sufficient detail to enable the students to do the experiment while in the others the students can follow thwdescription of the experimental procedure and do the suggested cdculations. Occasionally, the Editor: W. F. KIEFFER students will have to obtain information from the literature to do the open-end College of Wooster experiment. In all experiments, the sugWmter, Ohio gested open-end experiment is a logical and meaningful extension. Some of the suggested open-end operations involve the use of s. simple spectrophotometer and several could involve the use of a pH meter. The more able students should any of the material he is reading, could find the open-end experiments to be chalget out of this survey is another question. Ienaiag nnd intcrviting. The twenty-seven page index is an inT w o exprrim~ntrthat appeared in the dication of the number of terms encounRdwfir-r edition have bran elimlrl.31~~: -tered. tion of Oxides, Law of Multiple ProporIn the lists of suggested readings a t the tions; and Chemical Kinetics, Rate of end of chapters are many references to Reaction of Hydrogen Peroxide with articles in THIS JOURNAL but the inIodide Ian. Three new experiments have clusion of rather large and somewhat been added to the second edition: Theradvanced texts without suggesting a t mal Analysis, Phase Diagram for a Binary least specific chapters seems of questionSystem; Chemical Kinetics, Rate of able value to the students for whom this Reaction of Peroxydisulfate Ion with textbook is written. Many of the quesIodide Ion; and, The Behavior of Metal tions at the end of chaoters seem auite Ions in Solution, Ion Detection. A Brief Section on Elementary Geometric Formulas, a. Table giving Density and Atomic Radius of Metals, a section on the operaM. P. PUTERBAUGE tion of a pH meter, and a section on the Ashland College operation of a spectrophotometer are Ashland, Ohio 44805 included. With theexception of the addition of the section on open-end experiments, only minor changes, if any, have been made. The descriptive sections, experimental procedure, data. sheets, and questions General Chemistry Laboratory remain essentially unchanged. The second Operations edition is appreciably mare expensive than R. Stuart Tobias, Purdue University, the first. Lawrace E. Conroy, and Robert C. This second edition should be very us% Brasled, both of University of Minneful to those individurtls searching for a sots, Minneapolis. 2nd Ed. The collection of well-written experiments of a MacmiUan Company, New York, 1971. quantitative nature that emphasize chemi255 pp. Figs. and tables. 28 X x cal conceots. Theintroduction of the use 22 cm. $5.50. of in4runlmtstion iu sonlr of the opeuend experimruts ra n n nrtrar~ivefwtuw of The authors have improved decidedly the manual. this second edition [see THIS JOURNAL 42, 578 (1965)l by add'ing s. section entitled H. A. N E I O I ~ "open-end experiments" to eighteen of the Lebanon Valley College twenty-two experiments appearing in the Anndle, Pennsylvania 17WS labboretory manual. Ahout half of the open-end experiments are presented in
book reviews
Essentials of Geneml, Organic, and Biorhemistry
Joseph I . Rrmth, Darrell P. Eyman, and Donald J . Burton, all of the University of Iowa, Iowa City. W. B. Smnders Co., Philadelphia, 1969. X 718 pp. Figs. and tables. 17.5 X 25.5 em. $9.95.
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The authors indicate this text is d e signed for students "desiring a oneyear exposure to the field of chemistry to prepare them for other professions or to increase their knowledge and understanding of current developments in chemical research." They planned to "include a. balance between a brief historical development, the essential d e scriptive material, and the mechanism of chemicd reactions in general, organic, and biological chemistry" and offer the hook as s survey of these fields. Any attempt to follow as hroad a program as the authors suggest would doubtless invite criticism a t every tumchoice of topics covered, depth of coverage, too much or too little mechanism, d e scription, and theory. To focus on one small point, for example, one finds in the only chrtpter on metals covering all representative and transition metals complete with coordination compounds that in the total of twenty-seven pages about five of them are devoted to iron metallurgy with blast furnace, Bessemer, and open hearth processes all intact. Certainly a trained chemist going through a book like this as his eye catches flashes of term after t e r n will probably subconsciously add his own understanding of them. But what a student, bringing with him very little prior knowledge of
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Organic Chemistry: Methane to Macromolecules
-Reviewed in this Issue
John D. Roberts, California. Institute of Technology, Ross Stmart, University of British Columbis, and Marjorie C. Caserio, University' of Crtlifornia, a t Irvine. W. A. Benjamin, he., New 840 pp. 15.9 X York, 1971. xiv 60.2 cm. $15.95.
