1. Stereochemistry
Source:

2. Childish Fantasy
“Not long ago, I expressed the view that the lack of general education and of thorough training in chemistry was one of the causes of the deterioration of chemistry research in Germany …. Will anyone to whom my worries seem exaggerated please read, if he can, a recent memoir by a Herr Van’t Hoff on “The arrangement of Atoms in Space”, a document crammed to the hilt by the outpourings of a childish fantasy…..”
Written by Hermann Kolbe in 1877
Source: Solomons Organic Chemistry chapter 5

3. Significants
(R)-limonene smells of oranges while its enantiomer (S)-limonene smells of lemons
Source:

5. Constitutional Isomers
Same Molecular Formula but different Structural Formula. (Different Connectivity)

6. Diastereomers
Stereoisomers that are not mirror images of each other. Cis/Trans isomers are a type of diastereomer.

7. Diastereomers
Stereoisomers that are not mirror images of each other. Cis/Trans isomers are a type of diastereomer.

8. Enantiomers
Stereoisomers that are nonsuperposable mirror images of each other.

9. Enantiomers Enantiomers occur with chiral molecules.
Chiral from the Greek cheir meaning “Hand”.

10. Chiral Enantiomers occur with chiral molecules.
Chiral from the Greek cheir meaning “Hand”.

11. Diastereomers vs. Enantiomers
Nonsuperposable
Not Mirror Images
Differ in physical properties
Enantiomers
Mirror Images
Same physical properties

12. Existence Interaction with Enzymes and Receptor Sites
Stereospecific
Stereoselective
Rotation of Light
Dextrorotatory (Clockwise rotation)
Levorotatory (Counterclockwise rotation)
Louis Pasteur
Visual
Separated with tweezers

13. Nomenclature Systems +/- (Rotation of Light)
Right Handed / Left Handed Helix (Hand)
+/- (Rotation of Light)
D/L (Base Molecule )
R/S (Periodic Table)
Anomers (Functional Group Location)

14. Right Handed / Left Handed Helix
Right Hand Rule
Left Hand Rule

15. +/- System

16. D/L System

17. D/L System

18. D/L System

19. Anomers

20. Glycosidic Bonds

21. Glycosidic Bonds

22. Polysaccharides Glycogen Starch (amylose or amylopectin)
Storage form of glucose in Animals
Branches every 6 to 10 glucose residues
Starch (amylose or amylopectin)
Storage form of glucose in plants
Branches every 20 glucose residues
Cellulose (Fiber)
Structural component of plant cell walls
Contains β-1,4-glycosidic bonds

23. R/S System First assign priority based on Periodic Table
Second rotate lowest priority to the back

24. R/S System
Third connect three highest priorities in order

25. R/S System If clockwise assign R for Rectus
If counterclockwise assign S for Sinister

26. R/S System
Assign R and S designations to the structures

27. R/S System

28. R/S System
Assign R and S designations to each stereocenter

29. Meso

30. Meso

31. Meso

32. Structural Relationships
Same MF NO
Yes
Same Connectivity
Different NO
Yes
Superposable NO
Yes
Structural Isomers
Mirror Image & Stereocenter
Mirror Image NO
Yes
Yes NO
Diastereomers
Enantiomers
Identical
Meso

33. Problems (p. 235)
5.39
5.40
5.43
5.52