them both safer and less expensive than macroscale laboratories; and they greatly reduce the problems of organic waste disposal. They also promote careful lahoratory technique. On the other hand, they do not expose studentsto methods such as classical vacuum distillation or to the use of equipment such as separatory funnels. Furthermare, many instructors feel that an organic lahoratory that is all microscale causes students to miss the importance of thermochemistry in organic reactions. Others are reluctant to abandon their traditional lahoratory procedures, because they have a heavy investment in standard-taper macmscale glassware. They might like to try a few microscale experiments, hut they are not ready to convert to a fully microscale organic laboratory. This hook will allow the addition of microscale syntheses into the organic lahoratory on a gradual basis. There are many procedures that require little or no new equipment. Macroscab ondMieroscale Organic Experiments presents lahoratory exercises geared to both scales, so the instructor may choose as many or as few of each typeas seemappropriate. The hook is a combination of Fieser and Williamson's Organic Experiments and Williamson's Microseale Organic Experiments. There are 74 chapters, most of them dealingwith organicsyntheses. In most cases the same synthesis is described using both macr o andmicro techniques. Logo printedin the margin next to each procedure clearly indicate whether the exercises are macroscale (half-filled round-bottomed flask) or microscale (slightly filled test tube). Important notes regarding each Laboratory exercise are stated briefly in the margins, where they almost surely will be read. When the notes are concerned with chemical toxicity or the safe handling of potentially dangerous materials, they are printed in red; and when a substance is especially hazardous, the note begins with the ward Caution! Certain chapters should be mentioned specifically. Chapter 1is an introduction to the organic laboratory and its equipment; it even includes such things as how to clean glassware and how to keep a lahoratory notebook, Chapter 2 diseuases laboratory safety and waste disposal. The next eight chapters deal with important organic laboratory procedures: crystallization, m.p. and b.p. measurements, distillation, steam distillation, vacuum distillation, sublimation, extraction, and chromatography. Chapter 16 is an exercise in the use of liquid chromatography; Chapters 19-21 deal with theuse of spectroscopy-IR, NMR, andUV; Chapter 69 is a practical exercise in blowing, bending, and simple mending of glass; Chapter 70 is a brief course in qualitative organic analysis, complete with tables of melting or boiling points for more than a dozen classes of organic compounds; and Chapter 74 provides information on using the literature. Prelah exercises are suggested a t the heginning of most chapters, and questions are given at the end. One of the unique features of this book is that each experiment concludes with a short paragraph on "Cleaning Up". Instructive diagrams of apparatus and how to use it are numerous and excellent. In addition, there is a list of general safety rules just inside the front cover, along with First Aid instructions in case of fues, spills, or other kinds of accidents. Inside the hack
cover is a handy centimeter ruler along with information about the concentrations of common acids, bases, and buffer solutions, as well as tables of atomic weights and multiple atomic weights (carbon up to Csa, hydrogen up to Hss, oxygen up to Ole, etc.). The author seems to have thought of everything that might make this versatile book as helpful and as easy to use as possible. Perhaps he might even be faulted for having included too much. The hook is a veritable encyclopedia of organic laboratory experiments. Yet the directions given are so concise and carefully written that even with the easilv readable h e used. the hook runs on~yahout700 pa& I think that every organic chemistry instnrctor, along with many others, will want a copy of this hook.
Doris Kolb Bradley Unlvershy Pmia, IL 61625
Chemlsche Studlen, I: A. COnslltutlons-Formein der organlschen Chemle In geographischer Darstellung; B. Das Marlotte'sche Gesetz J. Loschmiin. Carl Gerold's Sohn: Vlenna, 1861; reprinted by Aldrich Chemical Co., P. 0. Box 2060, Milwaukee. WI 53233, 1989. 54 pp. 7 plates. 13 X 20 cm.
