Organic Stereochemistry

Number 88 in the well-known Oxford Chemistry Primer series introduces upper-undergraduate students to how the three-dimensional shapes of molecules influence their chemical and physical properties. It starts with an introduction to common stereochemical terms used throughout the book. Chapter two covers 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. 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.

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.

Introduction; Developments of methods and concepts in organic stereochemistry; Organic molecules; Shapes, Sizes and Strain problems; The changing shapes of organic molecules; Problems; Stereoisomerism in molecules and compounds; Problems; Racemates and resolution; Stereospecific and stereoselective reactions; Problems; Answers and hints

Dr Michael J T Robinson MA Dphil, Magdalen College, University of Oxford, Oxford OX1 4AU