reviews Experimental
Organic Chemistry: A Miniscale Approach
Royston M. Roberts. John C. Gilbert, and Stephen F: Martin, Saunders College Publishing: New York, NY, 1994. xxvi + 801 pp. Figs. and tables. 21.2 x 26.2 cm. Although the title and preface do not so indicate, this text is a revised edition of Modern Experimental Organic Chemistry by R. M. Roberts, J. C. Gilbert, L. B. Rodewald, and A. S. Wingrove, the fourth edition of which was published in 1985. Much of the text and many of the figures are the same. The book is more attractive, with a slightly larger format and a second calm (blue) is used throughout to highlight and brighten up the pages. Comparison of the tables of contents reveals very few changes in the chapter titles and experiments included. The chapter Amino Acids and Peptides has been deleted. The predominant word in the title is "miniscale". Obviously, this is meant to suggest a compromise between classical and microscale, although in practice, it is closer to the former. The table gives a comparison of the miniscale text with the earlier fourth edition and with the macroscale version of Pavia et al. ( I ) . It can be seen that the quantities are considerably reduced from the fourth edition but are comparable to Pavia et al. and still much greater than the typical 50-200 mg used in micrascale. The text is organized into two sections, with techniques and
Each experiment is preceded by a "Safety Alert" and followed hy "Finishing Touches" (disposal,and exercises. The expenmenta are organized and thechapters ore entitled based on organic reactions and functional gmups. In contrast, the Pavia text is organized by applications (ex., flavors, detergents, dyes, drugs). A similar assortment of reactions is included in both texts. In summary, this text contains a goad assortment of experiments with a m ~ l ediscussion of theorv and teehniaues. One should not he mihed by the title-this i s a m a c r o s ~ a l e ~ ~ ~ r o a c h . It should be considered by those who prefer the classical organic laboratory. Literature Cited 1. Pavia, D.L.; Lampman, 0. M.; k z . 0.S. Inlmduetion to Ogonie Lobomtory W h nipuos. A ConlempororyAppmoeh, 3rd ed. Saunderr: Philadelphia. 1988.
Ronald D. McKelvey Universtiv of Wisconsin-La Crosse La Crosse. WI 54601
Second Edition John C. Stowell. Wiley: New York, NY, 1994. xv + 334 pp. Figs.
Intermediate Organic Chemistry, and tables. 16.3 x 24.3 cm. $49.95.
Comparison of Quantities Used in Experiments of Three Textbooks Experiment
Miniscale
4th Edition
Pavia et al.
Grignard
3.9 g of PhBr
18.8 g of PhBr 5.22 g of PhBr
Diels Alder
1.5 g of Maleic 6.0 g of Maleic 0.75 g of AnthranilicAcid Anhydride Anhydride
Acetanilide
3.7 g of Aniline 20.5 g of Aniline
NaBH4 Reduction
0.6 g of Fluorenone
2.0 g of Aniline
12.09 of AcPh 0.4 g of Camphor
spectroscopy a t the beginning followed by the experiments. There is a strong emphasis on spectroscopy, with a 90-page chapter in the first section. Infrared, proton NMR, and C-13 NMR spectra are given for most starting materials and products. Occasionally W spectra are included. A total of 401 spectra are listed in the table of contents. C-13 NMR's are generally tabulated data without multiplicities. Proton NMR's are generally a t 60 or 90 MHz, which may soon be obsolete. Unfortunately, many IR spectra are linear in microns.
