Chemical Education Today
Book & Media Reviews Organic Chemistry. A Brief Survey of Concepts and Applications, 6th Edition by Philip S. Bailey Jr. and Christina A. Bailey Prentice Hall: New York, 2000. xi + 542 pp. Figs. and tables. Softcover, 20.5 × 25.5 cm. ISBN 0-13-924119-1. $70.67. reviewed by Alan M. Rosan
The introductory survey text Organic Chemistry, by Bailey and Bailey, has admirably served the needs of the short, one-semester or one- to two-quarter organic course for the past 22 years. This sixth edition, appearing five years after the fifth, is an updated stalwart successor to this line. It comprises 18 chapters, a seven-page four-part appendix on nomenclature, a seven-page 315-item glossary, and full 12-page index. At a feathery 2.3 pounds, this softback edition is dense, compact, and easily brought to class. The text, constructed in short, digestible sections that facilitate information retrieval and retention, emphasizes learning as an activity and is coherent both in content and presentation; 10 of the 18 chapters are 31–36 pages in length and 6 are 20–27 pages long. Worked in-chapter and end-ofchapter problems (from 7 to 34 per chapter, 800 in all) of varying degrees of difficulty are offered. The in-chapter problems are specifically linked to related end-of-chapter problems, which are arrayed in clearly delineated categories designed to help students focus on selected areas. In-chapter critical thinking exercises called “getting involved”, found on nearly every page, liberally enhance the text and encourage students to continually test and apply their learning. In addition, most of the chapters include a very useful set of from 2 to 7 molecular model building activities. However, the four chapters on carbohydrates, lipids, proteins, and nucleic acids coming near the end of the text strangely do not include any recommended exercises on assembling model structures of biomolecules. Finally, each chapter is accompanied by one or more “connection boxes”, which highlight, on a calming lilac blue page, a significant and timely connection to organic chemistry. Included among the 46 connections offered are illuminating and cogent discussions of such varied and important topics as mad cow disease, plastics recycling, insecticides and nerve gases, diabetes, drug design, DNA fingerprinting, and the human genome project. These are the jewels of this text and I found much fascinating, timely, and insightful information here. The thrust of this text is twofold: an elaboration of organic structure and organic reactions with an emphasis on what types of reactions are observed rather than on their mechanisms, and an exposé of the import of organic chemistry in the broader world with particular focus on biological applications. It admirably lives up to its subtitle, a brief survey
of concepts and applications, and is replete with original and useful analogies that will help students understand resonance, aromaticity, polarization, and geometric isomers. For example, the last are likened to the structural rigidity accompanying the nailing of two boards together with either one or two nails. The discussion of acidity is particularly lucid. I also found the description of the assignment of R and S stereoisomers refreshingly clear. The writing style is friendly, fresh, and crisp and numerous renditions of various structural models are sprinkled throughout, although occasionally some of the line drawings (batrachotoxin, page 454) lack suitable wedges and dashes and tend to be flat. Reactive functionality appears in blue. Those who seek the full palette of organic transformations will find this text abbreviated. Mechanistic details for all but the most fundamental processes are often condensed, (peracid epoxidation, oxymercuration, ozonolysis), and certain specific processes and ideas are absent altogether (hydroboration, cycloaddition, partial hydrogenation, dissolving metal reduction, MO theory, enantiotopic atoms, etc.). However, the authors have carefully crafted a book that speaks to the needs of those who teach and those who learn in a singleunit basic organic chemistry course. In doing so they have wisely chosen to focus on the fundamentals and to emphasize the myriad essential links between organic structure, function, and reactivity and the biological, economic, environmental, and social world. The book is substantially free of errors and I found only a handful of grammatical oversights (pages 152, 165, 479). Most problematic are a confusion between α and [α] (page 198), a definition of mass spectrometry involving fragmentation by radiation (glossary G4), a typo in a modelbuilding exercise on the construction of 2,3-dibromobutane (page 218), and the implication that multiphoton processes do not occur (page 516). A carbon NMR spectrum (page 534) is drawn so as to suggest that J is not constant and, while described in words, the phrase “n + 1” is surprisingly absent. Lastly, I do not agree that the sawhorse diagram (page 54) is entirely self-evident to students. But, in proper perspective, these are all minor points. This latest edition, as those before it, ably and enthusiastically illustrates the wide range, deep uniformity, and undeniable centrality of organic chemistry in a molecular understanding of the architecture and applicability of topics ranging from buckyballs to biochemistry. Considerable thought has gone into illuminating the essentials of organic structural change and in presenting these concepts and connections clearly and simply. This text has much to recommend it as an excellent choice for the short or even the not-so-short course. Alan M. Rosan is in the Department of Chemistry, Drew University, Madison, NJ 07940;
[email protected].
JChemEd.chem.wisc.edu • Vol. 78 No. 7 July 2001 • Journal of Chemical Education
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