book reviews end of each experiment. Although the manual has few serious flaws, some minor criticism is in order. The discussion of laboratory safety (Ch. 1) does not mention the necessity of wearing ?hoes in lah. In our experience the sulfanilamide experiment (Ch. 14) is tricky, results are variable, and, if the experiment is to be done, it should be started at the N-acetylsulfanilyl chloride stage. The use of chlorosulfonic acid is dangerous and unnecessary: there are far safer experiments for illustrating electrophilic aromatic substitution. The alkyl halide experiment (Ch. 10) works well, but the instructor's manual should include a nate that the acetone used in preparation of the NaI in acetone solutions must be absolutely dry for good results. I t is hest to prepare fresh solutions each day. A final bone to pick is the author's frequent use of non-metric units. If these are to be used, the metric equivalent should also he included. Gayl H. Wiegand Idaho Smte University WcateWo. !dab 83209
Laboratory Praotlce of Organlc Chemistry. Fifth Edltlon Thomas L. Jacobs, University of California, Los Angeles, William E. Truce, Purdue University, G.Ross Robertson, Late of the University of California, Lw Angeles. Macmillan Publishing Co., Inc., 463 pp. Figs. and New York, 1974. x tables. 21 X 24 cm. $10.95.
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The current edition of this organic lahoratary manual is the evolutionary product of the manual first authored by the late Professor Robertson in 1937. As such, it retains the somewhat unique feature of presenting theory and techniques of organic laboratory preparations in Part 1 (Theory and General Practice, 190 pp.), while presenting the actual experiments in Part 2 (Lahoratory Experiments). Individual sections are again numbered sequentially throughout the entire hook, enabling appropriate cross references to be made by section number. This edition has typeset which is easier to read than in previous editions. I t is generally free of errors. Chapters 1-8 and 12 are little changed from those found in the fourth edition.' Chapter 9 (Extraction, Adsorption, and Chromatography) now contains brief, but useful, sections on vapor phase and thinlayer chromatography. Chapter 10 (Drying of Organic Preparations) now contains a useful table of common drvinr aeents and a * discwsiun of the use of molrrular siwes. Chapter 11 (Sdvents and Solubility) has been rewritten to make it more readable and now includes short discussions of solvent effects on organic reactivity and the use of dipolar aprotic solvents. Chapters 14 (The Literature of Organic Chemistry) and 15 (Writing a Research Report) have been extensively revised and updated to include contemporary organic literature sources. The only completely new portion of Part 1 in this edition is found in Chapter 13 (Spectroscopic Techniques). This chapter ~~
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provides only very brief coverage of infrared (9 pp.) and nuclear magnetic resonance (6 pp.) spectroscopy. Ultraviolet spectroscopy and mass spectrometry are not discussed a t all, although numerous references are given to more complete literature sources dealing both generally and specifically with ir, nmr, uv, and ms teehniques. Because the material in this chapter is of such restricted scope and depth, it seems likely that the value of the chapter will he limited to the use of the concise tables of functional group ir absorptions and nmr chemical shifts by students who have previously acquired an understanding of the basic spectroscopic techniques. From an instructor's point of view, Part 2 is the most desirable feature of this manual because of the extreme flexibility with which it may be used in the lab. As before, it contains a number of experiments, many of them new (e.g., the Wittig reaction), as well as a eonsiderablv revised.. exoanded. and updated ieetion on qualitative wganie analysis. Although 4 1 "experiments" are listed, many actually contain reveral experiments in the form of options in the treatment of the same chemical phenomena or alternative reaction sequences. For eaample, Experiment 24 deals with carbanions and offers such options as aldol, crossed aldol, Perkin, Claisen, and Dieckmann condensations as well as a haloform reaction. With this manual, it would he very easy far an instructor to have different students in the class performing different operations a t the same time. The degree to whieh the experimental directions are explicit is quite variable and the student may frequently have to refer to sections in Part 1in order to balance equations, calculate quantities, understand techniques, etc. Potential hazards are clearly identified. This is definitely not a "cookbook." The student with a desire to learn and enjoy the theory and practice of organic laboratory operations should receive this manual with enthusiasm; hawever, the student who prefers to be led in every detail will likely experience frustration on occasion. The final section of this manual (Special Experiments) consists of an updated comnilation of references to some 75 eaoerimcnw from the literature which emphasize special techniques or reagents. It should be mentioned that, with the exception of some of the experiments in this last section and several of the regular experiments for which ir and umr spectra of reactants and products have been provided, there has been no attemot made to incoroorate nmr. ir, or vpr techniques into the rxperiments. On halnnre, this manual suffers some of the unevenness encountered with a book which has undergone so many revisions;, however, it has sufficient strengths that it merits serious consideration by any instructor who wishes to teach a flexible laboratory course in whieh students work with their heads as well as their hands. ~
