BOOK
REVIEWS
Burie Principles OF Organic Chemistry
John D. Roberts and Ma~jorieC. Caserw, both of California Institute of Technology, Pasadena. W. A. Benjamin, Ine., New York, 1964. xxv 1315 pp. Figs. and tables. 17.5 X 25.5 em. $13.50.
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The memorandum quoted below was sent to our chemistry faculty before we were asked to revievi "Basic Principles of Organic Chemistry" far THIS JOURNAL. There are several subjects in organic chemistry which we do not a t present cover in the introductory courses and which have become essential for the successful conduct of senior theses and the presentation of respectable seminars in Chem. 401 (senior seminar). These are: (1) NMR spectra, (2) infrared spectra, and (3) electronic (UV) spectra. The only introductory organic text covering these areas is Roberts and Caserio. This text thus merits our consideration and to stimulate discussion. some of the particular advantages of this text are listed below. 1. The print is large
6 0 that an old dog like myself can read it. 2. There are 128 raw spectre. presented. These occupy on an average about '/s. of B page each with a. few t&ng as much as
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page. They are beautifully portrayed. Probably half the total pages (1315) are taken urr with drawings and strueturd ffo~mulesso that the total amount of text is compsmhle to Morrison and Boyd (948 pages) or Cram and Hammond (846 pages). Study questions are good. I t is written in a very simple style and reasonably free of the one-upsmanship language that is strangling science. Proper emphasis is given to IUPAC and Chemical Abslracls nomenclature. The three texts we are currently wing [names d e leted], fault so badly in this matter that the student comes away using a style of nomenciature that is not acceptable to the editors of the J . Am. Chem. Sac., J . Org. C h a . , etc. The sweeping features of metabolic chemistry are presented. If these can be taught in general education physical science courses, they can be taught in introductory organic chemistry. To continue to leave out DNA, DPN, and messenger RNA is to teach organic chemistry further and further removed from the mainstream of current thought (and money). a
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in this Issue
John D. Roberts and Mariorie C. Case&, Basic Principles of Organic Chemistry 0.Theodor Benfey, From Vital Force to Structural Formulas
J. J . Lagowski, The Structure of Atoms A . A . Benedetti-Pichler, Identification of Materials via Physical Properties, Chemical Tests, and Microscopy Y . K. Syrkin and M . E. Dyatkina, Structure of lMolecules and the Chemical Bond Emil H. White, Chemical Background for the Biological Sciences Alezander I. Oparin, The Chemical Origin of Life Pe7-0200 Lowdin, editor, Molecular Orbitals in Chemistry, Physics, and Biology Robert Neher, Steroid Chromatography D a i s Taylor, Neutron Irradiation and Activation Analysis J . H. Wolfenden,Numerical Problems in Advanced Physical Chemistry J . Rose, Advanced Physico-Chemical Experiments G . Lepoube and M . J . Sienko, editors, Metal Ammonia. Solutions J . D. Lee, Concise Inorganic Chemistry Lloyd A . Munro, Chemistry in Engineering Cha~lesA . Reiehen, A History of Chemistry Robert Boyle, Experiments and ConsiderrttionsTouching Colours New Volumes in Continuing Series
8. Good ohspters on P, B, and Si chemistry are there if desired. 9. A similar statement can be made for the chapters on heteracyclica. 10. Polymers far once get a proper shake with profuse diagrams communicating the architectural problems in this area. 11. Natural products are emphasized and used as illustrations of the use of spectra. 12. Raw mass spectra, rotatory diipersion spectra, Raman spectra, and esr spectra are presented and interpreted. 13. The price is $13.50 and considering that it is 1315 pages, the price is reasonable. 14. The abundance of direct data (rather then generalizations) brings this text closer to experimental chemistry than usual. Thus the emphasis on the newer spectral methods is not a "flight to theory" but rather "back to the bench!'
