A thorough understanding of stereochemistry is essential for the comprehension of almost all aspects of modern organic chemistry. It is also of great significance in many biochemical and medicinal disciplines, since the stereoisomers of a compound can have dramatically different biological properties. This text explains how the different properties of stereoisomers of a compound arise, and what processes can be used to prepare and analyze stereoisomerically pure compounds. It also presents prominent coverage of the stereochemistry of inorganic and organometallic compounds, which is likely to increase in importance, as these compounds are used as symmetric catalysts in asymmetric synthesis. Modern stereochemical terminology is used throughout, although reference is also made to older terms which are still widely used. A set of problems at the end of each chapter aims to further the reader's understanding of how the content can be applied. The book is designed mainly as a textbook for undergraduate students and as a reference source for more advanced levels, but is also intended for academic and professional organic chemists.
Isomerism
Drawing Three Dimensional Chemical Stuctures
VSEPR and the Shape of Molecules
Structure and Bonding
Clasification of Stereoisomers
CIS-TRANS ISOMERISM
Cis-Trans Isomerism in Alkenes
Cis-Trans Isomerism in Other Systems Which Contain a double Bond
Cis-Trans Isomerism in Cyclic Systems
Cis-Trans Isomerism in Square Planar and Octohedral Metal Complexes
Cis-Trans Isomerism about Single Bonds (Conformational Diastereomers)
Methods for Distinguishing Cis-Trans Isomers
ENANTIOMERS
Structure of Enantiomers
Nomenclature for Enantiomers (Speciation of Absolute Configuration)
Chemical Properties of Enantiomers
Physical Properties of Enantiomers
Enantiomeric Excess
Biological Properties of Enantiomers
Chirality Due to Stereocentres at Atoms Other than Carbon
Other Stereogenic Elements Which Can Produce Molecular Chirality
COMPOUNDS WITH TWO OR MORE STEREOCENTRES
Compounds with Two Stereocentres
Compounds with More Than Two Stereocentres
Polymer Stereochemistry
Relative Stereochemistry Nomenclature
Diastereomeric Excess
INTERCONVERSION AND ANALYSIS OF STEREOISOMERS
Racemization
Epimerization
Resolution
Methods for Determining Enantiomeric Excess
Determination of Absolute Configuration
Determination of Relative Configuration
MOLECULAR SYMMETRY
Introduction
Symmetry Elements and Symmetry Operations
Symmetry of Molecules with Multiple Conformations
Point Groups
Symmetry and Chirality
TOPISM AND PROSTEREOGENICITY
Homotopic, Enantiopic and Diastereotopic Groups
Homotopic, Enantiopic and Diastereotopic Faces
Nomenclature for Heterotopic Groups and Faces
CONFORMATION OF ACYLIC AND CYCLIC MOLECULES
Introduction
Conformations of Acyclic Molecules
Conformations of Cyclic Alkanes and their Derivatives
Cyclopropane
Cyclobutane
Cyclohexane
Medium and Large Rings
Conformation of Inorganic and Organometallic Compounds
Conformation of Biopolymers
Methods for Determining Molecular Conformation
STEREOCHEMISTRY OF CHEMICAL REACTIONS
Introduction
Substitution Reactions
Elimination Reactions
Addition Reactions to Alkenes
Addition of Nucleophiles to Aldehydes and Ketones
Pericyclic Reactions
ASYMMETRIC SYNTHESIS
Introduction
Use of Chiral Auxiliaries
Use of Enantiomerically Pure Reagents
Index
Biography
North, Michael
