CHAPTER NINE

Stereochemistry

Learning Objectives: You should be able to interconvert Fischer projections, tetrahedral configurations, and perspective drawings and to determine R and S configuration on all three types of representations. It is also important to recognize enantiomers, diastereomers, and meso compounds of chains and ring systems.

Chiral molecules

9.1, 9.2

Stereogenic centers

9.3, 9.13, 9.35

Assign priority using Cahn-Ingold Prelog rules

Assign R and S configurations

9.7, 9.9, 9.10, 9.41, 9.42

Identify and draw stereoisomers

9.4, 9.8, 9.13, 9.23, 9.24, 9.29, 9.30, 9.31, 9.32, 9.33, 9.38, 9.39

Identify meso isomers and symmetry planes

Fischer projections

9.15, 9.16, 9.17, 9.45, 9.46, 9.47, 9.48, 9.49, 9.50

Draw chiral molecules

9.8, 9.31, 9.33, 9.34, 9.43, 9.44, 9.59

Apply stereochemistry to the outcome of a reaction

9.18, 9.19, 9.20, 9.21, 9.22, 9.52, 9.55

Terminology

9.28