Advanced Organic Chemistry

9

Stereochemistry

LEARNING OBJECTIVES

By the end of this chapter you should be familiar with

• Representation of three dimensional molecules in two dimensions.
• The hybridization of carbon in alkanes, alkenes and alkynes.
• Chair and boat conformations, ring inversion and 1,3-diaxial interactions in cyclohexanes.
• Chirality, Fischer, Newman and saw-horse projections, R/S, erythro/threo and syn/anti configuration, meso configuration, enantiomers and diastereoisomers, racemization and resolution.

9.1 INTRODUCTION

Vladimir Prelog performed wide-ranging research on the stereochemistry of alkaloids, antibiotics, enzymes and other natural compounds. In particular, he contributed to the understanding of stereoisomerism, in which two compounds of identical ...