Organic Reactions And Orbital Symmetry

First published in 1979 as the second edition of a 1972 original, this textbook provides a systematic account of an important area of organic chemistry - that of cycloadditions and molecular rearrangements. The necessary theoretical background for understanding these reactions is presented in non-mathematical form and various alternative approaches to the theory are compared. The core of the book is a descriptive account of various types of cycloaddition and rearrangement reactions. The synthetic importance of these reactions is emphasised and, by providing the mechanistic background, the book demonstrates to the reader the relationship between the different types of reactions. This book will be of value to anyone with an interest in organic chemistry.

Criteria of orbital symmetry conservation had a profound influence on mechanistic thinking in organic chemistry and are still commonly applied today. The author presents a coherent set of operational rules for the analysis of scope and reliability. It is written from the viewpoint of Orbital Correspondence Analysis in Maximum Symmetry (OCAMS). Its advantage lies in its provision of a coherent overview of the relation between symmetry and mechanism. For reasons of consistency, the book remains within the framework of molecular orbital theory.

Orbital Symmetry: A Problem-Solving Approach was born of the necessity to present to students Woodward and Hoffmann's approach to pericyclic reactions. Hence the tone is introductory, and the book is addressed primarily to an audience of advanced undergraduate and beginning graduate students. The text seeks to familiarize the readers with several of the more often encountered methods of analyzing pericyclic reactions, and these methods should enable the analysis of virtually all of them. Problem solving is the foundation of the approach. Both the introductory and theory sections include problems to prepare the reader for the more extensive chapters of problems that follow. All problems (except those in Chapter VII) are answered in the text and are fully referenced where appropriate. Many of the problems require the use of molecular models if they are to be appreciated. Prentice-Hall's ""Framework Molecular Models"" and Benjamin's ""Maruzen Models"" are best suited for the construction of the highly strained molecules often encountered in the problems, and their use is recommended.

The Conservation of Orbital Symmetry examines the principle of conservation of orbital symmetry and its use. The central content of the principle was that reactions occur readily when there is congruence between orbital symmetry characteristics of reactants and products, and only with difficulty when that congruence does not obtain—or to put it more succinctly, orbital symmetry is conserved in concerted reaction. This principle is expected to endure, whatever the language in which it may be couched, or whatever greater precision may be developed in its application and extension. The book opens with a review of the elementary aspects of the molecular orbital theory of bonding. This is followed by separate chapters on correlation diagrams, the conservation of orbital symmetry, theory of electrocyclic reactions, theory of cycloadditions and cycloreversions, and theory of sigmatropic reactions. Subsequent chapters deal with group transfers and eliminations; secondary conformational effects in concerted cycloaddition reactions; and generalized selection rules for pericyclic reactions.

A practical introduction to orbital interaction theory and its applications in modern organic chemistry Orbital interaction theory is a conceptual construct that lies at the very heart of modern organic chemistry. Comprising a comprehensive set of principles for explaining chemical reactivity, orbital interaction theory originates in a rigorous theory of electronic structure that also provides the basis for the powerful computational models and techniques with which chemists seek to describe and exploit the structures and thermodynamic and kinetic stabilities of molecules. Orbital Interaction Theory of Organic Chemistry, Second Edition introduces students to the fascinating world of organic chemistry at the mechanistic level with a thoroughly self-contained, well-integrated exposition of orbital interaction theory and its applications in modern organic chemistry. Professor Rauk reviews the concepts of symmetry and orbital theory, and explains reactivity in common functional groups and reactive intermediates in terms of orbital interaction theory. Aided by numerous examples and worked problems, he guides readers through basic chemistry concepts, such as acid and base strength, nucleophilicity, electrophilicity, and thermal stability (in terms of orbital interactions), and describes various computational models for describing those interactions. Updated and expanded, this latest edition of Orbital Interaction Theory of Organic Chemistry includes a completely new chapter on organometallics, increased coverage of density functional theory, many new application examples, and worked problems. The text is complemented by an interactive computer program that displays orbitals graphically and is available through a link to a Web site. Orbital Interaction Theory of Organic Chemistry, Second Edition is an excellent text for advanced-level undergraduate and graduate students in organic chemistry. It is also a valuable working resource for professional chemists seeking guidance on interpreting the quantitative data produced by modern computational chemists.

Provides a basic introduction to frontier orbital theory with a review of its applications in organic chemistry. Assuming the reader is familiar with the concept of molecular orbital as a linear combination of atomic orbitals the book is presented in a simple style, without mathematics making it accessible to readers of all levels.