Chemical Education Today
Book & Media Reviews Advanced Organic Chemistry: Reactions and Mechanisms Bernard Miller. Prentice Hall: Upper Saddle River, NJ, 1998. 338 pp, index. ISBN 0-13-373275-4. $59.00.
Recently several short texts on intermediate organic chemistry have been published, intended for use in one-term courses for advanced undergraduates and for graduate students who need more background before taking a graduate-level course. These books fill a need not fully met by graduatelevel texts such as Lowry and Richardson’s Mechanism and Theory in Organic Chemistry or Carey and Sundberg’s Advanced Organic Chemistry. The pedagogic philosophy behind Advanced Organic Chemistry: Reactions and Mechanisms is pithily explained in Miller’s introduction: in order to maintain student interest, advanced topics are introduced early and theory is presented in context. Miller meets these goals admirably. The discussions are pellucid, and I found myself enjoying the book immensely. Miller presents material in a nonstandard order, choosing to handle chemistry often neglected in basic organic courses first, and introducing bonding theory and concepts as they are needed to explain the reactions being discussed. He wisely includes a two-chapter module on heterocyclic chemistry, pointing out that this topic is essential to biochemistry but typically neglected by introductory organic chemistry texts. Each chapter is extensively referenced to the primary and secondary literature. Advanced Organic Chemistry offers exciting, indeed almost breakneck, coverage of the most interesting topics in physical organic chemistry. The first chapter presents a thorough discussion of what many students somehow don’t pick up during organic chemistry: how to push electrons. This leads to a discussion of Lewis structures and resonance theory. However, students are not allowed to bask very long in this simple model, because they are immediately plunged into three chapters of electrocyclic and sigmatropic reactions, in which Miller introduces molecular orbital theory, orbital symmetry, and frontier orbital interactions. He then turns to the application of these principles to charged species: cationic rearrangements and nonclassical cations occupy two chapters, and two more chapters cover rearrangements and reactions of carbanions, free radicals, and 6-electron neutral species. The presentation of all this in only 11 chapters (including the two on heterocycles) means that, while the pace is rapid, it is not too rapid for a one-semester course for undergraduates.
Nevertheless, this book is not perfect. There are not as many practice problems as would be desirable. The problems are good, but neither answers nor leading references are provided for most of them. Lack of problems, and of answers and references, is a serious deficiency for a topic in which practice is the sine qua non, and I found myself missing Lowry and Richardson’s extensive, fully referenced problem sets. There is no presentation of chemical kinetics. While kinetics is used to discuss certain reactions, there is no specific discussion of this essential topic. Instead Miller appears to assume that his students fully remember whatever exposure they had to rate laws in general chemistry. I was impressed by the concise yet thorough discussion of polar, resonance, and steric free-energy relationships that occupies Chapter 5; but this material does not seem to be connected to anything else in the text, and one feels that Miller is presenting the information because it’s expected of him. Miller has kept his text short and interesting by dealing exclusively with topics that most physical organic chemists— including this writer—find sexy: rearrangements and pericyclic processes, with a liberal dose of nonclassical species and electron-deficient neutral species. He is to be especially applauded for his insistence on including two chapters of heterocyclic chemistry. On the other hand, the short shrift given to kinetics and to bread-and-butter physical organic chemistry (e.g., nucleophilic and electrophilic substitution reactions) means that students do not have a chance to deepen their knowledge of these topics during the course. This objection carries less weight for students en route to graduate school, where they will be confronted with a more conventional and thorough physical organic chemistry course. But it is, I think, a problem for the student who is planning to teach high school or to go directly into industry, where more “boring” organic reactions are of great importance. The other problem I have with this text is the price. Maybe I'm old fashioned, but I still consider the price of the text as one of the factors in a decision to adopt. A short text should be inexpensive enough to give the instructor freedom in assigning students to buy supplementary material, but at $59.00 I found Miller’s book a little rich for my blood. I would love to use Miller’s book for my advanced organic chemistry course. It is lucid, interesting, and well paced and concentrates on subjects too often neglected. But the failure to treat kinetics—together with the price, which makes it harder to include supplemental material on kinetics while keeping the course price reasonable—does not allow me to do so. Nevertheless, I recommend this book for departments that have a separate kinetics course. Daniel J. Berger Bluffton College Bluffton, OH 45817-1196
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Journal of Chemical Education • Vol. 75 No. 12 December 1998 • JChemEd.chem.wisc.edu
