BOOK
REVIEWS
Experimental Organic Chemistry John Baldwin, University of Illinois, Urhana. McGraw-Hill Book Co., New 183 pp. Figs. and York; 1965. v tables. 17.5 X 25 cm. Paperbound. $6.50.
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This laboratory manual for undergraduale urganie chemistry represents a marked and deliberate departure from "the traditional organization [and contents, I may add] of elementary orgrtnlc laboratory texts-geared as these are to the preparation of representative compounds of certain functional group classepin favor of one based on techniques and types of reactions." This manual utilizes the newer meohanistic approaches to the presentation of organic theory. Even the titles of the experiments reflect its character. For example, Chapter 15 is titled Nucleophilie Addition to Unsaturated Carbon, rather than Isohorneol, Benzalacetaphenone, and B-Anilino-B-phenylpmiophenone, the compaunds prepared, or Reactions of Ketones, the functional group involved, or Reduction, Condensation, and Michael Addition of Ketones, the three tvnes of reactions illustrated.
takes into consideration the practicd limitations of time, equipment, siace, and funds. The experiments use semi-micro quantities of mrtterials, and most of the
experiments described within a. chapter can be oompleted within one threehour laboratory period, and nearly all in two periods. The experimental procedures are clearly described and the book has good illnstrrttions of even the simplest techniques. Each chapter contains a full discussion of the principles and mechsnismq involved and has well-conceived problems whioh clarify and exemplify these principles. Approximately onefifth of the hook is devoted to special methods such as the determination of reaction kinetics and equilibria by titration, distillrttian under reduced pressure, and reactions in en inert atmosphere. The important tools of I R and NMR spectroscopy, qualitative anslytical tests, and chromatographic techniques (vapor phase, thin layer, and ion-exchange) are introduced early. These techniques are used constantly in subsequent experiments so that the student is &en a full oieture The increasing important role of stereochemistry is shown by the dlotment of more than twa-fifths of the chapters to experiments which involve reactions, properties, or interconversions of strncturd and optical isomers. There am two appendices and an index. Appendix 1 gives the infrared and nuclear magnetic resonance spectra of 39 of the compaunds encountered in the manual, arranged in the order of increasing carbon
crmtlnl of llle indceuiw. 'llle spcmm are arranged 3, that both rhc I R and NIiIt spectra of each compound are printed on the same page. This arrangement gives the student opportunity to make useful comparisons of the values of these two tools. Appendix 2 lists the chemicals and equipment for each student locker-the estimated cost per locker is $86. This manual, presenting a sharp depsrture from the traditional manual, will find its best use probably in a course which departs fmm the traditional order in favor of the newer mechanistic approach. An undesirable feature was the use of the paperback cover. The informetion contained in this book will make it a desirable part of the permanent library of many students and teachers, and it is regrettable that its unusual shape and paperback cover may limit its utility. The book is well-mitten and is worthy addition to the literature of organic chemistry. All teachers who are using or planning to use the newer mechanistic approach and who are seeking 8. new and appropriate laboratory manual would do well to consider Professor Baldwin's book. Undergraduate teachers could use it with profit as a reference laboratory manual.
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P. MMLSS~E SAMUEL United Stales Naval Academy Annapolis, Maryland
Instrumental Melhods of Analysis Hobart H. Willonl, emeritus of the University of Michigan, Ann Arbor, Lynne L. Mem'tt, JT., Indiana University, Bloomington, and John A. Dean, University of Tennessee, Knoxville. 4th ed. D. Van Nwtrand Co., Inc., Princeton, New Jersey, 1965. xviii 784 pp. Figs. and tables. 16 X 23.5 cm. 510.75.
