Many of these large sections contain discussions, e.g., on orbital symmetry and crystal field theorv. eood even ,. which are auite .. though rhryare very short. As with m y g o d dirrwnnry, the definitions dostnnd on their own. The value of this kind of book depends, in my opinion, on the quality of the definitions, the inclusion of all appropriate terms, and the ability to find these terms quickly. I think the authors succeeded on all these points. The definitions, especially with the inclusion of the illustrative examples, were a t the very least adequate and most often excellent. I thought of very few terms or concepts that I could not find in the hook, and these were debatably either obscure or of very little interest to most organic chemists. With the aid of the chapter titles, the table of contents for each chaoter. and the index. I also had no difficulty in locating the majority of theterminology quickly. Finally, I should note that the hook contains very few typographical errors and the drawings are first-rate. Richard Pagni me University of Tennessee Knoxville, TN 37916
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Mechanism a n d Theory in Organic Chemistry, S e c o n d ~ d i t i o n Thomas H. Lowry and Kathleen Schueller Richardson. Harper & Row, New York, 1981. x 991 pp. Figs. and tables. 24 X 19 cm.
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This is the second edition of this book, and substantial changes have been made in the format compared to the first edition. Since I have taught a graduate course from the first edition, I find this new version to be well done and a solid improvement. I particularly like the divisions into chapters on aliphatic nucleophilic substitutions since this makes it easier for the transition far a heginning graduate student. Chapter 6 on Carbanions, Carhenes, and Electrophilic Aliphatic Substitution ties together important chemistry in terms of eleetran-rich reacting species. The introduction of perturbation theory and symmetry considerations in Chapter 1 should ease students into this important aspect of modern organic theory. Previously, this material had been placed in a late chapter (Chapter 10) in the first edition. The chapters in the present edition are (1) The Covalent Bond, (2) Some Fundamentals of Physical Organic Chemistry, (3) Acids and Bases, (4) Aliphatic Nucleophilic Substitution, (5) Intramolecular Cationic Rearrangements, (6) Carbanion, Carbenes, and Electrophilie Aliphatic Substitution, (7) Addition and Elimination Reactions, (8) Reactions of Carbonyl Compounds, (9) Radical Reactions, (10) Theory of Pericyclic Reactions, (11) Applications of the Pericyclic Selection Rules, and (12) Photochemistry. This reviewer found Chapters 1 and 2 oartieularlv well done and useful for beeinning graduate studrnrs.'l'he rrnmplesylven ~nChapter 2 1s, iliuslr.ire such phenomena as
proehirality, stereoselectivity, stereospecifieity, eonformational stereoisomerism, etc. are quite good. One cannot expect to include all of the examples that individuals might feel are "favorites," hut most of those included are carried over from the first editian and are reasonably well known to most practicing chemists. The remainder of Chapter 2 is, in my opinion, one of the best in the entire book. This section on linear free energy relationships is a vital one for graduate students and the reading is relatively easy and the data provided is well referenced and up-to-date. Using potential energy surfaces to explain transition state theory will likely not he straightforward for many teaching the first course in mechanistic theory for beginning graduate students hut only the elementary features are given. Chapter 3 on Acids and Bases is much like that in the previous edition. Chapters 4 and 5 have good examples although the reading is somewhat heavier than this reviewer would like. With adequate oral explanation, the material can be both instructive and palatable far new students. Again Chapter 7 is nearly identical with that in the first edition which I found t o be generally acceptable. Additional citations with examples to phase transfer catalysis in this chapter would have been meaningful. Reactions of Carbanyl Compounds (Chapter 8) is also well done for the amount of space devoted to the topic. General catalysis theory and stereochemistry of the addition processes serve to lay the foundation for the chapter. The chemistry of earhoxylic acid derivatives as well as that of enolates is discussed. This reviewer would have preferred additional details of enamines which are sueh valuable intermediates. Chapter 9 on Radical Reactions appears to have undergone some usefill changes compared to that in the first edition. Better examples sueh as for the generation of biradicals as given in eqn. 9.34 (p. fi93) are included and illustrate the stereochemical aspects t o the process. Appendix 1 t o this Chapter on CIDNP is a useful addition, in my opinion. In Chapter 10, perieyclie reactions are discussed in detail, but the foundation has been laid in Chapter 1. In Chapter 11, the applications of the selection rules follow in logicdl fashion. Not only are the data well referenced in each chapter, hut also the discussion is lucid, and those unskilled in the use of the selection rules will find the discussion enlightening in both chapters. The correlation diagrams in the latter part of Chapter 10 are easy to follow although the symmetry considerations must be envisioned quickly in order to comprehend the operations. This reviewer found the examples in Chapter 11to he well chosen. Chapter 12 on Photochemistry is very similar to that in the first edition. The discilssion on cis-trans isomerism appeared to be an improvement over that given in the first version. By expanding the description of Norrish Type I1 reactions t o include correlation diagrams, the reader is better able to comprehend in a logicalmanner the chemistry which occurs. In summary, this second edition should serve as an excellent aid to first-year graduate students and to all of those who wish t o upgrade a physical organic chemistry course to a modern approach. Moreover, it will also he a valuable reference for any organic
chemist's library.
K. Darrell Berlin Oklahoma Sfate University Stillwater, OK 74078 Introduction t o Organic Chemistry, S e c o n d Edition Andrew Streitwieser and Clayton H. Heathcock, Macmillan Publishing Co., New York. 1981. xxii 1258 pp. Figs. and tables. 18.5 X 24 cm. $28.95.
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The second edition of this important textbook appears on the market about five wars after the first edition was introduced.
result is an improvement on what was already a very fine introductory textbook. The authors have obviously been responsive to suggestions from their users and have modified some of their earlier innovations (e.g., the very early introduction of organometallic chemistry) without sacrificing the rational development of their teat or compromising the pedagogical philosophy behind it. That philosophy is to develop the student's understanding of organic chemistry topic by topic, one functional group a t a time, in contrast to the alternative strategy of progressive repetition. Since the treatment is quite thorough, some of the chapters are a good deal more detailed than those in competing first year organic tab. As a result it prohahly will be a useful reference book far many students long after they have completed their first year of organic chemistry. When the first edition was reviewed by G. 0. Soessard of St. Olaf Colleee for THIS many of its potential users. Since it had been introduced as a real alternative to the well proven and very popular Morrison and Boyd text, there were reasonable doubts whether Streitwieser and Heathcock would be "teachshle" to most undereraduate chemistrv
required before the strengths and weaknesses of a new textbook are revealed in the classroom. By this time a considerable body of experience in the field suooorts the use of the
used it for a year in an honors class a t the University of Pittsburgh, after much enthusiastic previous experience with Morrison and Boyd and can report general satisfaction by teacher and students. I believe that a major factor in this success is the clarity and care of the authors' presentation. Having rejected the progressive repetition approach, they are required to help the student "get it right the first time" and every effort has been made to achieve this end. The strong points of the first edition have been improved in the light of pedagogical experience. A bolder face of type makes a strong impression on the eye and presumably will show through the inevitable layers of yellow overlining which will be provided by the student. The valuable use of stereoscopic (Continued on page A144)
Volume 59
Number 4
April 1982
A143
