Experhnental Elementary Organlc Chernlstry
book reviews
James A. Moore, University of Delaware. W. B. Saunders Company, 1974. Figs. and tables. vi 243 pp. 16 X 24.5 cm. $5.95.
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Chernlstry: A Science lor Today Spencer L. Seager and H. Stephen Stoker, Weher State College. Scott, Foresman & Co., Glenview, Illinois, 1973. x 469 pp. Figs. and tables. 24 X 20 cm. $10.95.
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With the advent of respectahilily for the reaching of science to non-srience rnsjorr has come a steady stream of texts for the purpose. In t h e case of chemistry texts the orientation toward the non-science major is sometimes little more than a catchy "relevant" title affixed to a traditional general chemistry text. If the text has in fact been oriented toward non-science majors, then i t is certain t o invoke the wrath of many teachers; for although all teachers of ehemistry may agree on the need t o teach chemistry t o the masses, there is little agreement on what should he taught or on how it should be taught. "Chemistry: A Science for Todav" elearlv falls in the latter c a b gory, and the authors state that this "textbouk represents our rontrihution to the contruversy" w e r "eowses designed for the general education of today's college stu. dents." Some of the features of this hook which are intended t o help the nonmajor gain an understanding of chemistry are the following. First, the material in the descriptive section (approximately two-thirds of t h e hook) is relevant in the good sense of that word. Chapter 14, "Some Interesting and Useful Nonmetals," for example, covers only phosphorus, carbon, and silicon; and Chapter 15 on metals covers only iron, coinage metals, and aluminum. The elements were selected in each instance because they or their compoueds are familiar t o the layman. Chapter 13, "Some Important Industrial Chemicals," covers the five chemicals manufactured in largest amounts in the U.S. Other descriptive topics indude nuclear processes, electroehemistry, organic chemistry (4 chapters), biochemistry ( 3 chapters), medicinal chemistry, and pollution (2 chapters). ~
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Second, "in a few instances, where the change makes very little difference in the ideas being taught," the authors "have used terms or concepts that are a little less than rigorously correct hut are more familiar t o the student or more easily understood." The use of weight rather than moss is cited in the preface; I was unable t o find another example. Only one definition of entropy, namely, the extent of randomness, is given. I am disappointed that the term mole is used. Although this approach will be condemned by many, there are also many of us who feel that scientific jargon is one of the harriers to a n understanding of science by t h e nonscientist and that a text of this type should avoid unnecessary jargon. A third feature is the clarity with whieh the text is written, always important but especially important in texts for nonscience students. Other features are the care and detail in presentation of explanations. best shown in the emlanations of problem sohing in Chapter 9. "Chemical Calrulationr:" and the Suggestions for Further Heading provided fur most chaptersreferences t o interesting articles in ChemN o , S c t ~ n r z Scienriltr A m e n ~ o n ,and .lourno1 o i C h e m w 1 Edurorion The formar of the hmk is attractive and the production has been done with care: only four minor errors were found in an examination of more than half of the chapters. There are numerous well-drawn diagrams. The only criticism ia a very minor one. Each chapter is preceded by a black and white photograph without caption (the titles are hidden on the back of the title page). The photos look like they belong in a "What is it?" phota quiz; in my opinion they add nothing scientific or aesthetic. If you teach general chemistry t o nonscience majors, I highly recommend this textbook for your consideration. ~~
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Willlam R. Roderick Rooseven Univem#y Chicapo, Himis
Reviewed in this lssu
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Spencer L. Seoger and H. Stephen Stoker, Chemistry: A Science for Today James A. Moore, Experimental Elementary Organic Chemistry Thomas L. Jacobs, William E. Truce, and G. Ross Robertson, Laboratory Practice of Organic Chemistry, Fifth Edition J. H. van der Moos, Interpretation of Infrared Spectra, An Audi-Visual Programme Gilles Klopman, editor, Chemical Reactivity and Reaction Paths R. D. Leuine and R. B. Bernstein, Molecular Reaction Dynamics Almon G.Turner, Methods in Molecular Orbital Theory H. Moenke, and L. Moenke-Blankenburg, Laser Micro-Spectrochemica1 Analysis George S. Ernmerson, Engineering Education: A Soeial History New Volumes in Continuing Series
.. .A385 . ..A385
...A386 ...A386
...A386 . ..A387 . ..A388
...A388 ...A388 . ..A389
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There is no such animal as the lahoratory texthook in organic chemistry. This is particularly true of a laboratory manual designed "primarily with the needs and interests of health science majors in mind," for no group of students presents a greater challenge in terms of needs, attitudes, emphasis, and degree of sophistication. How well the author has succeeded will depend upon the nature of the one-semester course the teat must serve. (The teat is designed t o supplement Moore's "Elementary Organic Chemistry.") There is something in this text for everyone, not enough for some, and too much for others. The author states firmly that he believes (1) experiments should require a minimum of equipment and chemicals and (2) the students to whom this text is addressed need clearly detailed instructions for suecessful completion and understanding of the experiments they perform. Both of these objectives have been met. For examole. the column chromatoeraohv exoeri.. . k t 1Ch. 6 ) utilize* an eyedropper as rhe culumn nnd reqt~iresnu suctiun. a common hugnhoo in large lah sections if aspirators are used. Other experiments, such as the reactivity of alkyl halides (Ch. 10) and the chemistry of alcohols (Ch. 11) require testtube quantities of materials. The tlc experiment (Ch. 7) uses inexpensive commercially available analgekie drugs and is designed t o maximize the use of economical commercial tlc sheets. Discussions of the principles involved in each experiment are good, though brief, and experimental procedures are outlined clearly and in simple terms. In a few places, however, the discussion of principles is weak. The treatment of theoretical and percentage yields (Ch. 1) is superficial and unclear. Many students have considerable trouble with these concepts. More emphasis should he placed upon melting point ranges (Ch. 2) and the fact that only impurities soluhle in the melt have an effect upon the melting point of a solid. In Chapter 12 the mechanism of aromatic nitration is begun in detail and then truncated for no apparent reason. All of the major laboratory techniques necessary in organic chemistry, with the exception of gas and paper chromstography, are illustrated with good experiments and reinforced later. Most of the maior chemical reactions encountered in a onerernester organic chemimy course are also illurtrated with eaperimentn, although e m densation reactions, esterification, and reactions of alkenes and alkynes are, for the greater part, omitted. Interesting, thaught-provoking questions and tear-out laboratory report sheets, which lead the student by the hand in taking data, appear a t the end of each chapter. The instructor's manual whieh accompanies the text contains useful information such as materials and amounts of chemicals needed, prohletns that may he encountered, and answers to the questions a t the
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Volume 52. Number 8, August 1975 / A385
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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A386 / Journal of ChemicalEducation
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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