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'Reviewed by Gregg, D. C., J. CHEM EDUC.. 40.106 (1963). James L. Fry The UnIyBrsW of Toledo ToWo, Ohio 43606
Interpretation of Infrared Spectra. An Audlo-Vlsual Programme J . H. "on der Moas, Heyden and Sans, Ltd., London, 1974. 4 tape cassettes; 123 slides. $120 This title consists of an audio-visual (four tape cassettes-123 slides) introduction to the interpretation of the infrared spectra of organic molecules and organic functional groups. The program consists of eight lessons, each containing between 12 and 20 slides and a 15-minute tape discussion. T o allow for etudent feedback during the presentation, the student is provided with a course book in which he answers questions posed by the narrator. Each student is also provided with a blank Colthup Table to be filled in as he encounters new information on the relationship of structure to the infrared absorption frequency during the course of the program. The course is rather narrow in scope, covering the infrared frequencies of organic functional groups in the 4000-650 cm-' range (the micron scale is not used or even mentioned). The usual Litany of organic functional groups (olefins, acetylenes, aromatics, esters, aldehydes, nitriles, acids, etc.) are covered and examples with simple organic molecules are provided. However, nothing is said ahout the near or far infrared regions and their utility in structural or functional group determination. T h e use of infrared spectroscopy in the study of organo metsllie or inorganic complexes is not covered either, and virtually no theory is included. However, within the scope of the program, the material is very well presented and provides a quick and direct introduction to the topic. I t should he useful as a mechanism for introducing undergraduates and technicians to this spectroscopic technique in s self-paced learning situation. Victor J. Hwby
university of Arizona Tucson, Arizona 85721
Chemlcal ReactlvHy and Reactlon Paths Edited by Gilles Klopman, Case Western Reserve University, Cleveland, Ohio. John Wiley & Sons, Inc., 1974. 369 pp. Figs. and tables. 16 X 23.5 cm. $19.95.
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This book is of the tvne which the instructor of an advanced yhysical-organic course may well wish to put on reserve. I t should alsr, be of ronsidernhle d u e ru the practicing organic chemist, either in an industrial or academic environment, who feels somewhat out of touch with modern theories of organic reaction mechanisms. However, as is usually the case with a collection of contributions from several authors, it cannot be recommended as a primary textbook. On the dustcover, it is claimed that the book would be worthwhile for both organic and inorganic chemists interested in the logic behind the mechanisms of chemical reactions. However. the examnles used to illustrate the principles under discurrion are almost exclusively from the realm of or. ~
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gsnic chemistry and all of the contributions are definitely addressed to the organic chemist. A phenyl group is missing from the acridinium ion within the equation on page 225, but the book is in general free from errors. Of the 13 chapters, one is an introduction by the editor and the others are each by different authors, including a further contribution by the editor. Indeed, slightly over one-half of the book is occupied by just two chapters: the second chapter by G. Klopman (The General Perturbation Theory of Chemical Reactivity and Its Applications), occupying 112 pages, and an 86 page chapter by R. F. Hudson (Nucleophilie Reactivity). Fortunately, hoth of these are well written and can he recommended as good general reviews of their respective topics. The chapter by G . A. Olah (22 pages) entitled "Electrophilic Reactions: The General Concept of Carbocations and Their Role in Electrophilic Reactions of Alkanes (o bases)" is well worth reading but its value is diminished somewhat by the lecture upan which it is based having previously been reported a t some length in Chemistry in Britain. The chapter "Intermolecular Interactions and Chemical Reactivity" (32 pages) by H. Fujimoto and K. Fukui can be recommended for the reader unfamiliar with the concepts of HOMO, LUMO, and frontier orbitals. The underlying theory is, however, presented only in considerably condensed form. The intent of the other chapters varies from a collection of abstracts of assorted studies from the laboratories of the author, so brief as to be of limited value except ss a source of references, to a 24 page cantrihution (with 123 references) by five coauthors. which is more in the nature of a research contribution; in this chapter, the reader reaches reference 30 within the first short paragraph! Dennis N. Kevill Nwthem Illinois University DeKalb. lllinos 60 115
Molecular Reactlon Dynarnlcs
R. D. Leuine, Hebrew University, Jerusalem and R. B. Bernstein, University of Texas, Austin, Texas. Oxford University Press, New York, 1974. vi 250 pp. Figs and tables. 16 X 23.5 cm. $10.
