book reviews The text contains a sprinkling of typographical e m s , but the number is not excessive for the first printing of a new text.
The beak is well written and the diagrams well drawn hut the puhlisher has made them so large that only a few fill a page. Mordecai Treblow Mercy Collpge of Detroit Detroit. Michigan 46219
Wilmer K. Fife Indiana UotversRy-Purdue University at Indianapolis Indianapolis. Indiana 46205
Heterocyclic Chemistry Fundamentals of Organic Chemistry
J . A. Joule and G . F. Smith. University
Richard S. Monson and John C. Shelton, California State University, Hay-
ward, California. McGraw-Hill Book Company, New York, 1W20, 1974. viii + 438 pp. Figs. and tables. 17 X 23.5 cm. $10.95. The authors note correctly in their preface, "The study of organic ehemistry con-
tinues to be an important part of the preparation far students in the biological and health sciences." As a small, short book with over generous margins and large print (even for the problems), it should be easily covered in a semester of three lectures per week. While there is not general agreement today on how much and what organic chemistry allied health students need, the book affords probably more than nursing students need, but about the right amount for some medical technology and predental programs. (Premedical and biology students are generally required t o take a full year course of intensive organic chemistry.) Since students pursuing these curriculums usually take an additional course in biochemistry, the inclusion of chapters on carbohydrates, fats and oils, and amino acids and proteins is thought unnecessary when so much valuable organic chemistry needs to be omitted in a short course. The authors expressed intention to include coverage of molecular structure, nomenclature, physical and chemical properties, stereochemistry, and compounds of chemical and biological importance is well conceived and fairly well carried out. I question the extent as well as choice of the coverage of mechanisms in a short course for allied health students. Six pages are spent on Markownikoff addition to olefins, while in the same chapter the authors "adopt the simplifying assumption that carbonium ion rearrangements do not occur." Yet there is mom for only six alkene reactions and S N mechanisms receive only three small pages. Some theoretical concepts could well have been omitted, e.g., hypercanjugation and conformations of alkanes. Optical isomerism is well handled and is approached from the symmetry viewpoint. There is an interesting section on anesthetics in the chapter on ethers. The exercises are numerous and good and generally not too complicated for the short course. The final chapter on spectroscopy seems t o be a useless appendage; if it is included it should be laced near the beeinnine of the book so spkctroscopy's great "se to brganic chemists can be adequately illustrated.
of Manchester. Van Nostrand Reinhold Company, New York, 1972. viii + 361 pp. Figs. and tables. 15.5 X 23.5 cm. $18.95. The appearance of yet another introductory treatment of heterocyclic chemistry, intended far advanced undergraduates and graduate students commencing research, raises two questions: (1) what is the role of heterocyclic chemistry in chemical education; and (2) how well does this new book promise to faster this role, in comparison with other available student texthoaks, such as those of Acheson, Albert, Katritzky with Lagowski, Palmer, and Paquette. As to the first question, Professor Rolf Huisgen has wondered aloud, before the First Heterocyclic Symposium, whether heterocyclic chemistry is not boring. Others have mused whether or not this field is a logical, essential subdivision of modern organic ehemistry. Descriptive heterocyclic chemistry, as presented in textbooks and monographs before 1950, does seem to offer endless vistas of tedium and its empirical insights hardly seemed crucial to the student wishing to master organic chemical principles. Physical organic chemistry, however, has changed these attitudes; mechanistic insights into the apparent alchemy of heterocyclic synthesis and reactivity have largely dispelled the tedium, and have enhanced the scope of electronic principles derivable from a study of this field. As a consequence, modern heterocyclic chemistry has came to merit a place in the chemical curriculum, either as an integrated part of courses on synthesis and mechanism, or as an advanced series of lectures exposing students to multi-functional systems of the most challenging variety. For the latter purpose, a number of textbooks has been written to guide both lecturer and student through the welter of facts that a century of heterocyclic chemical research has accumulated. This brings us to the second question, namely the pedagogic value of this textbook by Joule and Smith. This reviewer was very favorably impressed by: (1) the logical organization of the specific facts; (2) the gradual development of structural and mechanistic principles; (3) the clarity and interrelationships of the explanations; and (4) the judgments on what to omit. In fact, of the existing textbooks, this treatment seems to keep the student most steadily in mind. It does not attempt to be comprehensive or to serve as a reference book.
The level of explanation is truly graduated to the knowledge of the student: the initial chapters offer clear, general discussion of heteroaromatic structure, synthesis, and reactions. These principles are then applied in a detailed manner to the pyridines. Thereupon, the effect of a benzo ring is examined for the cases of quinoline, isoquinoline, and quinolizinium salts, as is the impact of a second ring nitrogen in the three isomeric diazines. Based upon this grounding, further chapters consider the chemical consequences of having positively charged oxygen or sulfur in ammatic rings (pyrylium salts), instead of nitrogen, or of having five-membered, Hiickel-ammatic heterocycles, such as furans, pyrroles, thiophens, azoles, or their benzo derivatives. Within each section on a given heterocyclic nucleus, the essential facts and electronic explanations are marshalled in a consistent, intellectually appealing sequence: occurrence and significance of derivatives of the heterocycle; reactions with electrophilic, oxidizing, nucleophilic, freeradical, end reducing reagents; noteworthy properties of m y , amino, alkyl, carhonyl, and quaternary derivatives; principal syntheses; and examples of multi-step syntheses illustrating current, typical approaches. In realizing this organization, the authors have produced a very effective textbook notable for its clarity, its smooth, readable style, and its lack of factual clutter. Also, the number of factual or typographical errors is pleasingly small. Since the authors are writing primarily for students, the lack of primary literature references is not serious; they have included a fair compilation of existing reviews, monographs, and treatises for further reading. One misses mare keenly any discussion of heterocyclic nomenclature, with which most students need considerable help. In addition, perhaps the time has come to disabuse the chemistry student of the notion that heterocyclic chemists are concerned only with rings containing nitrogen, oxygen, or sulfur. The current literature abounds with rings containing many other metallic or nonmetallic memhers. Finally, although this reviewer agrees with this book's emphasis on heteroaromatic systems, he believes that more discussion would have been useful on such slighted topics as antiaromaticity, pericyelic reaction principles in heterocyclic mechanisms, biogenetic reasoning, and small- and large-membered rings. But these desiderata would only have improved a n already fine book. This book can be strongly recommended as a n excellent textbook for an advanced undergraduate course in heterocyclic chemistry or as a very manageable selfstudy book for a graduate student in chemistry. Professors will want to suggest this book as background reading for a graduate course treating advanced synthetic, mechanistic, and biochemical aspects of heterocyclic chemistry. John J . Eisch State University of New York at Binghamloo Bioghamlon. New York 13901
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