Joseph I . Routh, Darrell P . Eynan, and Donald J . B u m , Essentials of General, . . .A501 Organic, and Biochemistry R. Stuart Tobias, Lawrace E. Conroy, and Robert C . Brasted, General Chemistry . . .A501 Laboratory Operations John D . Robwts, Ross Stewart, and Ma+ie Methane to Macromolecules
C. Caserio, Organic Chemistry: . . .A501
Hmvard D. Weiss, Guide to Organic Reactions Otto Theodor Benfey, Introduction to Organic Reaction Mechanisms Louis P . Hammett, Physical Organic Chemistry
. . .A502 . . .A504 . . .A504
Minoru T~utsui,M m i s N . Lay, A k i ~ aNakamura, and M i t w Ichikawa, . . .A504 Introduction to Metal r-Complex Chemistry . .A506 New Volumes in Continuing Series
.
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The revision of this well-established text is similar in many respects to the fine first edition. Although substantive changes have been made, essentially all of the attractive features of the first edition [see DENO,N. C., J. CHEMEDUC.,42, 177 (1965)l have been maintained and. strengthened. The following important organization changes have been intro-
(Catinued on page A50g) Volume
48, Number 8, August 1971
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book reviews duced: (a) . . a useful summaw of material prrsentwl, eGpha~iring important prinviplei and rcavriuni i.i riven at the end of each chapter; ( h , mercicw nrp given at the endof e3ch chapter only, rather than being dlitribured thnrushout the ihnntcr text ns in the first edit&; (c) the ihehepter on Spectroscopy (nmr, ir, uv, ete.) is postponed until Chaptpter 7, after chapters discussing the shapes and other properties of alkanes, alkenes and alkynes, and bonding in simple and conjugated organic molecules. Among the key pedagogical strengths of the first edition were its clear style of presentation, its emphasis on direct data as a. means of generating intellectual models, and its pioneering attempt to soundly implant spectroscopic methods in the first organic course. These features are salient attractions of the second edition. In addition ta the stsndard material, expected in nearly all rwsilable modern organic chemistry texts, chapters on Enaymatic Processes and Metabolism, Heterocyclic Chemistry, Photochemistry, Polymers, and Cyclization Resctions offer a well selected group of topics not necessarily given satisfactory coverage in many other texts. In the reviewer's opinion, this text stands along with Morrison and Boyd's "Organic Chemistry" and Hendrickson, Cram, and Hammond's "Organic Chemistry" a? the outstanding texts for the first year Organic course. Roberts and Caseria's text stands close to Morrison and Boyd's text in terms of the more traditional "functional group" sppraach. The Roberts and Caserio text probably has a. stronger theoretical flavor than that of Morrison and Boyd, with the latter emphasizing comprehensiveness of reactions, more than Roberts and Caserio. Hendrickson, Cram, and Hsmmond's text is excellent in many respects, but many instructors may prefer to use it as a supplemental text rather than the main text, because of its strong organization structured about theory. Although the latter is an intellectually exciting and gratifying approach, it may he beyond the ability of many students, especislly those who take organic chemistry without s. strong proclivity for, or background in science. An instructor who anticipates adoption of an organic text will certainly want to inspect all three texts mentioned above before decidingon a find selection. Few criticisms can be leveled a t Roberts and Caserio's text, which must be considered as an important and timely contnhution to education in chemistry. A couple of minor points are: the presentation of ir and nmr spectra might be improved by (a) not breaking the ir spectra into two pieces (an idiosyncrasy of the particular machine employed hut which may confuse students into thinking it is important); (b) not hrwing intenseir pezks go off scale, since thisdistorts the inexperienced viewer'sperspective of "intense," "moderate," and "weak" hands; (c) although a very pretty discussion of spin-spin splitting is given in Chapter 7, the concept is
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Journal of Chemical Education
not used that much later on, especially relative to the concept of chemical shift (which the reviewer feels should be expanded substantially); ( d ) the nmr spectra should have a, uniform vertical scale, so that the inexperienced eye immediately associates relative peak position with chemical shifts. Finally little space is given to the new concepts of orbital symmetry control of certain organic reactions.
