Chemical Education Today
Book & Media Reviews
edited by
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
Advanced Organic Chemistry, 4th Edition. Part B: Reactions and Synthesis by Richard J. Sundberg and Francis A. Carey Kluwer Academic/Plenum Publishers: New York, 2001. 958 pp. ISBN: 0-306-46245-1 (hardbound): $95; ISBN: 0-306-43457-1 (paper): $49.50 reviewed by Thomas G. Waddell
The first edition of this valuable advanced text appeared in 1977 and contained 521 pages. Second and third editions appeared in 1984 and 1990, respectively, with this fourth edition (2001) containing 965 pages. Why is this worth mentioning? So often organic chemistry textbooks come out in new editions every three years, and so often the length of these introductory texts increases, creating weighty tomes. As inappropriate as this is for introductory texts, the increasing length of Carey and Sundberg’s Advanced Organic Chemistry. Part B and the timely editions (every 6–10 years!) are critical necessities. For such a book, the inclusion of recent and useful organic reactions with each edition maintains the high quality and value for organic chemistry graduate students and faculty. I think that this book is one of a kind. It is a thorough reference book for reactions and synthesis; at the same time it is very readable and is presented in a pedagogical fashion. There are numerous problems at the end of each chapter for students to work, graduate students, because I think that this material is too advanced for even senior undergraduates. Here’s a typical problem of about average difficulty: “1,2,4,5Tetrazines react with alkenes to give dihydropyridazines, as illustrated below. Suggest a mechanism.” Surely this is graduate level. Nevertheless, the problems are of just the right type: writing mechanisms, predicting reaction products, outlining syntheses, explaining results. These are the kinds of questions
we ask on exams. In the text, reaction mechanisms are always illustrated clearly. An added value is that throughout this book the reactions, mechanisms, and syntheses are thoroughly referenced to the primary literature. The material of this fourth edition is very up-to-date. For example, there are good discussions of the Heck reactions, combinatorial synthesis, multistep syntheses (taxol!), modern organometallic chemistry, and the variety of modern reagents (tetrabromocyclohexadienone as a source of Br+ !). I was particularly interested in reading about modern techniques of aldol additions as found in Chapter 2. After a brief, traditional presentation of the simplest base- and acidcatalyzed reactions, there follows almost 40 pages of aldol varieties and applications, including non-traditional catalysts, stereochemical control, and achievement of enantioselectivity. Here is everything you would want to know about the timehonored aldol reaction, clearly organized and presented. There are 13 chapters. The first 12 are organized by reaction class, for example Chapter 4, Electrophilic Additions of C–C Multiple Bonds. The rationale for ordering the chapters is not apparent although it may be that the topics become more complex for the student as one proceeds. Chapter 13 is Planning and Execution of Multistep Syntheses, and includes sections on protecting groups, synthetic analysis, control of stereochemistry, examples of total syntheses, solidphase synthesis, and combinatorial synthesis; thus, the traditional, appropriate, and interesting finish. In summary, this edition will be an excellent supplement for a graduate course. Moreover, an organic chemistry graduate student should have this book on the shelf, not only as an outstanding reference for reactions and synthesis, but also to actually read, because Carey and Sundberg’s fourth edition is readable, interesting, illustrative, and necessary. Thomas G. Waddell is in the Department of Chemistry, University of Tennessee, Chattanooga, Chattanooga, TN 37403;
[email protected].
JChemEd.chem.wisc.edu • Vol. 80 No. 8 August 2003 • Journal of Chemical Education
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