Chemical Education Today
Organic Chemistry Maitland Jones, Jr. Norton: New York, 1997. xxxiii + 1393 and index. ISBN 0 393 97079 5. $84.95.
At first glance, Maitland Jones’s Organic Chemistry appears to be another in the long list of standard organic texts. The first part of the book is concerned with orbitals and bonding. Then the book moves on to hydrocarbons, stereochemistry, and reactions, following a rather standard functional-group format. It is well worth a closer look, however, because although the format may be standard, the approach is refreshingly different. Jones is concerned not with just the student who is a hard-core chemistry major, but also, as he writes in the preface, with the student who wants a broad yet modern introduction to the subject. To address this audience, Jones has based his text, in large part, on what he describes as a desperate need in organic courses to find generalities. He feels that with the explosion in the amount of material that fits into the course, many students have come to the conclusion that the only way to keep all of this apparently unrelated information together is to memorize it all. Those of us who teach organic recognize that this pathway leads to disaster, so Jones has built his book around the principle that we need to provide a general framework that will make it unnecessary to remember every reaction in a separate category. The general framework that Jones uses is that of Lewis acids reacting with Lewis bases, with an emphasis on the interaction of filled and empty orbitals. Again and again, as you work your way through the text, there are examples of reactions being explained by the overlap of orbitals. Again and again, students see the stabilization imparted by this overlap. As a result of this treatment, it is easier for students to come to the realization that all synthetic processes are merely variations on a theme. Although they still may choose to resort to memorization, at least they are given a well-organized and wellpresented theoretical basis upon which to learn the material. Jones does more than just use a consistent framework throughout the text in an effort to show the interrelated nature of organic chemistry. Repeatedly, he uses examples to set up material that will come later. For instance, the introduction of stereochemistry in Chapter 5 comes directly from a problem posed in Chapter 3. Constantly, throughout the text, phrases such as “we have seen before (p. xxx)” appear, reinforcing the
idea of a common theme. There are other notable attributes of this text. Large red arrows labeled Convention Alert appear whenever one of the numerous conventions of organic chemistry is introduced, and chapters end with a section titled Common Errors, in which many of the standard mistakes are illustrated. Resonance structures are introduced early (in Chapter 1) and curved arrows are used to show how one can go between them. (Resonance is also given an excellent review later in Chapter 9.) Many of the problems in the text are thoughtprovoking, as they are often of the type that requires design of an experiment or explanation of a result. An interesting feature of this text is Chapter 8, Equilibria. Here, Jones gives an excellent review of K, S, G, H, LeChâtelier’s principle, and kinetics as they relate to organic chemistry. He wants students to be aware that although we tend to think of reactions as running from left to right, all reactions are (in principle) equilibria and nature works happily in both directions. After this particular chapter, students should have an excellent grasp of these concepts. If I have any negative comments about the text, most would deal with the amount of material covered, which can be daunting at times. A fairly large number of nonstandard topics are included, such as the E1cB mechanism, Sharpless epoxidation, the Meerwein–Ponndorf–Verley–Oppenauer equilibration, nearly three pages on the Hell–Volhard– Zelinsky reaction, and the Bartlett–Condon–Schneider reaction. As for all texts, however, any material the instructor does not wish to cover can easily be skipped. Although the chapter on Analytical Chemistry is very well put together, the section on 13C NMR is minimal and could be expanded. A CD-ROM containing animations of the orbital interactions would be a useful addition. The comments in the preceding paragraph address minor points, however. In the final analysis, Maitland Jones’s Organic Chemistry is an excellent text. It has a superb focus, a fresh approach and an easy readability that make it worthy of consideration by any organic chemistry instructor. Michael S. Holden Department of Chemistry Dickinson College Carlisle, PA 17013
JChemEd.chem.wisc.edu • Vol. 75 No. 3 March 1998 • Journal of Chemical Education
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