J. TWREO NICHOLA~ Columbia University New Yo&. N m York 10087
Guide to Organic Reactionr
Howard D. Weiss. Burgess Publishing Co., Minneapolis, Minn., 1969. vi 247 pp. Figs. and tables. 22.2 X 15 cm. $4.50.
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The purported primary objective of this hook is to provide undergraduate students with a dear, concise guide to the im~ortant general reactions o? organic chemistry. I t is intended as a supplement to campensate for the increased emphasis an theoretical and physical concepts in modern organic texts. To this end the author has succeeded admirably. However, one may question the universal need for such a supplement as a t least one of the most papular organic texts does, in this reviewer's opinion, an adequate job of summarizing the important preparations and reactions of the various classes of compounds. The book emphasizes the reactions used in the synthesis of a particular class of compounds rather than the rertctions which a class csn undergo, although these are summarized for all the important categories of compounds. The survey is quite complete, covering 48 classes of compounds with all the important, widely applicable syntheses included as well as many less common reactions. Reaction mechanisms are not discussed in any detail although reaction intermediates are shown in some instances. Each reaction is. written in general form followed by a brief (typically 50 words in length) discussion concerning its scope and synthetic usefulness; this particular feature is extremely heneficid and is probably the chief merit of the hook. Following the discussion, each general resotion is further illustrated by a. specific example. The only references cited are those to Organic Syntheses from which mmy of the examples have been taken. Although this is probably of little concern to the undergraduate student, it ma" he viewed as s. slieht disadvantaee if the hook i* utilized in .ilr.onlnnr~with the expec.t~tiot,sof the author n, n refrrenve and review guide to those who have completed their formal training in organic chemistry. I recommend this hook as a supplement to underereduate students eneaeed in a
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(Continued on page A604)
book reviews
seems to us that ~ a m m e t has t done a masterful job of illustrating end summarizing his chosen field, while also pointing the way toward further defor any one semester course, but on the velopmnttr and improve4 imdrrtnnding. other extreme, probsbly quite useful for Bent~,cthis book is highly pehonnl first year graduate students. well as an o~~tsrsndinccvan~~rle of svirnrific WAYNE C. DANEN exposition, it invites personal comments M. JORDAN Dnvrn Kansas State ~nivergity that may tell as much ahout the reviewers State University of Manhattan, 66608 as about the book. For example, we N m Yorlc at Potsdam, 13676 wonder if Hammett erred in presenting the thermodynamics of reactions in solution in the formal manner of Chapter 2 rather than in the relatively informal manner of Lewis and Randdl that Introduction lo Organic Reoclion Physical Organic Chemistry might have proved more useful to those Mechanisms who want or need a review of the pertinent LouisP. Hammett, ColumhiaUniversity, 0 t b TheodDr Benfey, Earlbam College. parts of thermodynamics before proNew York. McGrttw-Hill Book Co., McGraw-Hill Book Co., New York, ceeding with the rest of the book. NeverNew York, 1970. 420 pp. Figs. and 1970. 207 pp. Figs. and tahles. theless, Hanlmett has made a number of tables. 16 X 24 em. $13.95. 21.2 X 14 cm. 54.95. important points in this chapter that are sufficient to make it worth reading for Publication of the first edition of This is the fist hook of the McGraw-Hill everyone who is concerned with chemical Hammett's "Physical Organic Chemistry" Chemistry-Biology Interface Series inequilibria in solution. in 1940 was one of the most important stituted by CUEBS and ACn for the purChapters 4 and 5 can similarly be milestones in the gradual development of pose of improving teaching in areas of regarded as very important for all who physical organic chemistry as a recognized mutual concern to the disciplines involved. me concerned with chemical kinetics, and coherent scientific discipline. I t was ACI and CUEBS feel that "these books and should also be read by those who are fitting that this pioneering book should could, far the chemists, indicate the biointerested in the relationship between have been written by Hammett, who was logical significant reactions useful to experimental results and molecular models one of the early leaders in applying the illustrate chemical principles and, for the for chemical systems. In this connection principles of physical chemistry to organic biologist, summarize up-to-date informawe refer all scientists to Hammett's to report chemistry. Now it is a pleasure tion on molecular phenomena of sigremarks in the Introduction and elsethat Hammett's second edition is an nificance to a modern understanding of where on exact theory, approximate admirable summary and critique of large biological system." The