Chemical Education Today edited by
Book & Media Reviews
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
Organic Chemistry: An Intermediate Text, Second Edition by Robert V. Hoffman Wiley-Interscience, Hoboken, NJ, 2004. 476 pp. ISBN 0471450243 (cloth), $99.95 reviewed by Thomas G. Waddell
Chemistry textbooks are so much better now than in the old days, meaning the 1950s and the 1960s. Back then, each page of a text was intimidating in detail, cold in style, and stark in its lack of illuminating illustrations. I am not imagining this. Learning physical chemistry from the second edition of Daniels and Alberty (1) was a chilling experience. Happily, we have Organic Chemistry: An Intermediate Text, 2nd Edition. This book will be excellent for a senior-undergraduate course in advanced organic or a required course for first-year organic graduate students. The book’s most striking qualities are these. It is appropriately concise yet written in a clear and very student-friendly style. The organization of the topics is logical and pedagogically sound: functional groups → bonding → oxidation states → acids–bases → mechanism and stereochemistry → synthesis. The last chapter (13) on structure determination does a wonderful job of taking the reader from the basics of the “big 3” (NMR, IR, MS) to a practical level of application and use. I have shown Chapter 13 to an organic colleague who was especially interested in the spectroscopy discussion. In summary, his comments are that it is a book that can be praised for what it does not include as well as for what it does; the NMR section of Chapter 13 provides a clear presentation at a level that most students can handle without venturing into vector modeling; it provides good information on spin system identification and second-order effects, information that is extremely useful when students begin to interpret spectra of common molecules. The book itself has been kept to an attractive and manageable size. I have enjoyed carrying this book around in a way that I would not enjoy carrying around March’s encyclopedic Advanced Organic Chemistry. Students, too, will carry it around and read it. This book can be and should be mastered in its entirety by first-year organic graduate students.
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I spent a lot of time in Chapter 5 (Mechanisms of Organic Reactions) and in Chapter 8 (C⫺C Bond Formation between C⫺Nucleophiles and C⫺Electrophiles). I was especially impressed with the uniquely careful and clear development and illustration of the Hammond Postulate and the Hammett equation. Similarly, the concepts of reactivity are developed in a simple and accurate fashion; in sequence, nucleophilic carbon, electrophilic carbon, reactivity matching, generation of nucleophilic carbon, important specific reactions, including Pd(0) catalyzed C⫺C bond formation and olefin metathesis (Grubbs catalyst). Each chapter ends with a suitable number of study problems at a really good level—not too easy, not too hard, meaningful and accessible to good students. Also, solutions to all of these problems are included at the end of the book. Some instructors may not like this feature, but I do. Serious students at this level know enough not to peek at the answers too soon. Here is a typical good problem: When 17-methyl-5-androstan-3,17-diol [structure given] and its deuterated analog (D at C-3) were tested, it was found that the protio compound is three times more bioactive than the deutero analog. It is also known that the diol itself is not biologically active. What is the likely metabolically active material? Explain.
This is a good problem for students at this level. The problem is new for them and the answer is simple enough. Being able to solve this kind of problem is an important bridge between being an undergraduate and becoming a creative thinker. So, this book deserves to be successful. The author has designed it carefully and extremely well. If I were a first-year graduate student in organic chemistry, I would surely study this book from cover to cover. Literature Cited 1. Daniels, Farrington; Alberty, Robert A. Physical Chemistry, 2nd ed.; John Wiley & Sons: New York, 1961.
Thomas G. Waddell is in the Department of Chemistry, University of Tennessee, Chattanooga, Chattanooga, TN 37403;
[email protected].
Vol. 82 No. 2 February 2005
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Journal of Chemical Education
215