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-Reviewed
in this Issue
John Baldwin, Experimental Organic Chemistry Hobart H. Willard, Lynne L. Meritt, Jr., and John A . Dean, Instrumental Methods of Analysis D. W . Mathieson, editor, Interpretation of Organic Spectra. Nelson W . Hooey and Alhertine K~ohn,Qualitative Analysis William Horwitz, editorial chairman, Official Methods of Analysis of the Association of Official Agricultural Chemists Ya. G . Dorfman, Diamagnetism and the Chemical Bond David S. Schonland, Molecular Symmetry: An Introduction to Group Theory and Its Uses in Chemistry E. H.E . Pietsch and the Gmelin Institute, editors, Gmelins Handhuch der Anorganischen Chemie. 8. Adage, System Number 60, Kupfer. Teil B, Lieferung 3, Verbindungen KupfecLithium his Kupfer-Eisen. Reaktionen der Kupfer Ionen R. D. Peacock, The Chemistry of Technetium and Rhenium R. CoUon, The Chemistry of Rhenium and Technetium Walter Br&, Fundamentalls of Chemical Reaotion Engineering W . E. Dasent, Nonexistent Compounds: Compounds of Low Stability T. A . Turney, Oxidation Mechanisms Pierre Bipuard, FddBric Joliot-Curie: The Man and His Theories Nobel Lectures in Chemistry. Volume 2, 1922-1941
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Journal of Chemical Education
A rather careful examination of one segment of the latest edition of this wellknown book will illustrate how extensive have been the revisions in organization and content. Of Chapters 1, 2, 4, and 5 (116 pp.) of the third edition dealing with various aspects of ultraviolet and visible "colorimetry" and spectrophotometry, one (Turbidimetry and Nephelometry) has disappeared completely. A critical selection of the subject matter of the other three chapters has been made, and this material has been reorganized and blended with much that is new to form fourth edition Chapters 3 and 4, Ultraviolet and Visible Absorption Instrumentation and Methods (88 pp.). The result is a somewhat more informative and comprehensive treatment of fundamentals, although a few topics have been so abridged that some students, depending upon their interests and backgrounds, may wish to consult supplemental sources. Part of the reduction in the number of pagm now devoted to ultraviolet and visible ahsorption spectrwcopy has been brought about, not by sacrificing useful
text material, but. by the elimination of no fewer than 22 of the photographs of commercial instruments and a somewhat larger number of the line drawings that appeared in the previous edition. The photographs, in particular, were not only wasteful of space but are conceded by the authors to have been "relatively ~minformative." Nearly all of the remaining line drawings from the third edition have been revised, and replacing ouGof-date figures are a number of new schematic diagrams of which many show excellent perspeotive. Space has also been saved by the removal of detailed operating instructions for specific instruments, a feature of earlier editions that had been rather strongly defended by the authors. While the number of spectroscopy experiments in the corresponding chapters of the third and fourth editions remains unchanged, seven have been replaced by entirely new experiments while the remaining ten have undergone substantial revision. The26 exercises of oldchapters 1,2, 4, and 5 were nearly equally divided between discussion questions and numerical prohlenx, and had no answers. In new Chapters 3 and 4 there are 40 exercises of which 31 are new nnmerical prohlems with varying degrees of challenge; 15 of the latter are provided with answers. Finally, the earlier literature citations, many of which appeared as footnotes, have been thoroughly winnowed, updated with references through 1963, and placed a t the end of each chapter following a Bibliography. (An occasional reference to the 1964 literature appean in later chapters.) With the exeept,ion of six chapters, this, then is a reprmentative sample of the changes one finds throughout the entire bwk. Because of the continuing interest in infrared, fluoreseenre, and gas chromstographic studies and the increasing imoortanee of NMR. ESR. Raman and mass that It,? sl,ertnMylir;.. 11 I- tlut slllpr~~tng chapter?; drnling ntth thwc lopic< hxve nwdrrcone marked r~pnn.iicm. Their w tions on basic principles and instrumentation, especially, me now much more precise and a helpful new feature is the addition of numerical "Examples." Noteworthy, too, is the increased attention given to the application of the foregoing techniques in determining molecular structure. The authors' efforts have been no less product,ive in their expanded and improved treatmen& of X-ray, radiochemical and potentiometrir methods, and flame photometry. (Althongh one of their number is a recognized authority in the field, the reviewer questions whether the flsme photometric method merits having devoted to it the longest chapter in the book; this, especially, since the same author has brought forth an excellent complete work on this subject.) I n each of the updated chapters one of the most welcome changes is the inclusion of a large number of numerical problem. Completely new to the fourth edition are the thermogravimetric and differential thermal analysis topics in the chapter on Thermomalyticd Methods, a brief section on rttomio absorption in the Flame Photometry chapter, an entire chapter entitled Process Instruments and Automatic Analysis, and two chapters an Electronics.