intent of the theory, and empirical observations. portions of this field in which he has author of thiq book is to provide to heginHammett's clear present%tions of continued to he an active researcher. ning students a definition and illustration theories accompanied by illustrstive exBoth editions are largely concerned of the factors that influence reaction rates amples, generally in areas of considerable with reaction rates, equilibria, and mechand control the direction of chemical contemporary research interest, have led anisms'. Hammett intended his first change. us to the library to read papers he has edition to he encyclopedic in its chosen In Chapters 1, 2, and 4 dealing with, cited, to reach for slide rule and graph field, m d achieved that intention very respectively, delinition of a reaction mechpaper to test some calculation or correwell in just under 400 pages. Because anism, information obtainable from wnlation, m d also to plrtn some new exof the tremendous growth of physical centration studies and energy matters, periments. We are confident that other organic chemistry in the last 30 yearn, the the author frequently provides experireaders will be similarly stimulated. second edition is necessarily restricted mental data to illustrate the phenomena All physical organic chemists, most in its coverage, in spite of being slightly discussed. Because of this, these chapters organic chemist4, and many physical longer than the first edition. As Hammake especially interesting reading. The chemists should study this book. It is mett has explained in his Preface, this last two chapters deal with the carbonby no means an after-thought to connew edition is restricted to the area of carbon double bond end with other funcclude our review by pointing out that this reactions in solution, with radical rereectional groups. In these .chapters, hut also useful hook is also a. joy to read. tions excluded. Even with this restricsomewhat interspersed in earlier ones, is tion, he has found it necessary to be presented s. brief introduction to a variety L. G. HEPLERAND D. DOLMAN illustrative rather than encyclopedic. of reaction types snd how they may be University of Lethbridge The most concise way to describe the employed for the interconversion of funcLethbrdge, Alberta material covered in this book is to list tional groups. The discussion of the chapter titles as follows: (1)Introduction chemistry of these functional groups is by (2) The Thermodynctmics of Reactions in no means comprehensive hut does, howSolutions, (3) The Contribution from ever, present enough background so that Statistical Mechanics, (4) The Evaluation frequently illustration can he made of Introduction to Metal rComplex of Rate Data, (5) Transition-state Theory where these functional groups and their Chemistry (6) Some Displacement Reactions, (7) respective reactions occur in biological Salt Effects, (8) Effect of Solvent on systems. Only rarely is a mechanism not Minow Tsulsui, Texas A&M UniverReactivity, (9) The Quantitative Study fully explained. sity, College Station, Texas; Morris N. of Acids and Bases, (10) Rates of ReacContinuing a welcome trend in textbook Lay, Chemical and Solvent Distillers, tions Involving Acids and Bases, (11) writing, the author provides on occasion Astoria, New York; Akira Nakamura, Quantitative Relationshim Involvine references to the original source of the Osaka University, Toyonaka City, information, However, except for some Osaka, Japan, and Mitsw, Ichikawa, of the experimental data and a. few of the Japan Synthetic Ruhher Co., Ikuta, Changes. figures, this is provided only at the beginMochiieaka, Kawasaki City, Japan. As might have been predicted on the ning of sections or at the ends of chapters Plenum Press, New York, 1970. niii basis of Hammett's demonstrated exand does not serve to connect a reference 210 pp. Figs. and tables. 23.5 X 15.5 pertness in the fields of chemistry under with the mention of the information found cm. $14.50. consideration, his treatment is admirably therein. Also, it is a bit unfortunate that This book is the only available hook sound and remarkably up to date. It is more extensive use of references is not specifimlly covering metal rr-complex also wonderfully stimulating in much the made, for this would make the text more same way that a series of excellent semchemistry, a rather important branch of versatile for use in a course. inars is. A numher of historical and organometallio chemistry. Until other Problems are provided only sparingly persond comments throughout the hook books an this subject become available, in the book and are mainly used as a this book will have to senre as s. source of add considerable interest and give to this device for emphasis of materid immedisupplementary reading for the student of fine book an increased dimension. It ately prior. They are answered in detail. 3lore problem and without thcir antwers ndjnrrrrt would reuder rhc book more useful. If d l of the future texts of this series are of the same caliber, they will constitute an excellent set of texts for the teaching of hiologicsl chemistry.
