Chemical Education Today
Book & Media Reviews Organic Chemistry, 2nd Edition Paula Y. Bruice. Prentice Hall: Englewood Cliffs, NJ, 1998, xxx +1256 pp, 6 appendices. ISBN 0-13-841925-6. $99.
The author has made some constructive changes to the second edition of this visually pleasing book. The chapter order has been rearranged so that all of spectroscopy is covered in two adjoining chapters (new problems combining NMR and IR have been added), all of the chapters on bioorganic chemistry are grouped together (information on reducing sugars has been added), and the last section now covers heterocycles, pericyclic reactions, polymer synthesis, multistep synthetic strategies, and drug design. The publisher offers additional material at its Web site and a paperback for students assisting them in using the Internet. The ChemCentral Organic Web site has problem sets to supplement each chapter (including hints for struggling students) and animations of molecules undergoing reactions. In addition the Web site provides syllabus construction software for instructors. The accompanying study guide/solutions manual, written by the textbook author, contains a glossary, answers to chapter problems, and a practice test (for the first twenty chapters). There are sections called “special topics” which offer in-depth treatment of pH, pKa, buffers, and the electron-pushing formalism. There is a strong bioorganic emphasis in this text. Many of the examples given to illustrate chemical and physical properties are biomolecules or drugs. After explaining catalytic hydrogenation of alkenes, reference is made to reduction of alkenes found in the Krebs cycle. When the reactivity of epoxides is presented, it is followed by a discussion of the helpful and harmful actions of arene oxides in living systems. The section on amide hydrolysis is followed by an example showing how enzyme-catalyzed amide hydrolysis is the mode of action by which penicillin inhibits bacterial cell wall synthesis. Structures for ten variants of penicillin are illustrated with a brief discussion of the relationship between structure, bacterial specificity, and antibiotic resistance. This extensive treatment of bioorganic chemistry would make this textbook a good choice for those teaching budding health-care professionals. As an alternative to the traditional functional group organization found in most introductory organic chemistry textbooks this author has elected to explain a common mechanism by grouping together similar reactions of different functional groups. Using this organization she hopes to promote greater understanding while discouraging rote learning. For example, three chapters are used to discuss nucleophilic substitution and elimination. The first is a standard treatment of substitution in alkyl halides; the second introduces elimination, again in alkyl halides; and the third treats substitution and elimination in alcohols, ethers, epoxides, organometallics, thiols, and amines. Another example of this mechanistic grouping is the section devoted to carbonyl chemistry. The first chapter introduces nucleophilic acyl substitution of carboxylic acids and their derivatives with oxygen and nitrogen nucleophiles; the second introduces nucleophilic addition to carbonyl carbons by carbon, hydrogen, oxygen, and nitrogen nucleophiles, the third covers all redox reactions, and the fourth explains the reactions of the alpha carbon. This mechanistic grouping has been attempted by several authors, including Fox and Whitesell in their recent book. While this organization may not appeal to all, I believe the clarity and streamlining of carbonyl chemistry section is very effective. Traditional functional group organization with preparations and reactions of each carbonyl compound being given separate chapters becomes excessively repetitive. Bruice does not include preparation reactions for each functional group separate from its reactions. She does, however, provide an indexed appendix that allows one to locate a particular functional group preparation with ease. Some of the strengths of this textbook are the number of examples given, especially with respect to IUPAC nomenclature; interesting analogies and illustrations; good-end-of-chapter summaries, with key terms indexed to pages in the chapter; interesting biographical information in the margins near the introduction of the chemist’s contribution; extensive use of electron-pushing arrows to show how reactions occur; and early introduction of multistep synthesis and retrosynthetic methods. There are, however, some sections in which the writing is unclear. An example of this is the treatment of the Hammond postulate. Overall, I think this bioorganic approach will work well for students interested in the life sciences and in health care fields. Marlene Katz St. Louis College of Pharmacy St. Louis, MO 63110
1390
Journal of Chemical Education • Vol. 75 No. 11 November 1998 • JChemEd.chem.wisc.edu
