K
Replies
2
Views
2K
Replies
2
Views
5K
  • · Replies 1 ·
Replies
1
Views
2K