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Journal of Chemical Education
organic or organometallic chemistry who wishes to enhance his understanding of certain principles peculiar to metal rcomplex chemistry. Other published books on organometallic chemistry either cover the field as a whole (eg., Coates, Green, and Wade), the whole area of transition-metal organometallio chemistry (e.g., King), or more specialised areas such as metal bensenoid complexes (Zeiss) or the iron group metallocenes (1Losenblum). This book is divided into seven chapters organized according to general topics in metal rr-complex chemistry. There are exercises st the end of each chapter. This feature makes the hook more useful for students. There is also a bibliography a t the end of each chapter, but this bihliography is limited to several general references. An introductory hook of this type would be much more useful if it provided a more extensive bibliography so that the reader with interest in exploring a topic in greater detail could be directed immediately to relevant journal articles. The fint chapter in this book discusses organometallic nomenclature but the names presented are not particularly systematic. Furthermore, Cotton's "hapto" system of nomenclsture is not mentioned. I feel that if nomenclature is specific&lly discussed, Cotton's system should also be discussed since it provides more definitive names for many of the complexes discussed. However, I feel that this chapter could easily have been eliminated and the space so relewd used for a better bibliography.
The second chapter discusses the p r e p arations of metd r-complexes. The classification of the preparative techniques is not particularly logical and the order irrational. Furthermore, eqn. 2-6 is wrong since Fischer and co-workers have shown that the benzene solvent rather than the benzene in the dibensenechromium is the source of the benzene ring in benzenetrioarbonylchromium. Other errors in this 5 chapter include depicting ( C . H S ) ~ Ma~ covalent rather than ionic (p. 23, eqn. 2 3 4 ) and the mysterious species "iron monocarbonyl" (p. 25). The third chapter discusses bonding in r-complexes. The clarity and conciseness of the ideas presented in this chapter leave much to be desired. The diagrams on pp. 30 and 31 are unnecessary since the points could be demonstrated more easily and concisely by simple electron counting. The diagrams on pp. 34 through 39 will unnecessarily ,confuse many readers. "Stibines" are erroneo~dycalled "stilhenes" on p. 44. The fourth chapter on spectroscopic and magnetic properties of metal r-complexes is probably the most useful chapter in the book. The szctions on infrared and nmr are generally well-written hot the section on mass spectroscopy is too brief m d sketchy to he of muoh use. The section on magnetochemistry does not mention the Fmaday method, an important technique for measuring the magnetic swceptibilities of organometallic compounds. The section on Mossbauer spectroscopy mentions "quadruple splitting" (p. 83) rather then "quadrupole splitting!'
Cyclohutadieneiron tricarbonyl is a poor example to use in the mass spectroscopy section since the reported fragmentation behavior is doubtful. The fifth chapter on structure and structure determination gives specific examples of key structures in metal rcomplex chemistry and the techniques, including X-ray ccrystallogrsphy, by which they were established. The examples are not presented in a logical order. Some figures are very poorly drawn (e.g., figures (5-I), (5-17), (.&18), and (5-19)). The nmr chemical shift scale used for the 16.8 cps peak of CsHsFe(CO)son p. 105 is not specified. The sixth chapter on reactions of metd rr-complexes provides a useful summary of much of their chemistry. Again this chapter contains some erroneous information notably eqn. 6-39 on p. 142, the discussion on the nmr of C,H,V(CO)8 on pp. 156 and 157, and the mention of the "cyclobutadiene-silver nitrite" complex on p. 162. The seventh and find chapter discusses catalysis involving metd r-complex intermediates. This chapter is a useful summary of an important area. of applications of metal r-complexes. In summary, I do not rate this book very high because of poor organization in some chapters and numerous errors as exemplified above. In addition, the number of typographical errors seems excessive particularly for a book costing 7 cents 5 (Catinued m page A606)
Volume 48, Number 8, August 1971
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book reviews page with not very much material on some pages. This book, therefore, is of value only because it ha8 no competitors. R. BRUCE KING University of Oeorgia Athens, 30801
New Volumes in Continuinr Series The following titles arc those of volums in conlinuing series. Many of Lhese serirs arc familior to rcaders who are best sarurd by prompt announcemmt of the appearance of the new titlcs. The policy of THIS JOUILXAI, will be lo publish full vmiews only of inaugural volumes in n m series. Progress in Analytical Chemislry. Volume 3, X-Ray and Electron Probe Analysis in Biomedical Research
Edited by K . M. Earle, Armed Forces Institute of Pathology, Washington, D. C., and A . J . Tousimis, Biocynamics Research Corp., Rockville, Md. Ple105 num Press, New Yark, 1969. ix pp. Figs. and tables. 16 X 23.5 cm. $12.50.
