have attempted to computerize data bases involving reactions between three-dimensional molecules have discovered, the prohlems of representing structures and developing suitable algorithms for reactions are formidable. Although the author of this program has made a good start a t developing some of the codes and algorithms, the program does not yet meet its stated goals. Whatever it is, it is certainly not an "easily consultedversion of s textbook". I found the program of little value for my own use in its present form, and I would not distribute it to an organic chemistry class because of ambiguities and errors in the program and accompanying documentation. Several examples illustrate the earelessness with which the documentation was put together. The manual begins with the ststement (?) "This program is designed to show you a wide range of organic chemicals react and under what conditions." Under the section entitled "Hands an," the first example given is the reaction of 2-chloropropionic acid with ethanol. Under the name 2-chloropropionic aeid is drawn the formula for 3chlorohutanoic acid with a pentavalent carbon a t C3! On the next page of the manual, the user discovers that the structure being entered is really 3-chloropropionic acid. After the two reactants (3-chloropropionic aeid and ethanol) are entered into the computer, the first product suggested by the program is 3-ethanypropionic acid, the product of a Williamson synthesis of ethers in the presence of sodium hydroxide. The students who tried this example were (rightly) confused about why the ethoxide did not simply deprotonate the carhoxylic acid. The algorithms used to determine what constitutes a "correct" reaction are simply not sophisticated enough to make this program useful pedagogically. For example: The program lists one of the productaof the reaction between chlorohenzene and benzene in the presence of aluminum chloride as biphenyl and refers the user to the appropriate page in Morrison and Boyd, which states unequivocally that Friedel-Crafts alkylation does not work on aryl halides. In the addition of HBr to l-propene in the absence of peroxides, the first product given by the program is l-hromopropane. After the product is shown, a help window appears which explains that inMarkovnikov Addition, "the hydrogen of the acid attaches itself to the carbon that already holds the greater number of hydrogens". The second possible reaction that is shown is the correct one, 2-hromoprapane. In the addition of bromine to 2-hutene, the organic product is shown as 2,3-dihromohutane, with no mention of the stereochemistry of addition involving an intermediate cyclic hramonium ion. I could find no way of specifying cis- or tram-2-hutene as a starting material. The addition of bromine in water to an olefin makes no mention of either the regiochemistry or stereochemistry involved in the reaction. The addition of hydrogen to l-pentyne gives l-pentene as a product with the necessary "environment" requiring Pt,
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A130
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of Chemical Education
Pd, or Ni. No differentration is made between the catalysts used fm hydrugenation of olefins and alkynes. Sodium ethoxide and many other ionic reagents are not included in the data hase, making it very difficult for an introductory organic student to practice nucleophilic substitution and elimination reactions. Users could, of course, add such reagents to the data hase. In summary, I cannot recommend this program in its present form. If the data hase were considerably expanded, and if some mechanism far taking into account the stereochemistry of reacting molecules could he introduced, the program would serve a useful purpose. Tremendous advances have been made in the last five years in the computer representation of three-dimensional chemical structures. Perhaps an attempt could he made to couple some of the useful algorithms contained in this program with a more sophisticated approach to entering and graphically representing the three-dimensional structures of reacting molecules. Peter G. Mahaffv
The chapters on organic and hiochemistry cannot he faulted as to the choice of material or the coverage of the material. The coverage of the general chemistry material is not as well done. Chapters 1(Matter, Energy and Measurement) and 9 (Nuclear Chemistry) seemed especially well written for a tent of this type. If there is a weak chapter, then it must he chapter 7 (Reaction Rates and Equilibrium). If there is a topic that was relatively neglected, then it would he thermodynamics which, in general terms, would he useful to students. Does this text attain the goals its authors set forth in the orefaee? We think it does. It especially attains the goal of msintn~ning student interert while cwering n, many ditierent chemical topics. We assume thnt the text will he used for a two-semester sequence. We heartily recommend this text for its intended audience. David E. Horn and Lewis A. Walker Goucher College, Towson. MD 21204
Chemistry: A S c i e n c e for Today H. Stephen Stoker. MacMillan: New York, NY, 1989. xi 884 pp. Figs. and tables. 20.8 X 23.9 cm.
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Iniroduction to General, Organlc, a n d Blochemlstry, S e c o n d Edltion Frederick A. Benelheim and Jerry March. SaundersCollege Publishing: Philadelphia, PA. 1988. xxix 633 pp. Figs. and tables. 20.5 X 26 cm.
