Stereoisomers

The R-image increases the

bronchial airway diameter,
whereas the S-mirror image
cancels this effect and is a
suspected inflammatory agent.
What Are Isomers?
Stereoisomerisms
Mirror-Image Stereoisomerism
5-1 Mirror-Image Stereoisomerism: Chiral Molecules

H H Br H
Br2, hv
CH3 CH3
H3C H3C
H H –HBr H H
Mirror-Image Stereoisomerism: Chiral Molecules
Mirror-Image Stereoisomerism: Chiral Molecules
Mirror-Image Stereoisomerism: Chiral Molecules
Chirality in Nature
Chirality and Stereochemistry: Chiral or Achiral?
 Chirality: The Symmetry in Molecules

Chiral molecules cannot have a plane of symmetry.

 Chirality: The Symmetry in Molecules

Chiral molecules cannot have a plane of symmetry.

5-2 Optical Activity
Optical Activity: Specific Rotation
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.
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: R-S Sequence Rules
Absolute Configuration: (S)-2-Bromobutane
Absolute Configuration: (S)-2-Bromobutane
5-4 Fisher Projections
Fisher Projections
Fisher Projections: Be Careful When Rotating
Fisher Projections: Be Careful When Rotating
Fisher Projections: No Substituent Exchange!
Fisher Projections: Absolute Configuration
5-2 Molecules with Several Stereocenters: Diastereomers
Molecules with Several Stereocenters: Diastereomers
Molecules with Several Stereocenters: Diastereomers
Molecules with Several Stereocenters: Diastereomers
5-6 Meso Compounds
Meso Compounds
Meso Compounds
Meso Compounds: Cyclic Cases
5-7 Stereochemistry in Chemical Reactions
Stereochemistry in Chemical Reactions
Stereochemistry in Chemical Reactions: The Presence of C*
Stereochemistry in Chemical Reactions: The Presence of C*
Stereochemistry in Chemical Reactions: The Presence of C*
Stereochemistry in Chemical Reactions: The Presence of C*

vs
Stereochemistry in Chemical Reactions: The Presence of C*
Stereochemistry in Chemical Reactions: The Presence of C*
Stereochemistry in Chemical Reactions: Stereoselectivity
5-8 Resolution: Separation of Enantiomers
Resolution: Separation of Enantiomers
Resolution: Separation of Enantiomers
Resolution: Separation of Enantiomers
Chapter Integration Probems
Chapter Integration Probems
Chapter Integration Probems
Chapter Integration Probems
Stereoselective Reactions
Stereoselective Reactions: Formation of Enantiomers
Stereoselective Reactions: Formation of Enantiomers
Stereoselective Reactions: Formation of Enantiomers
Stereoselective Reactions: Resolution of Enantiomers
Stereoselective Reactions: Formation of Diastereomers
Stereoselective Reactions: Formation of Diastereomers
Stereoselective Reactions: Formation of Diastereomers
Stereoselective Reactions: Formation of Diastereomers
Stereoselective Reactions: Formation of Diastereomers
Stereoselective Reactions: Formation of Diastereomers
Stereoselective Reactions: Formation of Diastereomers
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Stereochemistry to Deduce Mechanism
Conformational Analysis
Conformational Analysis
A Values
Strain in Ring Systems
Stereoelectronic Effects
Stereoelectronic Effects
Stereoelectronic Effects
Stereoelectronic Effects
Stereoelectronic Effects
Stereoelectronic Effects