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Con~ibYors: D. F . Craston; William G. Banfield, A. J. Tousimis, J. C. Hagerty,
AS06
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Jourml o f Chemical Education
and Thomas R. Padden; Kenneth M. Earle; Louis Zeitz; A. J. Tousimis, Jon C. Hagerty, Thomas R. Padden, and Leonard Laster; A. J. Toosimis. Slruclure and Bonding.
Volume 7
Edited by P. Henmerich, Konstane, C . K. J w g a s a , Geneve, J. B . Neilands, Berkeley, Sir Ronald S. Nyholn, London, D . Reina, Bonn, and R. J . P. Williams, Oxford. Springer-Verlag, New York, 1970. 154 pp. Figs. and tables. 23.3 X 15.5 cm. $10.50. Contributors: D. W. Smith and R. J. P. Williams; R. D. Gillard and P. R. Mitchell; W. van Bronswyk; D. Reinen. Progress in Biophysics and Molecular Biology. Volume 19, Part 1
Edited by J . A. V . Butler, University of London, and D. Noble, Oxford University. Pergamon Press, Inc., New York, 1969. xxi 270 pp. Figs. and tables. 16 X 25.5 cm. $12.
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Contributors: A. C. T. North and D. C. Phillips; A. S. Spirin and M. S. Bretscher; A. Kepes; Claus Pelling. Progress in Biophysics and Molecular Biology. Volume 19, Part 2
Edited by J . A . V.Butler, University of London, and D. NobTe, Oxford University. Pergamon Press, Inc., New York, 1969. xix 194 pp. Figs. and tahles. 16 X 25.5 cm. $14.50.
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Contributors: M. R. Pollock: C. C. Congdon; 1%.H. Adrian; G. B. Arden; H. Passow. Acidity Functions
Colin If. Rochester, University of Nottingbam, England. Academic Press, Inc., New York, 1970. Volume 17 of "Organic Chemistry: A Series of Mono300 pp. Figs. and graph." x tables. 16 X 23.5 cm. $13.
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Annual Review of Physical Chemistry. Volume 21,1970
Edited by H. Eyring, Universityof Utah, C . J . Chrislasa, University of Utah, and H . S. Johnston, University of California, Berkeley. Annual Reviews 655 pp. Inc., California, 1970. ix 23 X 16 cm. $10.
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Contributws: G. J . Hoytink: J. K. Thomas; M. Krauss; J. J. M. Beenakker and F. R. McCourt; H. D. Rudolph; D. W. Turner; G. D. Halsey, Jr. and C. M. Greenlief; Benjamin Chu; P. B. Weisa; D. A. Leatbard and J. H. Purnell; S. H. Lin and H. Eyring; John Overend; A. D. Buckinghrtm and B. S. Utting; Adam Allerband and Elimbeth A. Trull; Leonard D. Spicer and B. S. Rabinovitch; R. H. Wood and P. J. Reilly; Marshall Fixmau and Walter H. Stockmayer; G. Wilse Robinson; J. W. Hastie, R. H. Hauge, and J. L. Margrave; J. C. Dalton and N. J. Turro; Piero Pino, Francesco Ciardelli, and Maurizio Zmdomeneghi.