The last named topic is one that is becoming increasingly popular and necessary in books in this field and the authors have given us a well-balanced coverage. However, in a treatment which is of necessity highly abbreviated, there would seem to he little justification for employing both of the opposing "positive current" and elec tron flow conventions. The novice, at least, is bound to be confused by their indiscrimmate use bath in text and on schematic diagram. Except far very minor changes, the chapters on Polarography, Amperometric Titration Methods, Polarimetry, Emission Spectroscopy and Conduotance Methods remain essentially as they appeared in the third edition, although in the last-named chapter, 20 new problems appear. I t would be hoped that in a future revision some consideration could be given to circular dichroism and optical rotatory dispersion which have become powerful structural techniques. These terms are now merely defined in the chapter on Polarimetry. I t is unfortunate, too, that the only alteration of sny consequence in the chapter on Refractometry and Interferometry has been the addition of a brief section on molar refraction based on a table of atomic refraction values that are long since obsolete. In correlations with molecular trtructure, bond refraction values are much more meaningful and rather extensive tabulations of these have been available in the literature far some time. Further, Batsanov's recent book, "Refractometry and Chemical Structure," seem to have rekindled some interest in this tool. For a work in which the rewriting has been so thorough, it would be surprising if there were not a number of errors. Very few of a typographical nature were observed, and the occasional incorrect page numbers in the Subject Index and faulty or omitted figure references in s. few problems are but minor annoyances. The new type style is especially pleasing to the eye. This reviewer can best summarize his impressions of the latest Willard, Merritt, and Dean by saying that it has now moved to the top of the list of those texts he recommends to his students of instrw mental analysis.
The failure to integrate these spectral techniq~tesis the major disappointment of this book. The overwhelming power of spectral analysis is best appreciated by the student when it is seen how these methods complement one anather. Despite this shortcoming thk hook should be rtn interesting mpplement for teachers of organic qualitative analysis.
JOSEPH WOLINSKY Pudue University Lafayette, Indiana
Qualitative Analysis
Nekm W. Hovel/ and Albertine Krohn, University of Toledo, Toledo, Ohio. Sernoll, Inc., Iowa City, Iowa, 1966. 132 pp. Tables. 22.5 X 28 cm. Paperbound. $3.75.
The authors have written a concise laboretory manual covering the qualitative analysis of 20 anions and 24 cations. The manual iis written for use in the second semester of freshman chemistry. The 20 anions are treated first in order to better correlate the lecture and labor* tory part of the course. The anions are not divided into groups but each one is treated individudy with six general reagents in order to familiarize the student with the properties of the ions before he analyzes an unknown. The reagents are: (1) 6N H&Oc (2) 36N I11S04,(3) KMnO* (4) KI, (5) AgNO* (6) BaCb. The reaetmns with the six general reagents are described in words and by an equation. Often an explanation of the reaction is given and the appropriate constants (ionization, solubility product, and instability) appear with the procedures. At the end of the section, a summary of all the reactions is given in tshular form. The final test for each anion is a. specific reaction which must be performed in the identification of the unknowns. At the end of the anion section, there are study questions as well as equations to complete and balance. The anion section is followed by 45 H. W. SAFFORD pages of theory. A very brief treatment University of Pittsburgh of equilibrium, complex ions, solubility Pittsburgh, Pennsylvania omduct. and redox eouilibria is wesented. 'Tables hf ionization Eonstents, instability constants, solubility products, and oxidsr tion potentials are included. The calculations of qualitative analysis are explained, fallowed by s. set of problems. The andysis of 24 common cations Inkrpmlation of Organic Spectra follows the section an theory. The cations are divided into the five u w d groups Edited by D. W. Mathieson, London --chloride, sulfide(scid), sulfide(hasic), University. Academic Press, Inc., New carbonate, snd soluble. Lead is included 179 pp. Figs. and York, 1965. ix in group one hut not in group two, so tables. 16 X 23.5 cm. $7. lead must be omitted from the general unknowns. In order to obtain better This book adds to the rapidly growing correlation between the class and laboralist devoted to spectral analysis of organic tory work, the groups are studied in compounds. The contributors assume reverse order (group five first). After an adequate knowledge of the principlq the preliminary exercises an the individual practice, and terminology of NMR, IR, cations are completed, directions and a snd mass spectroscopy and provide deflow sheet for the analysis of the gmup are tailed analyses of 12 NMR, 8 IR, and 10 provided. Study questions to check mass spectra. Six NMR and I R unthe understanding of the analysis are knowns are also presented.
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Volume 43, Number 9, September 1966
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507
