Chemical Education Today
book & media reviews Organic Chemistry: A Comprehensive Degree Text and Source Book, 22nd ed. Hans Beyer (dec.) and Wolfgang Walter. Translated and edited by Douglas Lloyd. Albion: Chichester, England, 1997. xix + 1037 pp. ISBN 1-898563-37-3. $45.00. This work is an English translation of the highly successful German-language Lehrbuch der Organischem Chemie, first published in 1953 and revised through more than twenty subsequent editions. This translation is from the 22nd edition; there was a Spanish translation of the 19th edition and an unauthorized Chinese translation of the 18th. Although the word “Lehrbuch” is usually translated as “textbook”, the coverage of many topics exceeds that in most U.S. textbooks. For instance, the chemistry of cyclobutane and its derivatives extends over four pages and azo dyestuffs (not surprisingly for a text originating in Germany) rate about 12 pages. Structures are clearly and carefully drawn and mechanistic considerations of reactions are usually included where appropriate. The curved arrow notation is used only sporadically throughout the book. Physical properties are included for most individually mentioned compounds. The chapter headings reflect the scope of coverage of organic structures and reactions. They are: 1. General. A survey of laboratory techniques for purification, methods for determination of structure sand a discussion of chemical bonding. 2. Aliphatic Compounds. The longest chapter, covering the spectrum of aliphatic functionality, including main group and transition metal organometallic compounds. 3. Alicyclic Compounds. The emphasis here is on the synthesis of small, medium, large, bicyclic, and spiro ring systems. 4. Carbohydrates. 5. Aromatic Compounds, Derivatives of Benzene. This is the second longest chapter and is focused on the chemistry of substituted benzenes. 6. Isoprenoids. Terpenes and steroids. 7. Heterocyclic Compounds. This chapter covers the many variations of ring size, the identity of the heteroatom, and the number of heteroatoms in the cyclic structure. 8. Amino acids, Peptides and Proteins. 9. The Chemistry and Function of Nucleic Acids. This chapter contains a short but useful discussion of molecular genetics 10. Enzymes. 11. Metabolic Processes. This, the shortest chapter, includes discussions of photosynthesis, fermentation,
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glycolysis, and the citric acid cycle. The book concludes with an extensive appendix of hazardous and carcinogenic organic compounds with their hazard symbols, R numbers (referring to special hazards), and S numbers (referring to safety precautions). The compounds are cross-referenced to the page of the book on which they appear. A second appendix follows with a compendium of named reactions and concepts. Finally, an index of names and a very complete subject index are included. A major emphasis in this text is on the structures and reactions of biomolecules, both synthetic and naturally occurring. This is reflected in the chapter titles mentioned above and in countless examples throughout the text. We learn on page 516 that the amidinohydrazone/thiosemicarbazone derivative of p-benzaquinone is effective as a disinfectant for the mouth and throat and on page 699 that tomatin is a steroid that occurs as an aglycone in the leaves of the wild tomato. Another prevalent theme is the integration of industrial processes with the descriptive chemistry. The section on azo dyestuffs is a significant example, as is the discussion of several methods for the production of acetylene from electrolysis of carbon and hydrogen or methane, hydrolysis of calcium hydride, and plasma cracking of hydrocarbons. The text contains about one reference per page. However, most references are to secondary literature (monographs, serial reviews, and review journals). A frequently cited journal is Angewandte Chemie, and the International Edition in English page citations are given. Most of the literature citations predate 1990, although a few reviews as recent as 1994 were noted. One frustration is that the work of 1500 chemists is cited by name and year of publication, but no journal references are provided. Thus, we read on page 293 that Geuther (1863) first synthesized ethyl acetoacetate and that Geuther and Franklin had a heated argument about the structure. The argument was resolved by Knorr (1911), who suggested a tautomeric equilibrium. This text contains far too much chemistry for an introductory course in organic chemistry. There are no exercises within the chapters and no problems at their end. However, this would be very appropriate as an intermediate text for an advanced undergraduate or beginning graduate survey course in organic chemistry. A student using this book would then have its wealth of information available as a reference for the future. The book can also be recommended for any organic chemist as a first place to turn for information on a compound or a reaction. John C. Cochran Department of Chemistry Colgate University Hamilton, NY 13346
Journal of Chemical Education • Vol. 74 No. 12 December 1997