The above memorandum was written to emphasize the merits of Roberts and Caserio. The one disadvantage is the physical size of the book. It is 55 mm thick and weighs about 2 kg. One new point and one reiteration can be added in retrospect. The new point is that optical isomerism gets properly presented. For example, the optical inactivity of meso-tartaric acid is explsjned in terms of statistical cancelling of the individual rotations of an assembly of rotational isomers (rather than the inadequate plane of symmetry explsnation). The reiteration concerns nomenclature. A current leading text introduces the substituted methane system for alkanes (trimethylethylmethane is exemplary) before the IUPAC system and the first study question contains ten such names. I t is no wonder that the student infers thia to be the preferred system despite what the professor says to the contrary. The fact is that every one of these ten names is not only unacceptable but it is difficult to imagine s, situation where they would be of any utility. In contrast, we find the emphasis in Roberts and Caseria entirely in accord with current journal requirements, strong commendation on this one point alone. NORMAN C. DENO Pennsyluania Stale Unwwsity University Park
From Vitol Force to Structurul Formulas
0. Theodor Benfey, Earlham College, Richmond, Indians. Classio Researches in Organic Chemistry. Houghton M a n Co., Boston, 1964. xi 115 pp. Figures. 15 X 23 cm.
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0 . T. Benfey conducts a guided tour through the original literature in this &at volume of a new paperback series, "Claasio Researches in Organic Chemistry." Intended for the student in elementary organic chemistry, the book not only rings Volume 42, Number
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this hell hut also provides good reading for any chemist. About one half of the book consists of well-chosen excerpts from the works of the founding fathers of organic chemistry, expertly woven by Benfey into a fascinating tale. Benfey sets the stage by a few pages on the state of the art just before Wbhler, with special note of the dualistic theory of Berzelins and its failure with organic compounds. He then discusses the Wahler-Liehig discovery of isomerism, Wdhler's synthesis of urea, and the impact of these two events on the chemical world: the vital force doctrine had received its first challenge and organic chemistry as physical science was under way. Hewing to objectivity rather than either legendbreaking or legend-making, Benfey writes, "there is no doubt that the urea synthesis provided a powerful impetus to chemists trying to find order in the field of organic chemistry.. . . The synthesis of urea did not of course immediately destroy the dichotomy between the realms of organic and inorganic chemistry. . . . However, even the discoverv of a horderline case was important, f o r . . [a] marginal region can be explored and many chemists were fascinated by the prospect." (Pp. 23-25.) The first major advance after the urea breaktbrough was the radical theory, initiated by Liehig's and WBhler's work on henzoyl. Benfey captures the essence of this rather complicated piece of detective work in a remarkably clear manner. The case of the smoking Tuileries candles then leads to Dumas and the substitution theory, squarely in opposition to the dualistic theory and setting off the furious and sometimes hitter debate that occupied organic chemistry far two or three decades. The reader is guided through the tangled controversies and oantrihutions of Laurent, Gerhardt, Dumas, Williamson, and others and gains an unusually clear picture of substitution, radical, and type theories. The work of Frankland, Kekul6, and Couper then comes as an intellectual climax to the story. Benfey's excerpts from and comments an Couper are particularly revealing of the background of genius. Editor Harold Hart, in his introduction to this hook, says that "scientific discovery is a thrilling and exciting process, and a zest for it should he imparted to the heginning student." These words are wellfitted to the hook, which should be enjoyable and worth-while reading for both teachers and students.
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lected excerpts from the original literature, tied together and explsjned by s knowledgeable writer. As a result, the student gains a picture of science as an active pursuit of bowledge, as opposed to the too-familiar picture of science as a passive body of knowledge. In this volume, J. 3. Lagowski deals with atomic theory from Thomson to Bohr. Liberal use of original passages and diagrams from the works of Thomson, Rbntgen, Becquerel, the Curies, Rutherford, Soddy, Moseley, and others provides a vivid account of the how and why of the discoveries of the electron, radioactivity, isotopes, and the nuclear atom. The final major topic is the Bohr atom, which is handled well hut without the extensive quotes and excerpts which mark the rest of the hook. Students who are not acquainted with elementary physics will perhaps not follow same of the mathematics, hut this should not interfere with their grasp of the mein trend of thought. All in all, the book is not only understandable hut also an invitation to further studv. The teacher who recommends this hook to his students should perhaps clarify one point. Lagowski implies that classical quantum theory was completely successful m d then writes that wave-particle complementarity is a philosophical problem, thst "the nature of science is such that new ideas [sic] continuously alter the results of previous theories," and Iinally that "the results of these [wave-mechanical] calculations agree in general with those of the more simple Bohr concept." The impression a beginning student is likely to get is that the Bobr theory is an entirely valid one and that physicists later arhitrarily chose to make things unnecessarily complicated. The genius of Bohr and the hddness and worth of his "atom" would he better served by a frank account of the limitations of the theory. Nevertheless, the hook should he a good adventure in thinking for freshmen. I t is not merely a history book hut rather a unique opportunity to read some of the aetud archives of science a t a level 80cessihle to the non-expert and even to the beginning student.
