Chemical Education Today
Book & Media Reviews Advanced Organic Chemistry, Part A: Structure and Mechanism, 4th Edition by Francis A. Carey and Richard J. Sundberg Plenum: New York, 2000. 823 pp. Hardcover: ISBN 0-30646242-7. $94.50. Paperback: ISBN 0-306-46243-5. $49.50. reviewed by R. Daniel Libby
It has been 10 years since the last edition of this standard text/reference for upper-level undergraduate and graduate students in physical organic chemistry. In the preface to this edition, the authors state, “The goal of this text is to build on the foundation of introductory organic chemistry to provide students and other readers a deeper understanding of structure and mechanism and the relationships between them.” As in the previous editions, they have reached their goal. Their discussions begin at a level accessible to most upper-level undergraduate and first-year graduate students and develop the topics to a level that would be expected of a Ph.D. in organic chemistry. They also appear to have reasonably covered the literature through 1998–1999. However, they largely used the text, examples, and problems of the third edition in their efforts. The major changes are related to the application of computational methods to many of the specific reactions discussed. Although the additions are appropriate, they represent less than 10% of the new edition. The chapter organization is the same as in the third edition. The first three chapters deal with data and theories that help us understand organic structure and develop the fundamentals of bonding, stereochemistry, and conformational analysis to provide a firm structural basis for understanding the reactions considered in later chapters. Both valence-bond and molecular-orbital approaches are presented and their specific strengths compared. A new section in Chapter 1 presents recent developments in molecular orbital theory including density functional theory, and there are 3 new problems. Chapter 2 introduces some new methods for resolving racemic mixtures and a few new chiral catalysts, but no new problems. Although there are 5 new problems and a few new references in Chapter 3, its treatment of conformational analysis is es-
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sentially the same as in the previous edition. Chapter 4 discusses physical methods for studying reaction mechanisms. Included are thermodynamics and kinetics, isotope effects, characterization of intermediates, acid–base catalysis, and solvent effects. Gone is third-edition material on the Swain–Lupton approach to linear free energy relationships and added is new material on Lewis acid catalysis along with 3 new problems. Chapters 5 through 11 deal with mechanisms of the major ionic organic reactions: nucleophilic substitution, polar addition and elimination, carbanion, carbonyl, aromatic substitution, and pericyclic reactions. In each case evidence for and examples of the predominant mechanisms are thoroughly presented. There is considerable new material on carbocation rearrangements and nonclassical cations (Chapter 5), new data on substituent effects on carbonyl group stability (Chapter 8), and calculations of activation hardness of aromatic and heteroaromatic compounds (Chapter 10), together with 15 new problems in these 7 chapters. Free radical reactions are considered in Chapter 12. The discussion begins with consideration of the structure and stabilities of free radicals and then follows through with treatment of the mechanisms of the major types of free radical reactions. A new section on free radical halogen, sulfur, and selenium group transfer reactions, several new references, and 1 new problem are included. Chapter 13 deals with photochemistry. Orbital symmetry considerations are developed and applied to reactions of alkenes and dienes as well as carbonyl and aromatic compounds. There are several new references and 2 new problems. In all of the reaction chapters, the treatment of the material is quite complete and there are new references in all chapters, but the discussions of the reactions and the examples used have changed little from the third edition. So the fourth edition of Carey and Sundberg continues the text’s 20+ year tradition as an excellent reference for physical organic chemists. It should be strongly considered as a text for any advanced undergraduate or graduate physical organic course. However, those who have the third edition and use it as an occasional general reference might wish to evaluate the new edition before considering a purchase. R. Daniel Libby is in the Chemistry Department, Moravian College, Bethlehem, PA 18018;
[email protected].
Journal of Chemical Education • Vol. 78 No. 3 March 2001 • JChemEd.chem.wisc.edu