$12.00. J. Loschmldt's Konstnutlom-Formeln der organlschen Chemle In graphlscher Darstellung Richard Ansch&. Ostwald's Klassiker der exakten . - Wissenschaflen Nr. 190. Wilhelm Engelmann: Leipzig, 1913; reprinted by Aldrich Chemical Co.. P. 0.Box 2060. Milwaukee. WI 53233. 1989. 154pp. 13.2 X 20.1 cm. $12.00. ~
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The shy and self-effacing Johann Joseph. h c h m i d t (1821-1895) (see Kohn, M. J. Chem. Educ. 1945,22,381) is best known to chemists and physicists for his 1865calculation of the number of molecules in 1cc of a -eas .(Loschmidt's number) and for the first accurate estimations of the size of m "-a mole~-~rules. However, of equal or even greater imponance to chemists was his first scientific work, Chernische Studien, I (apparently a part I1 was planned but never written), published at his own expense when he was 40 years old. In the words of William J. Wiswesser, this "first picture hook of molecules" was "the masterniece of the centin mganic chemistry" (CWIK 1,wt News January 19R9.1;AldrmhtrnreoArto 1989.22 (1),17). Aleksandr ~ i k l d l o v i c hButlemv, who f m t proposed the term "chemical structure," declared that "The future task of chemists is to determine the arrangement of atoms in molecules," and Loschmidt's contrihution to solving this problem has been sadly neglected. His slim pamphlet of 1861 vividly demonstrates how far ahead of his contemporaries he really was; it contains a veritable cornucopia of chemical "firsts," among which may he listed: (1) the first graphic representation of molecules with atomic domains rather than abstract bond lines (368 structures in seven fold-out nlates):.. (2) . . the first cvclic structure for hennene and aromatic eompunda (121 stmcturea) four years before Kekule's celebrated hexagonalstructureof 1866 (Lowhmidt rec~~
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Volume 66
ognized toluene as methylbenzene and therefore explained the isomerism of cresol withbenzyl alcohol): (3) the first double and triple bond designations (ethylene and acetylene a n d derivatives); (4) t h e first representation of vinyl and d y l groups; (5) the fmt realistic depictions of atomic sizes and hond distances ( C 4 < CkC < C--C): (6) the first representation of cyclopropane; (7) the first diagrams with correct C = 12, N = 14, 0 = 16 formulas (a year after the Karlsmhe Conference); (8) the first textbook use of functional group symbols (e.g., Hd for hvdroxide. Id for imido. Ad for ami~~
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( ~ & & i d t used theterm Pollenr; the term V a l ~ n rwas introduced by Hennann Wichelhaus in 1868); (10) the first pro-1 of tetravalent and hexavalent sulfur; (11) the first recognition that in alcohols containing several hydroxyl groups each carbon atam can hond to no more than one OH group; (12) the first recognition that ozone consists of three oxygen atoms; and (13) the first line-formula natations (to reduce printing costs). Losehmidt devoted 47 pages to his essay on structures; the remaining sia-page essay, "Spannkraft der Gase," deals with the physics and kineties of gases. Like Avogadro's hypothesis, published in 1811 in a journal read primarily by physicists (Joumol de Physique 1811.73,58) and negleded by chemists until resurrected hy Stanislao Cannizzaro a t the Karlsruhe Conference in 1860, Loaehmidt's privately printed opus languished in obscurity for more than half a century. In 1913 Richard Ansehiitz, KekulC's successor a t Bonn (Kauffman, G. B. J. Chem. Educ. 1982.59, 627, 745), republished it as a volume in "Ostwald's Klassiker der exakten Wissenschaften" series. He made some minor corrections in the structures, incorporated into the text the structures originally depicted an seven original, awkward, easily torn, fold-out plates, and added an autographed portrait and an ll-page biography of Loschmidt and 46 pages of 208 annotations to Loschmidt's text. I t was Anschiitz's reprint that Bill Wiswesser discovered in the Lehigh University Library in the early 1950's and that inspired him to develop WLN (Wiswesser Line Notation) (Wiswesser, W. J. A Line-Formula Chemical Notation; Thomas Y. Crowell: New York, 1954). Both Loschmidt's original book and Anschutz's reprint have until now been extremely difficult to obtain. Now, thanks to Alfred Bader, Chairman of the Aldrich Chemical Company and Bill Wiswesser, each avid aficionados of the history of chemistry, both these rare historical classics are available at an extremely attractive price. Of the two, Anschritz's reprint is somewhat clearer and will probably he of greater utility to chemical educators and practicing organic chemists. However, the historian of chemistry and the chemist interested in the historical development of chemistry will also wish to make the original pamphlet part of his or her awn personal library. As an extra added attraction, for those purchasing either book Wiswesser has prepared an IBM PC floppy disk master with six indexes-41) authors (Anschiitz's as well as Loschmidt's citations), (2) German subjects, (3) German names, (4) German chemical index with Anschiitz's modem equivalents, (5) English names, and (6) WLN structures (to all cited (Continued on page A282)
Number 11 November 1989
A281
item in the text, figures, and annotations). Thus, modem technology comes to the aid of the muse Clio. The disk is available on request from Dr. William J. Wiswesser, 3124 Stoudts Ferry Road, R e a d i , PA 19605 George B. Kauffman Caiitrmie State VniueRihl. Fresno Fresno. CA 93740
A282
Journal of Chemical Education
