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The organic instructor asks many questions of a new textbook: "Do I like what's in and what's out?" "Can I base my course on it?" "Will my students lift it, read it, and understand it?" "Is it better than the book I have been using?" William Brown's new textbook probably will be adopted widely because the answers to these questions will be positive for many instructors.
Brown has used a traditional format, with which most instructors and students feel comfortable, organized by functional group with extra chapters for acid-base, stereochemistry, and spectroscopy. The written presentation of the material is clear and precise, but the feature that makes the book unique is the powerful stereoscopic artwork that is far superior to any textbook on this level that I have seen. Stereo drawings are seen through a viewer (attached to the cover) to give remarkable three-dimensional presentations of proteins, steroids, and other complex biological molecules, as well as transition states and molecules of theoretical significance. These stereo views are much better than models for the student because they can show structures that are too complex for simple model kits, and because they can show conformations that are difficult to construct. Particularly impressive are the portrayals of a hemicarcerand that is used to isolate cyclobutadiene, the Bergman reaction in biological systems, and two cyclization reactions that test the steric requirement for SN2 reactions. However, the stereo views are not limited to especially complex structures but also are useful for showing the conformations of simple alkanes and cycloalkanes and configurations of chiral molecules.
Unfortunately, the rest of the artwork is disappointing. A large number of photographs give the pages a certain visual interest but do not help in understanding chemistry. For example, there are many plant and animal pictures that illustrate the sources of natural products and several pictures of various chemical plants with very tall towers. There is a butane lighter and a gasoline pump, and bottles of vitamins, nail polish, and vinegar. These illustrations may belong in high school textbooks, but they seem to be out of place here. Another source of annoyance is the overused color "highlighting" of reactions, to show how the products are derived. The colors of the highlighting are apparently random: a table of alkene addition reactions shows six electrophilic reagents, each in a different color, and the gold bromination in the table is mauve two pages later, along with a turquoise chlorination.
Superfluous coloring is used for cycloalkanes, that appear as brightly colored polygons, steroids, which contain four different colored rings, and spectra, that have uniquely colored backgrounds. (I did enjoy the diagram of the Dean-Stark trap (Fig. 17.6), that is presented with clarity and wit.)
The written presentation, as noted above, is excellent. Brown is able to present concepts lucidly and directly. I appreciated his treatment of such diverse topics as the IUPAC rules for naming alkanes, the relative nucleophilicity of halide ions in protic and aprotic solvents, and the behavior of halogen substituents in electrophilic aromatic substitution. The directions for solving spectroscopic problems are clear and useful. There are some chemical (and historical) errors, to be sure, but these are too minor to be mentioned. The problems are plentiful and appropriate; those at the end of the chapter are grouped by subject. Especially useful are the "applied" problems, labeled with a tetrahedron, which involve a natural product or a synthetic pharmaceutical.
Some topics in other books are not covered here, for example, combustion analysis, pericyclic reactions, or synthesis as a unified, separate chapter. A chapter on synthetic polymers by Bruce M. Novak, printed as a supplemental paperback, will be included with the book but was not available for this review.
Throughout the text, short supplemental essays called "Chemistry in Action" appear in boxes. Brown acknowledges in the preface that the majority of these essays were written by J. William Suggs, and he deserves more prominent mention for his contribution. Supplemental essays are not new with this text, but the topics here, on industrial, pharmaceutical, and biological organic chemistry are especially well chosen and brilliantly done.
Finally, there are interviews called "A Conversation with. . ." Carl Djerassi, Roald Hoffmann, Jacqueline K. Barton, and Siegfried Reich. Each tells about her/his career and accomplishments, motivations, and general outlook as a chemist. The jacket tells us that these interviews "humanize the subject". However, I also had a conversation with Roald Hoffmann in Spring 1993, and he told me that his general chemistry students did not want their course to be humanized, as he wished, but rather to be more oriented to the MCAT exam. Perhaps there are some students who will read the essays in Brown's book and appreciate that organic chemistry is an exciting career choice as well as a required premed subject.
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