IRWIN COHEN Youngsfown University Youngsfown,Ohio
Identification of Materials via Physical Properties. Chemical Tests, and Micror-
kouncstown, O ~ W
The Structure of Atoms
J. J. Lagmuski, University of Texas, Austin. Classic Researches in General Chemistry. Houghton Mifflin Co., 120 pp. 15 X Boston, 1964. vii 23 cm. $1.95.
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This paperback is one of the fint under the series title, "Classic Researches in General Chemistry." The objective of the series, successfully fulfilled here, is to provide beginning students with se-
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Journal of Chemical Education
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A. A. Benedetti-Pichler, Queens College of the University of the City of New York. Acsnlemic Press, Inc., New 492 pp. Figs. and York, 1964. xi tables. 17 X 25 em. $18.
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A chemist is frequently called upon to answer the questions, "What is it?" and "What is its chemical compcmition?" Samples brought to him may vary from Imee -~ rooks to ~oeeks of imourities in an ~~~-~ otherwise pure substance. 'The &blem of properly identifying an unknown suhstance is indeed a difficult task and the chemist will find this book very helpful. The author points out that '%he hook has
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been written for the practicing chemist whose occasional task may be qualitative I t emphasizes the identifianalysis.. cation of materials-inorganic, organic, biological, common, rare. .as they actually occur in nature and industry.. ..'I The hook emphasizes techniques and methndology rather than theory. It is divided into two parts. Part I (about 200 pages) is concerned with the technique of observation and manipulation. The first section gives an excellent discussion on the use of the microscope with clear and detailed directions. Part I diieusses such various teohniques as work on the gram, centigram, milligrrtm, submilligram, and microgram scales. The section on the submilligram scale includes directions for spot tests and microscope slide tests. In all sections, specific experiments and practice exercises with detailed directions are given. This is especially valushle since the investigator is able to carry out the experiment with a known suhstance to develop his technique and to verify the accuracy of the
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Part I1 (about 250 pages) discusses systematic analysis. The following topics are covered: sampling, preliminary inspection, non-destructive testing, classification tests, and a lengthy section on eanfi~matory tests for various cations. Separation methods are then discussed followed by detailed flow diagrams for the separation and identification of the cations including the rarer elements such as beryllium, tungsten, uranium, etc. Most of these follow the classical scheme of 'qualitative sndysis using hydrogen sulfide. This is followed by a section covering a systematic procedure for the anions. Part I1 concludes with a section in which Dr. Benedetti-Pichler states, "the most important part of the analysis is the final conclusion." His suggestions should be verv, heloful. Tlrc .\ppcndir (rlwll 20 paycr) included d~rcct~ons for prepanti): mt sdutions and unknowns. (Directions for preparing various reagents are usually included with each specific procedure). Tables of crystal forms, colors, and melting points of inorganic compounds are given. The final section consists of approximately 1200 references oonveniently arranged in various categories. Most hooks in the field of qualitative analysis are highly specialized, i.e., inorganic, arganio, microscopy, instrumentd, etc. In order to identifv a substance of unknown comuosition. ihe snalvst mav find it uecess& to cdnsult seve;al references before he can find a. workable method. Dr. Benedetti-Piehler has masterfully presented d l of this in a single volume. The bookis well organized, clearly written, and reflects the author's many yeam of experience in the field. It is recommended for the libraries of all chemists concerned with quditative analysis and should serve also as a. useful textbook for a senior-level course in identification analysis.
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R l c ~ n n oB. HAHN Wayne Slate University Detroit, Michigan
(Continued a page ABO)
