Chemical Education Today edited by
book & media reviews
Edward J. Walsh Allegheny College Meadville, PA 16335
Organic Chemistry, 2nd ed. Marye Anne Fox and James K. Whitesell. Jones and Bartlett: Sudbury, MA, 1997, ISBN 0-7637-0178-5. $83.75. and Core Organic Chemistry (abbreviated edition) Marye Anne Fox and James K. Whitesell. Jones and Bartlett: Sudbury, MA, 1997, ISBN 0-7637-0367-2. $68.75. Casablanca; Star Wars; Independence Day; Morrison & Boyd; Solomons; McMurry. Blockbusters all. Now, the improved second edition of Fox and Whitesell, Organic Chemistry, has entered the somewhat crowded theater of textbooks available for use in a serious course of organic chemistry. Does it warrant consideration for recognition within the previously mentioned pantheon? It just might. Some decades ago, Cram and Hammond recognized the value of an introductory organic text developed around the structure/mechanism format, but it and its multiauthored successors were unable to muscle out those texts nominally built around the study of functional groups. Still, for many of us, the more logical, clarifying, and satisfying approach to teaching organic uses structural features and reaction mechanisms to bring better order and linkages to the overwhelming amount of information available in our course. Fox and Whitesell revived the Cram and Hammond format, modernized it, acknowledged by emphasis on the bioorganic the real “customers”, and delivered a textbook in 1994. (See review by Samuel Levine, J. Chem. Educ. 1994, 71, A261.) In short order, a second edition of this primary text has been published as well as the first edition of an abbreviated version. As in the earlier edition, the authors have streamlined the “core” material presented to fewer than 850 pages (includes summaries, reviews, and problems). Nothing omitted from the typical organic textbook fare is likely to be missed. This core material is organized into 16 chapters. The first five introduce structural theory, including stereochemistry, and spectroscopy. Chapters 6–13 coherently present theory based on type of reaction—addition, elimination, substitution—and type of reaction species— carbocation, carbanion, radical. The final three chapters within the independently available core discuss the special topics of skeletal rearrangement, multistep synthesis, and polymers. As suggested, this 16-chapter text is available as Core Organic Chemistry. Beyond this core are seven additional “stand-alone” chapters that can be purchased individually or the entire 23-chapter text can be purchased as Organic Chemistry, 2nd edition. These seven well-presented special-topics chapters focus on subjects such as naturally occurring oxygen-continuing compounds, catalyzed reactions, and the molecular basis for drug action, and each is either 32 or 48 pages in length. In addition to either of these two texts, a group of ancillary materials is available, among them the expected Study Guide and Solutions Manual. Included gratis with either text is a CD-ROM entitled Chemistry in Motion, and noted within the text are the reference points where this CD-ROM offers guidance. Also, relevantly referenced in the text is the use of a separately available CD-ROM set, CHEM-TV. Organic Chemistry I and II. The book features the extensive, integrated use of line drawings for structure representation, curved arrows for electron movement, and energy considerations for chemi-
cal reactivity explanations. Spectroscopy is presented early in the text and is used sparingly, though usefully, afterwards. Space-filling models for molecular structure are used throughout, although I found them often more decorative than instructive. The Chemistry in Motion CD-ROM colorfully displays many of the complex molecules as well as mechanistic and conformational details, but the depictions fell short of my expectation. The book contains a superior set of problems, presented as exercises within the chapter and as review and supplemental problems at chapter’s end. The Study Guide gives answers, with useful associated narrative, to the exercises and review, but not the supplemental, problems. Each chapter concludes with a summary and reaction review as needed. From time to time, collections of reactions and synthetic methods are compiled as tables, and the appendix includes a synthetic method summary and glossary of terms. In the beginning of the preface, the authors bluntly reveal what we already know. Many students find organic chemistry a daunting experience and, when they cannot locate its relevance to their academic life, even suggest that it’s boring, a jumble of memorization. By structuring the subject matter differently, trimming unneeded information, regularly cross-referencing and summarizing, and frequently presenting examples from the commercial and the bioorganic worlds, the authors have attempted to counter the criticism. However, without bringing some personal viewpoint to a book review, usually guided by thoughtful subjectivity, a reviewer does little more than provide information readily obtained from the publisher’s advertising. With that backdrop, my assessment of the strengths and weaknesses of the Fox and Whitesell text proceeds. For me, the crowning asset of this work is its approach and concept organization; it arranges organic chemistry in a pedagogically sound manner. The writing is efficient and generally quite clear. Humor even appears, primarily in the excellent brief but numerous “chemical perspectives” insets included throughout the text. On occasion (somewhat surprisingly for this tightly worded text), detailed explanations, usually of associated diagrams, become tiresome and a few chapter openings sputter with unnecessary repetition. For a book with so much content, only a few errors were noted, and those may be corrected in subsequent printings. I perused this text at a far more rapid clip than would a student, which resulted in two general impressions that might not transfer from a more leisurely reading. Though the basic content is presented clearly and supported by timely examples, the pace is relentless. Classroom and tutorial sessions have great potential for relevance and usefulness, especially in conveying some sense of discovery that the text lacks. The metaphor of organic chemistry as a holiday feast surfaced on more than one occasion. As the pages turned, the ingredients were being assembled, the recipes referenced, and some dishes prepared, with the promise of a later, fulfilling meal. But my hunger needs were more immediate. It takes over 300 pages, 40% of the core text, before chemical reactions and mechanisms are discussed in detail—before nibbling can occur. Acknowledging that mechanistic theory is supported logically by structural understandings, chemical reactivity is too important to postpone. Subjectivity exposed. Concerns notwithstanding, Fox and Whitesell have cre-
Vol. 74 No. 9 September 1997 • Journal of Chemical Education
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Chemical Education Today
book & media reviews ated an impressive alternative to the recent traditions of organic textbooks, using an approach that merits serious consideration. It remains for those of us who teach organic how best to use this valuable addition to the marketplace. Samuel S. Stradling St. Lawrence University Canton, NY 13617
