Chapter 9 Stereoisomers: Chirality, Enantiomers, and Diastereomers

This chapter focuses on a class of isomers that differ only in the spatial arrangement of attached atoms and groups about an atom. Enantiomers are different molecules, and each requires a unique name. A set of standardized rules of nomenclature have been developed that distinguish two enantiomers based on the relative position of atoms or groups. A chiral compound that is not enantiopure is a mixture of both enantiomers. Electromagnetic radiation travels as a transverse wave that consists of electric and magnetic fields that oscillate perpendicular to one another. A transverse wave oscillates perpendicular to the direction of the wave's advance. Stereogenic carbons are found in cyclic molecules but monosubstituted cycloalkanes are not chiral.

Defining a Stereogenic Center

Enantiomers and Non-Superimposability

Fischer Projections

Cahn-lngold-Prelog Selection Rules

Chiral Molecules with Substitution

Specific Rotation

Diastereomers and the 2" Rule

Meso Compounds

Stereoisomers in Cyclic Molecules

cis-transand E-Z Nomenclature

Bicyclic Compounds

Optical Resolution

Circular Dichroism