Chemical Education Today
Book & Media Reviews
edited by
Edward J. Walsh Allegheny College Meadville, PA 16335
Organic Chemistry by Thomas N. Sorrell University Science Books: Sausalito, CA, 1999. 1472 pp. ISBN 0-935702-47-4. $92. reviewed by Michael S. Holden
For some time now, it has been apparent to those who teach organic chemistry that the primary audience is not aspiring chemists, but rather pre-health students and biology majors. However, the typical organic textbook has not changed to reflect this reality, and the biologically oriented material has been shoved into the last few chapters. This material is rarely (if ever!) reached during the course of the two semesters. As a result, most students who complete an organic sequence have never understood the relevance of the subject to their areas of interest. Some texts have begun to integrate the biologically oriented topics into the text, but Thomas N. Sorrell’s Organic Chemistry has taken this approach to new heights. From the moment you see the cover (a stylized rendition of the citric acid cycle), it is apparent that you are looking at something very different in the world of organic textbooks. Indeed, the preface details the author’s desire to integrate the reactions of metabolic and biosynthetic processes with the typical reactions found in an organic text. If you see no reason to change from the traditional approach to teaching organic chemistry, then you can quit reading right now, because this text is not for you. If, however, you agree with Sorrell that the traditional approach does not work for students whose interests lean toward biology, then you may want to consider this text. First, it must be noted that Sorrell delivers on his promise—there is a lot of biological material in the text, and it all shows up in the sections that cover the chemistry of interest. As a result, in the first half of the book we see multipage treatments of biological SN2 reactions, the possibility of biological E2 processes, and biological oxidation of alcohols. Other biological topics covered early include squalene biosynthesis, allylic oxidation, the cyclic pathway of the arachidonic acid metabolism, and the conversion of lactate to pyruvate (as an example of kinetic resolution). All the biological topics fit nicely into the flow of the text. In the book’s second half, there is much more biological material discussed. The section on Chemistry of the Carbonyl Group contains chemistry of carbohydrates, β -keto acid decarboxylation, biological aldol reactions, biotin-mediated
carboxylations, and fatty acid biosynthesis, among many other biological subjects. Again, this material is incorporated directly into the text, not included as an addendum or “special topic”. The overall result is that the organic chemistry of these processes is apparent, and students are able to see the obvious connection between organic chemistry and biology. Sorrell has arranged the 26 chapters of his text into five parts: Structural Organic Chemistry, Fundamental Reactions of Organic Molecules, Synthetic and Spectroscopic Methods, The Chemistry of the Carbonyl Group, and NitrogenContaining Organic Molecules. Material in the first two parts is what is typically covered in the first half of an organic sequence and the last two parts more or less conform to a standard second half of the course. Part III, Synthetic and Spectroscopic Methods, deserves some mention. Along with treatment of spectroscopic methods, Sorrell includes a chapter on C–C bond formation (this is a wide-ranging chapter that includes main-group and transition-metal organometallic chemistry, retrosynthesis, and protecting groups) and an excellent chapter on asymmetric reactions. Some may argue that the spectroscopic material comes too late in the course, but the chapters are self-contained, and there is no reason that they could not be covered in a different order if desired. My only concern with the text is the amount of material included. At more than 1400 pages, this is a big book, and it is easy to see why—included are many reactions that may go beyond the scope of an introductory organic course. For instance, in this text you will see treatments of the Mitsunobu reaction, TMSI cleavage of ethers, SiO2 and Al2O3 catalysis of HX addition to alkenes, hydroxylamine-O-sulfonic acid– induced conversion of an organoborane to an amine, vanadiummediated epoxidation of allylic alcohols, Raney nickel desulfurization, and the Suzuki reaction. Certainly, all are worthwhile topics, but add significantly to the length and scope of the book. Covering everything included would put us back in the position of not being able to cover a meaningful portion of the biological material because we wouldn't get to the end of the book! Sorrell has produced a unique organic chemistry textbook. He has managed to integrate an enormous amount of biological material into the text and do it in a way that successfully shows the relationship between simple organic reactions and complex biological processes. This approach may well be the “new wave” in organic texts, and Sorrell’s effort deserves a serious look. Michael S. Holden is in the Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896
JChemEd.chem.wisc.edu • Vol. 77 No. 1 January 2000 • Journal of Chemical Education
31
