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Chapter 7: Stereochemistry



Summary | Isomer types | Enantiomers | The Stereogenic center | Optical Activity | Absolute Relative Configuration | Cahn-Ingold-Prelog R/S notation | Fischer projections | Self Assessment | Quiz |


Cahn-Ingold-Prelog R/S Notation

Chapter 7 : Stereochemistry

The Cahn-Ingold-Prelog R/S rules are used for naming enantiomers.

NB: The term stereogenic has superceded the term chiral.

1. Identify the stereogenic centers (most commonly an sp3 C with 4 different groups attached)
2. Assign the priority to each group (high = 1, low = 4) based on atomic number of the atom attached to the stereogenic center
3. Position the lowest priority group away as if you were looking along the C-(4) sigma bond. If you are using a model, grasp the group in your fist
4. For the other 3 groups, determine the direction of high to low priority (1 to 3)
5. If this is clockwise, then the center is R (Latin: rectus = right)
6. If this is counter clockwise, then it is S (Latin: sinister = left)

Example: chlorofluoroiodomethane

The stereogenic center is easy to spot, and the four attached groups are I (purple), Cl (green), F(brown) and H (white), listed in priority order, highest to to lowest. Rotate the CHIME image below so the you are looking along the C-H bond and the H is away from you, then determine the direction of high to low priority. It decreases clockwise, so this is the R enantiomer.

Subrules:

 Can you convey this on a piece of paper?


 


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