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Writing a text for such a broad range of chemical topics is an ambitious undertaking. Overall, we would say that the authors did a tremendous job with this text. In any such hroad-ranging text there must he choices of what to include and what to omit of the material usually covered in standard courses assigned to this range of topics. The choices of one teacher would not he the same as those of another The choice- these au. rhors have made would appear tu be about deal, especially for a c l a r ~ o highly f talented students. The physical appearance and first impression made by the text is excellent. The text is easy toread. The photographs are not only handsome hut also they are appropriate teachine tools as are the comments made in the attractive wide mareins of na~er. -- the .-~. r-m... The boxed sections of material are well done and helpful to student understanding. Review and key term sections a t the end of each chapter are another plus. The prohlems at the end of the chapters are well arranged according to the material covered in the chapter, and there is asection of starred problems that are more difficult and arranged randomly according to materialwell done! There is a good index. The answer section is necessary, hut the authors resisted the temptation to answer all the questions and left some to test the confidence of the students. There is a good index, hut a few appendices containing tables of data would he a welcome improvement.
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Chemistry: A Science for Today is divided into three sections and 24 chapters. The first section consists of seven chapters and is dedicated to the classical inorganic topics such as handing, balancing of equations and mole problems. The second section, with three chapters, deals with the properties of the states of matter, including gases, eolligative properties and acid-base behavior. The last section has 15 chapters and is dedieated to the "chemistry in the modern world", including four chapters in inorganic descriptive chemistry, one chapter in nudear chemistry, three in organic chemistry, two in hiochemistrv. .. and two in oollution. Given the topics presented in the third section and itz magnitude compared tcr the frrst two RCCtioni, it seems hrical to have divrded it into two sections, one dealing with organic and biochemistry, and one dealing with deseriptive topics in general. The author achieved his objective of writing a text "primarily designed for a oneterm course.. .for nonscience majors". This hook is well written, at the correct level for a beginning student, is very clear in the concepts and ideas presented, and is not verbose. The author's apparent secondary oh.to provide a foundation for furjective, ther study in chemistry"is also achieved. To do this, he covers the topics to a greater depth than necessary in a one-semester terminal course hut does not burden the student with superfluous material. This reviewer feels that an instructor can easily adapt the hook to either of the objectives by skipping sections or by slightly supplementing the material. I t should he mentioned, though, that some of the concepts in this hook are presented in a very succinct fashion, such as dynamic equilibrium, which only takes six lines p. 239. But, even this brevity is
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commendable, because the topics are mentioned, very short explanations of the concepts are given (which can be expanded further by the instructor if so desired), and the length of the book is kept a t a desirable level, 861 pages. His treatment of quantization is novel and worthy of use. The periodic table furnished on the inside front cover contains 109 elements, and it has the correct A and B headings. I t is unfortunate that some other topics such as VSEPR Theory and limiting reagent (almost done on p. 203) are not covered even in a rudimentary fashion. Double and triple bonding are covered, but there is no mention of sigma and pi bonding and there is no orbital picture to enhance the understanding of this important topic (only a ball-and-stick model much later, p. 508 and p. 513). One very specific drawback is the complete absence of S I units in this book. Even in relation to heat, the author clings to the now outmoded use of calories. The descriptive material is treated in the third section of the hook under a large variety of headings such as water, me&, nonmetals, personal care products, and fossil fuels. The specific topics covered include hard and soft water, allotropes, makeup formulations, marijuana, and sulfuric acid, among many others. The diversity and depth are adequate. The author enhances the pedagogical value of this descriptive material by making enough cross-references to the corresponding theoretical material. The book is not fancy. The cover is multicolored and hrieht. The text itself is in hlack and whrte with pffectiw highlight ofthedefinition* in heige cdor. The pictures and diagrams are appropriate and of varying shades of these same colors. The diagrams parallel the text and are designed to enhance the student's understanding. Historical profiles of about 20 scientists (surprisingly not that of Watson nor Pauling), each about one-half naee in lendh. .. . are inters~ersedthrouehout the book, adding aperrmal dimension cu it. The author stater that there ir supplemental material available, including the answers to all the questions and a test bank. These materials were not available to me for review. The book is particularly free of typagraphical or conceptual errors. Juan F. Villa M e r t H. Lehman College of me City University of New Yo* Bedfwd Park Boulevard West
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Organlc Chemislry Douglas J. Raber and Nancy K. Raber. West: New York. NY. 1988. xix 1445 pp. Figs. and tables. 19.5 X 26 cm.
