A Short Course In Organlc Chemldry Edward E. Burgoyne, McGraw-Hill, New York, 1979. vii 527 pp. Figs. & tables. 24.5 X 19.5 em.
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study Gulde with Solutions to Accompany Burgoyne: A Shod Course In Organlc Chemldry
N.Sue Horner. v + 197 pp. Fig%.&tables. 23 X 19 em. $6.95.
The World ol Organic Chemldry: A Laboratory Approach David C. Eoton, McGraw-Hill, New York, 1979. vii 355 pp. Figs. & tables. 23.5 X 19 cm.
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A title such as "A Short Cmrse in OrgnnicChemistry"seems to he-at least,tomort organic chemists-a promise uithr impwssi. ble. One often suspects that one-term courses are designed to give the nursing, biology, agriculture, and home economics students who take them the right toclaim they have "had" organic chemistry without subjecting them to the intellectual exercise that is crucial to understanding the subject; hence authors of texts for "short" organic courses are sometimes accused of false advertising. Edward Burgoyne has succeeded rather well in making good the promise and designing an or. ganic course that get9 the student helow the surface of the suhiect d e s ~ ~its t ebrevit~.In fact. the entire three-book ~ a c k a e of e which thiaiext is~ the mime . ~ . ~ . ~~~ . ~ memb;r is a k n e a basis far teaching a sound and stimulating oneterm organic course as one is likely to find. Professor Burgoyne has pared away skillfully leaving those topics that are necessary and interesting only to chemistry majors. He focuses, in the chapters on functional group ~~~~
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families, on chemical behavior rather than roles in synthetic strategies. He omitp lengthy discussions of such subjects as elimination versus substitution, NMR, contributions to rihg strain, electrocyclic reactions, and carhonium ion rearrangements. Yet he avoids the "organic-as-memorizationtrap" by including the theoretical and mechanistic essentials that allow the chemistry to make sense to the student. There is treatment of bonding and molecular geometry, energy profiles, resonance, and the key mechanisms of organic reactions-Sd, S N ~E, l , E2, electrophilic addition, aromatic substitution. There is an appropriate emphasis throughout on biochemical, medicinal, and otherwise relevant compounds. Ample use is made of equations and clear, attractive illustrations. Each chapter includes strategically-placed study problems, a complete summary, and a list of key terms. The accompanying study euide bv Sue Barnes orovides for each chaon~ ~, tcr in the text ~upplementaryreadings, answers toall pruhlems, and a self-tcating %PCtion. There are no glaring weaknesses to report. From the discussion,the student is apt to get the erroneous impression that hybridization involves a kind of excited state; London forces are not so generally overshadowed, as the baok implies, by dipole-dipoleforces; free energy change is not defined precisely; Cahn-Ingold-Prelag problems based on Fischer structures are nearly impossible for the beginning student. The self-testing sections of the study guide are of the fill-inthe-hlank variety. The authors of both the text and laboratory manual split an oeeasional infinitive. But these are largely noncritical deficiencies. "The World of Organic Chemistry," the laboratory manual in this package is not only a superb collection of experiments for a non-majors course, but also it is a treasure ~
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trove of fa& that the organic chemistry instructor will find valuable for illustrating lectures-a list of Nobel prize winners in Chemistry and Physics, compositions of various commercial analgesics, structures of all sorts of pberemones, chemosterilants, artificial sweeteners, esters responsible for common flavors, and antibiotics, for example. The author claims that the book represents an innovative approach to teaching organic chemistry in the laboratory. While it is true that a majority of the experiments make use of compounds that are likely to pique the interest of the non-chemistry major, the greatest novelty of the manual lies in its extensive use of well-researched background information. The result should be an experience that not only makes the stark structures on the Dazes of text and manual come alive fur thestudent, hut alw helps integrate chemistry into the overall educational process ~~~~~
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Gerald W. Gibson College of Charleston Charleston. SC 29401
Catalytic Hydrogenallon In Organlc Syntheses
Paul N. Rylander, Engelhard Minerals & Chemicals Corp., Menlo Park, New Jersey. Academic Press, New York, 1979.. Figs. & tables. 23.5 X 15.5 cm. x 325 pp. $34.M1.
