Chap 5: Stereochemistry

Outline
• Chirality
• Cahn - Ingold – Prelog RULES
(R and S configurations)
• Compounds with one chiral center
(enantiomers): : Optical activity
• Compounds with two chiral centers
(diastereomers)
• Meso compounds and achiral compounds
OWL: Draw the other enantiomer of compound (1):

(1)
OWL: Draw the other enantiomer of compound (1):

(1)
Compounds with Two Asymmetric Centers
Compounds with Two Asymmetric Centers

maximum # of stereoisomers = 2n
(n = # of asymmetric centers)
 How to differentiate between
Enantiomers and Diastereomers?

• Enantiomers are stereoisomers that

are mirror image to each other.

▪ Diastereomers are stereoisomers

that are not mirror image to each
other.
Compounds with Two Asymmetric Centers
maximum # of stereoisomers = 2n
(n = # of asymmetric centers)

1 and 2 are enantiomers. 3 and 4 are enantiomers.

 Meso Compounds
Definition: Meso compounds are stereoisomers
but have internal plane of symmetry.
All Meso compounds are achiral (not chiral)
compounds.

tartaric acid
Meso Compounds:
• Tartaric acid has two chirality centers and two diastereomeric forms tartaric acid
Meso Compounds
• An achiral compound with chirality centers is called a meso
compound – it may have a plane of symmetry
• The two structures 2R, 3S and 2S,3R are identical so the compound
(2R, 3S) is achiral

End of Chap 5
•Student’s Questions

• OWL questions
 What is the relationship between each pair of
molecules shown below?

A. enantiomers
B. Diastereomers
C. Identical
D. Constitutional isomers
OWL questions: Classify the following compounds
as chiral, achiral (but not meso), or meso.
OWL questions: Classify the following compounds
as chiral, achiral (but not meso), or meso.