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This text is written for a full-year first course in organic chemistry. The material is divided into 27 chapters, using the functional group approach. Worked examples and exercises are found within the text, and there are numerous problems a t the end of each chapter. Also found a t the end of most chapters are useful sections entitled "Terms
and Definitions" and "Summary df Reactions". No solutions to the exercises and problems are given: if smwers are desired, the "Student Sulutions Manual and Study Guide" must be purrhared. The authors indicate in the preface that the Instructor's Manual contains full literature citations for all reactions included in the text. This should prove to be very handy on those occasions when instructors wish to add a little something extra to their lectures. The lawut apppars to haw been carefully and thuuahtfully deqigned. Figures and re. action schemes are will drawn, using only two colors, red and black. No errors were found durine this review. Most of t6e material which an instructor of introductory organic rhemistry would l i k e t u r u w ran he found in this book. However, the topics whieh the authors choose to emphasize, and the order of presentation should be closely examined by anyone considering adopting this book for classroom use. Some of the topics which filled the pages of organic teats in earlier years (e.g. soaps, detergents, fats, oils, phenols, am dyes) are barely mentioned, and in their place are discussions of frontier orbitals, multistep syntheses, and carbon-13 NMR. Chapter 10 covers aromatieity and the structure of benzene in 22 pages, and then spends only 12 pages on a partial treatment of electrophilie aromatic substitution. This latter subject is continued in Chapter 18. The acidity of carboxylie acids, including substituent effects, is covered in Chapter 4. Twelve chapters later we find the remaining material on acids. Reactions of alkenes are in Chapter 5, except for polymerization, which is in Chapter 25. The Diels-Alder Reaction is not covered in the chapter on dienes, hut rather at the end of the book in a chapter entitled "Organic Synthesis Using Polyfunctional Compounds". Topics of biochemical interest receive adequate coverage, although again, the order of presentation is a little unusual. For example, there is no chapter dealing in the traditional way with amino acids and proteins. Amino acids and peptides are in Chapter 20, nueleic ac-. ids are found in Chapter 25 along with other natural polymers such as rubber and cellulose, and manmade polymers such as nylon and polystyrene, and purines and pyrimidines are in Chapter 24, along with other heterocyclic compounds. I t is curious that these closely related biochemical topics are discussed in three separate places, whereas unrelated systems are brought together in the polymers chapter. I t is this reviewer's minion that the first 21 rhapters are well written, with content and CwI of presentation quite satiufart~ry for the intended audience.'l'he mnphssis un more modern topics, the near omission of some of the old favorites, and the order of presentation will receive mixed reviews. The last six chapters will not prove to be so useful. Part of this material, such as polymers, should have been ineoroorated into the first 21 chapters, hut acreat deal could haw been left out withcut doing h m n tgr the buok. At six pounds, it is far t w heavy anyhow' Harold M. Bell Virginia Polytechnic InstlMe and State University Blacksburg. VA 24061 ~~~
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Mechanism a n d Theory In Organic Chemistry, Thlrd Edition Thomas H Lowry and Kathleen Schueller Richardson. Harper a Row: New York, 1987. xi1 1090 pp. Figs. and tables. 24 X 19 cm.
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In the second edition of this popular introduction to reaction mechanisms in organic chemistry there was a substantial change in the format of the teat relative to that in the first edition. In this, the third edition, the changes are less obvious and appear to be directed toward clarification and more precise definition but do include the expected expansion to include recent findings, revisions, and corrections of previous materials as well as a limited number of new subject areas. The review of the second edition by K. D. Berlin (this Journal 1982, 59, A1431, with only a few changes, would apply equally well to this edition and should be read by prospective purchasers. Aceording to the authors' preface, changes in the new edition include coverage of Hiickel molecular orbital theory, an overview of the approach taken by semiempirical and ab initio calculations, a discussion of solvent isotope effects, expansion of the treatment of gas phase processes to include uucleophilic substitution and elimination, introduction of Marcus and Pross-Shaik models of reaetion coordinates, expanded treatment of electron-transfer mechanisms, expanded discussion of triplet state carhenes, an introduction to electron-spin resonance, and a revised treatment of chemically induced dynamic nuclear polarization (CIDNP). Page by page comparison of the two editions suggests that the authors have been modest in their claims. Thus, for example, this reviewer finds Chapter 4, Aliphatic Nucleophilic Substitution, and Chapter 12, Photoehemistry, to have been rather thoroughly revised. The third edition is approximately 100 pages longer than the second, and, although some text from the second edition may not have been reset, it appears to this reviewer as though in general there may be slightly more text per page in the new edition. Although some material has been deleted, the amount of such material is not large. To most, but not all, chapters a reasonable number of new problems have been added. The copyright date is listed as 1987, and the text was made available for examination early in that year. Thns, the manuscript was probably completed sometime in early 1986. In accord with this speculation are the latest dates for references (1985) in the text. As recent progress in physical organic chemistry and in reaction mechanisms has been generally thought to have been less vigorous than in previous decades, it is not surprising that the number of recent references is relatively small. Even so, progress is being made; thus, some of the discussion in the text may not represent either the latest thinking or the degree of controversy still existent because of research reported since the book was completed. Thus, discussions of single-electron transfer reactions, of the stereochemical considerations in the addition of arganametallic or hydride reagents (Continued on page A132)
Volume 66
Number 4
April 1989
A131
