Stereoisomers What Are Isomers?

The R-image increases the

bronchial airway diameter,
whereas the S-mirror image
cancels this effect and is a
suspected inflammatory agent.
1 2

Stereoisomerisms Mirror-Image Stereoisomerism

3 4
5-1 Mirror-Image Stereoisomerism: Chiral Molecules Mirror-Image Stereoisomerism: Chiral Molecules

H H Br H
CH3 Br2, hv CH3
H3C H3C
H H –HBr H H

5 6

Mirror-Image Stereoisomerism: Chiral Molecules Mirror-Image Stereoisomerism: Chiral Molecules

7 8
 Chirality in Nature Chirality and Stereochemistry: Chiral or Achiral?

9 10

Chirality: The Symmetry in Molecules Chirality: The Symmetry in Molecules

Chiral molecules cannot have a plane of symmetry. 11 Chiral molecules cannot have a plane of symmetry. 12
 5-2 Optical Activity Optical Activity: Specific Rotation

13 14

Optical Activity: Specific Rotation 5-3 Absolute Configuration

There is no straightforward correlation between the sign of rotation

and the structure of the particular enantiomer.

15 16
Absolute Configuration: R-S Sequence Rules Absolute Configuration: R-S Sequence Rules

17 18

Absolute Configuration: R-S Sequence Rules Absolute Configuration: R-S Sequence Rules

19 20
Absolute Configuration: R-S Sequence Rules Absolute Configuration: R-S Sequence Rules

21 22

Absolute Configuration: R-S Sequence Rules Absolute Configuration: R-S Sequence Rules

23 24
Absolute Configuration: R-S Sequence Rules Absolute Configuration: (S)-2-Bromobutane

25 26

Absolute Configuration: (S)-2-Bromobutane 5-4 Fisher Projections

27 28
 Fisher Projections Fisher Projections: Be Careful When Rotating

29 30

Fisher Projections: Be Careful When Rotating Fisher Projections: No Substituent Exchange!

31 32
 Fisher Projections: Absolute Configuration 5-2 Molecules with Several Stereocenters: Diastereomers

33 34

Molecules with Several Stereocenters: Diastereomers Molecules with Several Stereocenters: Diastereomers

35 36
Molecules with Several Stereocenters: Diastereomers Molecules with Several Stereocenters: Diastereomers

37 38

5-6 Meso Compounds Meso Compounds

39 40
 Meso Compounds Meso Compounds: Cyclic Cases

41 42

5-7 Stereochemistry in Chemical Reactions Stereochemistry in Chemical Reactions

43 44
Stereochemistry in Chemical Reactions: The Presence of C* Stereochemistry in Chemical Reactions: The Presence of C*

45 46

Stereochemistry in Chemical Reactions: The Presence of C* Stereochemistry in Chemical Reactions: The Presence of C*

vs

47 48
Stereochemistry in Chemical Reactions: The Presence of C* Stereochemistry in Chemical Reactions: The Presence of C*

49 50

Stereochemistry in Chemical Reactions: Stereoselectivity 5-8 Resolution: Separation of Enantiomers

51 52
Resolution: Separation of Enantiomers Resolution: Separation of Enantiomers

53 54

Resolution: Separation of Enantiomers Chapter Integration Probems

55 56
 Chapter Integration Probems Stereoselective Reactions

57 58

Stereoselective Reactions: Formation of Enantiomers Stereoselective Reactions: Formation of Enantiomers

59 60
Stereoselective Reactions: Formation of Diastereomers Stereoselective Reactions: Formation of Diastereomers

61 62

Stereoselective Reactions: Formation of Diastereomers Stereoselective Reactions: Formation of Diastereomers

63 64
Stereoselective Reactions: Formation of Diastereomers Stereoselective Reactions: Formation of Diastereomers

65 66

Stereoselective Reactions: Formation of Diastereomers Stereochemistry to Deduce Mechanism

67 68
Stereochemistry to Deduce Mechanism Stereochemistry to Deduce Mechanism

69 70

Stereochemistry to Deduce Mechanism Stereochemistry to Deduce Mechanism

71 72
Stereochemistry to Deduce Mechanism Stereochemistry to Deduce Mechanism

73 74

Stereochemistry to Deduce Mechanism Conformational Analysis

75 76
Conformational Analysis A Values

77 78

Strain in Ring Systems Stereoelectronic Effects

79 80
Stereoelectronic Effects Stereoelectronic Effects

81 82

Stereoelectronic Effects Stereoelectronic Effects

83 84
Stereoelectronic Effects

85