As its title suggests, this hook (an update of a previous edition) is desimed for the student who has alreadv camdeted a stsndard two-semester introductory organic chemistry course but is not yet fully equipped to operate in the "real" specific case-oriented world of the oraetieine .. areanic .. chemist. Most of the oroblems resented at the end* uf each oithe 10 chapters been with tvplrally gsthwed rnw darn and requiw the student to solve a prohlrm from the beginnmg rather than from a half-hlshed retup. The topics selected in this compact 334-page book are a well-chosen broad spect r u m including nomenclature, searching t h e Literature, stereoehemistry, functional group transformation, carhon-carbon bond formation, planning multistep syntheses, mechanisms and predictions, electron delocalization, physical influences on reactions, and the internretation of NMR soectra. While the exnlanatiansof the various topics are brief, well organized, to the paint and clear, making ample use of appropriate examples and always assuming a working knowledge of the basic ideas, the main benefit will be eained throueh consultine the literature references cried and wmklng through the rptc~fieprablemr e v e n . In my upmion, these exerruses would be very helpful tu a student who wishes to undertake research with its necessity to search literature including the new computerized data bases, read current journals with understanding, design proper experiments, and analyze and explain the results.
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Reviewed in T h i s Issue Royston M. Roberts, John C. Gilbert, and Stephen F. Martin, Experimental Organic Chemistry: A Miniscale Approach J o h n C.Stowell, Intermediate Organic Chemistrty, Second Edition Henry Freiser, Concepts and Calculations in Analytical Chemistry: A Spreadsheet Approach Anthony S . Travis, The Rainbow Makers: The Origin of the Synthetic Dyestuffs Industry in Western Europe Textbook Announcements Monographs New Volumes in Continuing Series
Reviewer Ronald D.
McKelvey
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Peter R. Adams Daniel Y. Pharr
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George 6. Kauffman
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Volume 72
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Number 2
February 1995
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reviews Although this second edition retains the same 10 chapters ofthe first, new sections and examples with more detail have been added, the material reorganized and updated including stereochemical terminology and the inclusion of pulsed high-field NMR spectroscopy, and the number of exercise problems have about doubled. The author offers copies of an Instructor's Manual to teachers using this book. While there has been a great proliferation of chemistry texthooks afuneven quality in recent years, the number available that fill this particular niche so well or a t all is small indeed, and this book merits seeking out both as working text and for reference by all teachers and students who need organized knowledge a t this level.
Peter R. Adams Pennsylvania State University York Campus York. PA 17403
Concepts and Calculations in Analytical Chemistry: A Spreadsheet Approach Henry Freiser. CRC Press: Boca Raton, FL, 1992. 315 pp. Figs. and tables. 15.6 x 23.5 cm. $19.95 PB.
The text Concepts and Calculations in Analytical Chemistry: A Spreadsheet Approach exhibits a good deal of work by the author. We are fortunate in our department to have three analytical chemists involved in teaching undergraduates and in the use of computers. Each of us have used exercises similar to those outlined in this text. Our younger colleague has used the text as a reference for some of the exercises that were done in a two-hour romnnter lah that we have our m a ~ a r stake We have several elusMacintosh computers available to just the chemistry majors with Delta Graph as the graphics package. The problems with this text are the same ones we wouldencounter with any computer text. By the time the book comes out the software has changed. So t h a t t h e author may have made a mistake by relying totally on one piece of software. Therefore, I feel that mv comments as to the usefulness of this book should be made & to haw it would stand with any software. I encounter great difficulty here also because the graphing programs that I am familiar with, Excel, Cricket, Lotus 123, Mapley Sigma Plot, and Graftool were not designed to do what analytical chemists would like them to do. The programs like Graftool that allow one to write macros and the newer version of Excel 5.0, which includes a Visual Basic Application program included in it, might fill this need. However, the amount of programming required would get in the way of teaching elementary analytical chemistry concepts. Titration data is a ease in point. The spreadsheet will allow one to manipulate the data readily but the graphing function will not draw a smooth line unless a great number of data points are entered. Graphs when printed out do not have a grid that allows for anything approaching the two decimal point accuracy for the volume a t the equivalence point one would expect from an analytical experiment. In fact the computer work suggested requires more time with a large sacrifice in precision than it wauld take to make these graphs by hand on a good piece of graph paper. Similar prohlems are encountered with other software programs and examples in other chapters. Furthermore, the chapter an the statistical treatment afdata and quality control charts was not even covered. In the final analysis, computer and computer books should be measured by the same standard as any teaching tool. Does it increase productivity (take less time than manual methods) and, if not. will it increase the accuracv and oreeision of the analvsis. IJnfortunatelv the answer is "no" for man" of the eases in this mined what works best with the available software.