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Since the discovery of catalytic hydrogenation by Sabatier and Senderens in 1897 there has been no single comprehensive monograph an this sole topic until 1965. In that year, two books, R. L. Augustine's "Catalytic Hydrogenation," and F. Zymalkowski's "Katalytische Hydrierungen," were published almost simultaneously in the United States and in Germany, respectively. Since then two more authors, M. Freifelder and P. N. Rylander, essentially monopolized (Continued an page A1 74)
Reviewed in This Issue Reviewer Gerald W. Gibson
A173
Paul N. Rylonder, Catalytic Hydrogenation in Organic Synthesis
Milos Hudlicky
A173
Earlene Brown Cunninghorn, Biochemistry: Mechanisms of Metabolism
Joan Lusk
A174
Marwin W. Kemp, Physical Chemistry: A Step-By-Step Approach
Jeff Davis
A174
Curtis T. Sears, Jr., and Conrad L. Stonitski, AspRelated Sciences
Christina A. Bailey
A176
Eduord E. Burgoyne, A Short Course in Organic Chemistry, N. Sue Barnes, Study Guide with Solutions to Accompany Burgoyne: A Short Course in Organic Chemistry, Douid C. Eaton, The World of Organic Chemistry: A Laboratory Approach
of Chemistry for Health-
Volume 57. Number 5, May 1980 / A173
book reviews
the field of catalytic hydrogenation with the books "Practical Catalytic Hydrogenation" (1971) and "Catalytic Hydrogenation over Platinum Metals" (1967). Most recently, both authors revised, updated, and renamed their respective books "Catalytic Hydrogenation in Organic Syntheses" (1978and 1979). In the following paragraphs, the most recent hook will be reviewed and compared to the other monographs in the field, including B. R. James's "Homogeneous Hydrogenation" (1973) and F. J. McQuillin's "Homogeneous Hvdroaenation in Organic Chemistry" (19761.Rylander's "Catalytic Hydrogenation in Organic Svntheses" concentrates redom mi~" nantly on the heterogeneous hydrogenation. The homogeneous method is mentioned only occasionally, and usually only where the results of bath methods differ. A short chapter about how to carry out catalytic hydrogenation is followed by fourteen chapters systematically covering reduction of bonds and functions. Practically all instances of catalytic hydrogenations are discussed. Only very few of rather rare examples have been omitted such as the reducation of amides, nitroso, azo and diazo compounds,and of sulfur derivatives. Mechanism of catalytic hydrogenation is briefly mentioned where needed. Most of the discussions are centered around the suitability of a particular catalyst and reaction conditions for the reduction of a particular function, especially in the presence of other reducible honds or .. mouos. Soecial attention is dm-"rid to the selectivity and stereochemistry ~rfcatalytic hydroyenat ion and tu side reactions involved, s w h n i d < d , l r lwnd migratibns, rearrangements, and dehydrogenations. The enormous experimental material excerpted in the baok is well balanced and well organized so that it is not difficult to find the t v k of hvdroeenation for which one is look-
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experimental conditions, and by a large number of tables showing especially differences in the outcome of hydrogenations using different catalysts and different reaction parameters. The yields are listed in most tables and in some equations. However, most
Author
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Augustine Zymaikowski Freifelder Freifelder Rylander Rylander James
McOuillin
of the reaction schemes do not show the yields. Literary documentation is very thorough and testifies to an enormous amount of work on the part of the author. Quotations are spread evenly throughout the world literature with the emphasis on past-1950 publications (up t o 1977). References are listed alphabetically a t the end of each chapter. Because of that, a certain amount of attention on the part of the reader is needed to prevent mislocation of a quotation. The subject index, although comparable in size to indices of similar monographs, could be somewhat more thorough and more specific. Entries of more types of bonds and compounds rather than of individual compounds would be more useful. The layout of the hook is appealing. Suhdivisions in individual chapters are marked by distinct headings. This arrangement facilitates the orientation and contribute to the readability of the text. Formulae in the equations are nicely ~rinted;where necessary, conformations are shown. Misprints are extremely rare. A minor inconsistency is a haphazard use of CeHs and d for the phenyl group; P h would be more suitable since other matching Chem. Abstracts abbreviations are used throughout. An objection could be raised t o the use of the words dehalogenation and dehydrohalogenation in Chapter 13. While these terms commonly imply removal of elements or groups with the subsequent formation of multiple bonds, they are used here indiscriminately in the sense of replacing halogens by hydrogen. Rylander's hook, reasonably priced as it is, is an excellent contribution t o the bookshelf of a chemist involved in organic synthesis. Had instructions for laboratory procedures of typical hydrogenations been included, the hook would be completely self-contained. Without them, either Augustine's "Catalytic Hydrogenation" or Freifelder's "Catalytic Hydrogenation in Organic Synthesis" could be used as an ideal complement (since the Zymalkowski's excellent monograph is not widely available). Such a combination could save much time in the search for suitable reaction conditions of a typical hydrogenation. In conclusion, some data of the other existing monographs on the same topic are shown in the following table.
Year
Pages
References (approximately)
1965 1965 1971 1978 1967 1979 1973 1976
188 360 663 191 550 325 525 133
575 1035 3000 750 1720 1913 2064 280
Tables
Procedures
Index (pages)
8 0 0 1 68 58 84 10
29 450 0 50 0 0 0 23
19 20 3 2 48 13 15 3
Biochemlsiry: Mechanisms of Metabolism Eorlene Brown Cunningham, Medical University of South Carolina, McGrawHill Book Company, New York, 1978. x 767 pp. Figs. & tables. 17 X 24 em. $24.50.
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As the title implies, the emphasis of this text is on the mechanisms of the enzymes of the major metabolic pathways, principally glycolysis, gluconeogenesis, the tricarbovylic acid cycle and metabolism of lipids, nucleotides, and amino acids. Most enzyme mechanisms are discussed in terms of Cleland's nomenclature, often citing the crucial experimental evidence. A chapter on the level of Cleland's article in "The Enzymes" provides the background for this information. The chapters on bioenergetics, oxidative phuspharylation and photosynthesisare out of date in that they do not mention membrane potentials except to name the chemiosmotie hypothesis as one of three possible mechanisms. The synthesis of macromalecules also is treated very briefly. The first ouarter of the book discusses the physical techniques include many equations that see no further use in an otherwise nonphysical book. Same explanations are simply wrong, including the example of diastereotopic carbon atoms, the explanation of molecular weieht determination bv eel electrophure\is,anh t h e ' ~ i d e ; ~ l i l r n " O ~ l ~ ~ ~ r \ r . ' l ' h n ~.huirr 01 i h c m i ~ s l ro:wtions rmphnwrs i)nthr& rather than thaw rencrims that .arc of general use in biochemistry. For example, mechanisms of hydrolysis are discussed w h m t reference to the practical implic?lr i t m of rhr h i e lnl,ility of eaterr ampared t., nmidei or
