Chemical Education Today
Book & Media Reviews
The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd Edition by Robert B. Grossman Springer: New York, 2003. 354 pages, ISBN 0387954686. $49.95 reviewed by R. W. Holman
And now for something completely different… Well, almost completely different. The Art of Writing Reasonable Organic Reaction Mechanisms is an unusual book in three ways: scope, scale, and style. Excellent textbooks such as those by Lowry and Richardson (1), Carey and Sundberg (2), Carroll (3), and Miller (4) are all classic texts for advanced undergraduate or beginning graduate classes crafted as a survey of physical organic chemistry. They provide an overview of experimental methods for elucidating organic mechanisms and often provide a historic perspective into the development of the field. In contrast, The Art of Writing Reasonable Organic Reaction Mechanisms has an entirely different scope, dedicated to teaching the application of first principles to the construction of organic mechanisms. The emphasis is upon equipping the student with an intuitive sense of how to tackle a complex organic transformation and develop a reasonable mechanism to explain the chemistry. Grossman’s book differs from others in the scale of the worked examples. The number of problems incorporated into the text is extraordinary. The author provides the student a Web site that includes the detailed mechanisms for every problem in the book, each of which includes explanation and commentary, and the answer set, when printed, exceeds 250 pages! In style, The Art of… is unique in that it does not read like a typical textbook. Instead, the feel is like that of having a personal tutor next to you walking you through the chemistry in a step-by-step fashion. The writing is clear, concise, engaging, and, at times, outright entertaining. The lively style includes “Common Error Alerts” that teach students what not to do and includes tips and advice on how to solve problems. Having established the uniqueness of Grossman’s book, I turn to specific content. The author treats the various aspects of reaction mechanisms under six main headings. The Basics section briefly describes the fundamental principles needed to evaluate complex reaction mechanisms. This section has been expanded and entirely reworked from the first edition, and is so well crafted that a student can learn all the essential concepts independently. The next two sections deal with polar reactions under basic and under acidic conditions. The final three sections deal with pericyclic reactions, freeradical reactions, and transition-metal-mediated and -catalyzed reactions. All sections are expertly written, well organized, and up-to-date. The final chapter on metal-mediated chemistry is the highlight of this text, providing a useful introduction to this interfacial area that is so often neglected.
edited by
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
The book’s strengths include the clear style of writing, extensive practice problems, the quality of the mechanistic problems addressed (they come straight from the recent literature), the outstanding answer set available to the students on the Internet, the systematic manner in which concepts are delivered and tested, and the continuity of the problems within each section. The caveats? There is little emphasis on stereochemistry. Apart from this quibble, my biggest qualm is that the answer to every problem in the book is available to the student. Therefore, there are no problems to assign as homework that the student cannot immediately “solve” by going directly to an answer that has been provided. In the next edition, I suggest that a subset of the problems be removed from the answer set so that faculty can use them as assigned homework. The closest text available in scope and purpose is Writing Reaction Mechanisms in Organic Chemistry by Audrey Miller and Philippa Solomon (5). While a very good book in its own right, it does not discuss metal-mediated reactions. The two books are organized differently: Grossman organizes mechanisms by media (reactions in acidic or basic media), whereas Miller and Solomon organize by electrophile–acid and nucleophile–base characteristics. Grossman’s text has a larger number of problems with a greater range of difficulty than the Miller and Solomon text. The ultimate test of a textbook’s value is its applicability in the academic setting. Faculty who teach an advanced undergraduate or beginning graduate course in organic chemistry that does not focus on synthetic methods have a choice. Do we teach a traditional physical organic course or do we focus solely on the writing of reaction mechanisms? The answer depends on what you wish to accomplish. I have long been teaching traditional physical organic chemistry using various editions of each of the texts mentioned at the beginning of this review. The value of the traditional physical organic approach is exposure to a broad array of chemical concepts. This broad exposure is also a weakness in that there is often little time to go into great depth in any one area so that a student might end up familiar with much but master of nothing. The alternative is a highly focused course dedicated to one purpose; developing a student’s skill in proposing reasonable reaction mechanisms. This approach requires sufficient depth of exposure that students develop an intuition about organic reactions. What is the trade off? Breadth of coverage. The focused approach using a text like The Art of… provides no exposure to many of the topics in a traditional physical organic text, such as non-classical ions and linear free energy relationships. So again, the answer depends on what you wish to accomplish. Do you want the breadth of the classic approach or the depth of the focused approach? If you opt for the latter, then the Grossman book is the text of choice. The highest compliment a reviewer can give is to adopt the text that he reviews. The next advanced course I teach will use The Art of Writing Reasonable Reaction Mechanisms with the goal that students will be able to posit a plausible
JChemEd.chem.wisc.edu • Vol. 80 No. 11 November 2003 • Journal of Chemical Education
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Chemical Education Today
Book & Media Reviews mechanism for any new reaction that they encounter. To those of you who have taught traditional physical organic chemistry out of the classic texts, I ask you to consider trying something, well… completely different. The Art of Writing Reasonable Reaction Mechanisms might just change the way you do things. Literature Cited 1. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; New York: Harper & Row, 1987. 2. Carey, F. A.; Sundberg, R. A. Advanced Organic Chemistry, Part
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A, 4th ed.; Kluwer Academic/Plenum Publishers: New York, 2000. 3. Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Brooks/Cole: Pacific Grove, CA, 1997. 4. Miller, B. Advanced Organic Chemistry: Reactions and Mechanisms; Prentice Hall: Upper Saddle River, NJ, 1998. 5. Miller, A.; Solomon, P. H. Writing Reaction Mechanisms in Organic Chemistry; Harcourt/Academic: San Diego, 2000.
R. W. Holman is in the Department of Chemistry, Western Kentucky University, Bowling Green, KY 42101;
[email protected].
Journal of Chemical Education • Vol. 80 No. 11 November 2003 • JChemEd.chem.wisc.edu
