Menthol Steioisomers

The JCE Featured Molecules for July come from the paper An Engaging Illustration of the Physical Differences among Menthol Stereoisomers by Edward M. Treadwell and T. Howard Black on the use of commercially available stereoisomers of menthol to illustrate properties of enantiomers and diastereomers. The paper describes the use of four of the eight possible stereoisomers. Structures of all eight stereoisomers are included in this month's molecule collection, labeled by the chirality of the three chiral atoms. In addition to the exercises described in the paper, students can be asked to match the appropriate structures to those shown in the paper, or to generate structures for the isomers that are not discussed.
Menthol Steioisomers   
(Interactive Simulation (1))