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The problem of understanding the mechanisms and rates of chemical reaetions in terms of the dynamics of molecular encounters has been of interest to chemists for many decades. Initial progress in this area was slow mainly due to the difficulty of obtaining information about the details of pair-wise molecular collisions from either experimental or theoretical studies. Recent advances on hoth of these fronts have led ro n dramatic accelemtion of prop,. ress m this area, and although rhar pnrgresr IS well ducumented m n plerhura of research papers, review articles, and specialized monographs, there has developed a need for a state of the art survey of the entire discipline in which the relationships between the many diverse subtopics is clearly shown.
I t is appropriate that scientists who have clearly established themselves as leaders in the field should undertake the project. This book is the result of collaboration between two such men. Levine and Bernstein have written an elementary text intended to be a primer in the field of molecular reaction dynamics and useful to students with a minimal training through the underaraduate ohvsical ehemistrv level. The rbook contains 30 sections divided among six chapters. Each section covers sufficient material to comprise the basis of a single class meeting, so the hook is well suited for USC in a one term course. Passages dealing with technical material of more complexity thnn rhnt of the main body of the hook arc designated by asterisks sothat they may be skipped, if necessary, to accommodate a quicker survey. Appendices are introduced as chapter sections in the body of the text as needed. These too may be skipped by the cursory reader but will prove of substantial value,to the serious student. A bibliography is included for each section providing a guide to the literature relevant to the section topic. The index is extensive so that finding specific information is straightforward. Being based on the experiences of the authors gained from teaching such courses over a period of several years, the material is for the most part well ordered. The student is led sequentially from an introduetian to the dynamics of collisions between structureless particles to consideration of collisions between polyatomic molecules with emphasis on the many modes of energy transfer available to the systems. The relationships between molecular dynamics and bulk kinetic parameters are explained. Methods used to auantifv oarameters of speclfic interactions arc introduced along the was as required. 'Thee include molecw lar hrnm rerhniquer, time resolved spectroscopy, double-resonance methods, photo-fragment spectroscopy, ehemiluminescence, and calculated potential energy surfaces. The final chapter includes a case history, to date, of what has been learned by application of the available tools to probe the dynamics of a single reaction: F +Hz=HF+H. The style of writing is rather casual which in itself is not objectionable but is, in fact, a rather refreshing change from the cold formality of many science texts. The quality of the work is, however, diminished on occasion when that casualness influences the orderly organization of material and the definition of terms and symbols. The latter problem is compounded by the inclusion of many figures reproduced from the literature. Occasionally the notation of the figure does not agree with that of the text, or one or more symbols are not defined either in the caption or in the text. The meanings can usually he inferred from context and at times subsequent sections help clarify previous ones. Students for whom the subject matter is largely new would do well to read through the text twice; it is short enough to permit this with ease even in a single term. Perhaps the most serious shortcoming of the book, however, is the absence of any problem sets. This greatly reduces its effectiveness as a teaching instrument and is
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(Continued on page A388) Volume 52,Number 8, August 1975 / A387
