book reviews An Introduction to Physical Organic Chemistry
Edward M . Kosower, State University of New Yark, Stony Brook. John Wiley & Sons, Inc., New York, 1968. xvi 503 pp. Figs. and tables. 1.5.5 X 23.5 em. $12.95.
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"An Introduction to Physical Organic Chemisbry" presents the elements of mechanism in a broad perspective that will allow the incorporation of new concepts as they are developed. Kosower builds a framework supporting the st,ructure of organic chemistry in a manner that reveals the similarities between snperficially different reactions. The textbook is aimed a t seniors or first year graduate students
with strong backgrounds of undergraduate organic chemistry, preferably the "mechanistic" approach found in Cram & Hammond or Roberts and Caserio, and requires physical chemistry as a prerequisite. The text is divided into three unequal parts dealing with Suhstituent Effects, Medium Effects, and Chemical Intermediates. In the first and longest section, the author discusses t,he relationship of the transition state to the initial state of reactions and develops the semi-empirical mathematical relationships of substituent behavior as applied to polar, radical, and isopolar reactions. Included in this section are excellent discnssions of oharge transfer complexes, and the HoffmannWaodward mles for electrocyclic reactions. Kosower also introduces a useful modification of the Hughes Ingold
notation for more accurately describing and classifying substitution reactions of polar and radical intermediates. The second section introduces the cmcept of solvation, develops the empirical measures of solvent polarity, and concludes by illustrating the effects of solvents (inclading salt effects) on the course of polar and radical reactions. The discussion of the effects of polar aprotic solvents on the rate and conrse of reactions is particularly well written. The final section of the book deals ~ r i m a r i l vwith ~ o l a rand radical interm'ediates and to a'small extent with carbenes. The problem sets a t the end of each chapter are excellent. and are keyed to the original literature making further study and self-correction easy. The problems a t the end of the first (introductory) c h a p ter has the beginning student probe into the tools and conventions of physical organic chemistry b y asking t,hen unanswerable yet thought provoking questions on structure and mechanism precipitating him into the framework of the book. The format of this baok departs from the now classical style of listing reactions by sub-types which is found in Hine and Gould, but rather is an annotated survey of reactions and mechanisms, with pertinent examples from both organic and inorganic chemistry. I n addition the text contains a number of critical and incisive commentaries an some of the current mechanistio problems of interest to the author, which adds much to the value of the book. Although a number of topics such as carbanion chemistry, conformation analysis and stereoehemistry, and steric effects have not been explicitly developed as s e p arate topics, monographs on these subjects are available (and suggested by Kosower) for supplementmy use where desired. A more serious fault, in light of the mixed backgrounds of potential students, is the absence of a detailed chapter on the use and meaning of orbitaleneigy conventions and notation, and molecolar orbital theory which form the basis for manv of the discussions on radical and isopolar reactions. There is mueh in this book that is o u t standing but the many typographical errors both in text and diagrams detract from the clarity of the book. A number of the diagrams were omitted in printing and finding material crassreferenced by section number rather than page is difficult. The clear narrabive style of this baok, with its emphasis on projecting a generalized and unified picture of modes of reaction recommends it to all who have an interest in physical organic chemistry. Since mueh of the material in bhis text i~ not to be found in the older works (Hine, Gould, Ingold, and Ferguson), it can be used either to complement them, or instead of them where a one semester course is desired. HARRYBABAD The 011 Chemical Company Muskegan, Michigan 49945
( C n t i m e d n page A196)
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Journal of Chemical Educafion
