Organic Stereochemistry

This book is an account for students of how the three-dimensional shapes of molecules influence their chemical and physical properties. It begins with the structures of molecules and then describes how such structures can be changed.

A short historical introduction serves to introduce many common stereochemical terms used throughout the book. Chapter two is an account of the structures of simple unstrained organic molecules followed by examples of strained molecules. The third chapter deals with conformational analysis of acyclic and carbocyclic molecules, ending with a short exposition of molecular mechanics. Chapter four is about stereoisomerism in molecules and compounds. A full description of enantiomerism and diastereomerism is followed by an explanation of the nomenclature for absolute and relative configurations of molecules and for topism. A short chapter describes racemates, their resolution, and methods for determining enantiomeric purity. The book concludes with a survey of stereoselective and stereospecific reactions, including the use of chiral catalysts and auxiliaries, rules for predicting stereoselectivity, and double asymmetric synthesis.