Chapter 5 - Multiple Stereocenters

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6 Terms

1
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Meso compound

LOOKS like an enatiomer, but ACTUALLY is identical molecule

  • if there is a line of symmetry, the molecule is achiral and meso


2
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enatiomer

ALL stereocenters are inverted
- mirror images, not superimposable

3
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diastereomer

NOT ALL stereocenters inverted

-stereoisomers, not mirror images

4
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Max # of stereoisomers

2^n, where n= # of stereocenters

5
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How to find R vs S configuration

R → clockwise

S → counterclockwise

  • But, switch S to R or R to S ONLY IF priority #4 is NOT a dashed line


process (refresher):

  1. assign priorities to each group attached to the chiral carbon (1 is the highest atomic number)

  2. move clockwise/counterclockwise (if the numbers are not in order just skip over #4)

  • note: if you have a group like OH for example with 2 atoms, just count the oxygen bc hydrogen is not important


6
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How to find chiral carbons

  • carbons with double or triple bonds CANNOT be chiral

  • CH3 and CH2 carbons CANNOT be chiral

  • chiral carbons are attached to 4 different groups