Daniel Y. Pharr Virginia Military Institute Lexington, VA 24450
The Rainbow Makers: The Origins of the Synthetic Dyestuffs Industry in Western Europe Anthony S. Travis. Lehigh University Press: Cranbury, NJ, 1993. Figs., tables, and photographs. 335 pp. 15.3 x 23.3 cm. $49.50. Frequently cited, hut rarely analyzed, the rise of the synthetic dyestuffs industry and the nature of its technology have remained poorly understood. This neglect has been corrected with the publication of a detailed historical reinterpretation of the 19th century's most remarkable seienee-based activity by Tony Travis, Deputy Director of the Sidney M. Edelstein Center for the History and Philosophy of Science, Technology and Medicine a t the Hebrew University of Jerusalem and an active participant far more than a quarter century in the textile and printing industries. Makine extensive use of the Edelstein Collection. world-renowned for its &erase of the histnrv,~of dveine as well as Brit,~ technolo& -,,~ ~"~ lih. E'rench, i h r m a n , and S w i s arrhlvri ;and impntianr hut lmlr. knaun sources, T r a w h c . w huw the invtnuun, udvenlsmg. ;and marketing of dyestuffs synthesized from coal t a r and the development of new routes to dyes previously obtained from natural sources revolutionized existing traditions in the preparation and use of dyes and created a new, broader tradition in which scientific knowledge became a powerful tool in the growth and control of technology. By exploring hitherto neglected aspects of social eontext, education, and the demand for new products Travis demons t r a t e s how t h e need for organized science to justify itself introduced science into industry and resulted in a mutual reinforcement of chemistry and dye-making and dye-using technalogies as the former solved problems posed by the latter. The 10-chapter volume is divided into four parts, each of which bears the title of an important synthetic dye. Part I, "Mauve" (35 pp), reconstructs in detail William Henry Perkin's serendipitous discovery (1856)of the first aniline dye and his subsequent manufacture and exploitation of his invention, a union of science and industry that became a model for the early synthetic dye industry in Great Britain and Europe. Part 11, "Magenta" (94 pp), describes how a multiplicity of interests (invention, seientific research, chemical engineering, and intellectual property rights) became im valved in the fledgling industry. Part 111, "Alizarin" (42 pp), demonstrates the profound transformation in the manner in whieh useful materials were created as a result of the changes in the theory of aromatic compounds. Part IV, "Indigo" (39 pp), records the consolidation of the German dye industry with the product development of phthalein and a m dyes and indigo after the mid1870's when the French industry declined and the British industry encountered serious difficulties. Patent arrangements helped the transfer of technology from Britain to Germany, leading to the formation of international cartels and modern chemical and pharmaceutical industries. Although Travis states that his "work is by no means a chemical treatise," it is replete with historical and modern structural formulas and equations, and it strikes a judicious halance between chemistry and history Lavishly illustrated with diagrams, phato~ p p h s sketches, . canuons. rharrs. Irtterc. and I ~ b m a t o r )nutei and fmturing an npprndtv 1 0 pp nates 51 pp . a h~hliogrnphy urth references ad recent a i 1YY2 110 up,, and rhree indrxw 19 pp), Travis' masterly study is essentiai&ading for organic ehemists, chemical engineers, historians of science and technology, and anvone interested in the orieins of the modem Western Eurooean chemical industry or of modem corporate organization in industrialized countries. ~~
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George B. Kauffman Calforn a Slate - n vers t y Fresno Fresno. CA93740
Textbook Announcements Transition Metal Chemistry: The Valence Shell in d-Block Chemistry Malcolm Gerloch and Edwin C. Constable. VCH: New York, NY, 1994. xi + 211 pp. Figs. and tables. 17.2 x 24.1 cm.
Volume 72 Number 2 February 1995
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