book reviews
uct chemistry. However, even in compounds not derived from natural sources, an etymological origin may be found in the name; thus, in ambenzene and in diazomethane the prmenc P of nitrogen is dcnorrd by the fragment .an,-, der~vedfrom the Greek, and ultimatrly denuting the fact rhar elemental nitrogen does not support life. These two time-honored methods of naming eompounds are being displaced by a third, which is derived from the desire of the indexer and the cataloguer for a unique name, absolutely devoid of ambiguity and alternative. The number of chemical campounds is so large (currently about four million), and the use hy chemistsof abstracts bf the chemical literature and indexes to i t so frequent, thnr rules for nomenclature put tugether hy urganimions (CASI which pn,. dure such nuhlirnr~onsarc diaolacine t h ~ a e not. put forunrd hy hxlw t1111'~~iwhich'ho ('hem~stsalrrady have a spuken "dialect." hut a written "official" language (here, (:AS nomenclature) also existx we can no longer write aniline, hut we must use henzenamine, and similarly trimethylamine must give way to N,N-dimethvlmethanamine.T o comolicate the situatkn further, even the official language is changing: CAS is continually revising its rules of nomenclature, giving rise to differences, for example, between those used in 8CI and 9CI. The book reviewed here is sprinkled with comparisons and contrasts between CAS and IUPAC nomenclature and contains a useful appendix devoted t o such differences. The f a d that the first author is English (ex-editor of the Journal of the Chemical Society, and a member of a IUPAC Committee on the Nomenclature of Organic Chemistry) and the second is American (Professor Emeritus a t Oklahoma State University, and section editor of Chem~ealAbstmets) has also led to the inclusion of comparisons of nomenclature in the two countries-English usage in this respect having heen modified by the licensing there of the use of CAS materials in the UKCIS project, and hy the fact that there are more American textbooks in chemistry than ones of British origin. If Sherloek Holmes were living in 1980 he would not (or should not) exclaim as he did over the hisulphate of haryta, hut rather over barium hvdroeen . .. sulfate. In the first osrt of the text, one finds numerws !nreresrmg e x amples from inorganic rhemiitry of how oldrr n~,menrlnturehas heen mdifipd, and how nomenclature has also been coined to deal with new types of structures. Walframates and niecolates (IUPAC) may startle some, while the now universally-recommended spelling of "sulfur" may reassure others. A third group of readers may have to study newer terms such as "closo" and "nido," and the use of the letters I ) and A. The book contains several highly useful tables (e.g. of affixes used in nomenclature, names of acids, and abbreviations used in naming ligands in inor~aniccomolexes) which facilitate its use. a n d i h e inde; is generally well organized; though a list of tables would have rendered it even more useful. The section on the nomenclature of organic compounds is about four times as long as that devoted to inorganic compounds. This second part starts out very well with a good diseussion of the approach t o a name, and of the classes of organic chemical nomenelaturehere denoted by the terms substitutive (chlorohenzene), conjunctive (2-naphth~
Health and Safety Guldellnes for Chemistry Teachers Kenneth M. Reese, American Chemical Society, Department of Educational Aetivities, Washington, DC, 1980. 15 pp. 20.9 cm X 28.6 cm. Single copies free; 2-10 copies $1.00 each; 11-100 copies $0.75 each; 101 or more, $0.50 each. The debt we all owe t o the ACS Department of Educational Activities and t o its inspiring leader, Moses Passer, could never have been fully paid prior t o the end of 1979. Rut now, in a single stroke our debt is increased a hundred fold, a t least. Those of us vears involved in Ishwho have soent man". , oratory safvty nnd health protwrior know huw mporrnnr and rscntial thii tupic i, for all our colleagues. At last, a comprehensive introduction addressed directly to those who need the information is available for only the cost of a phone call or stamp plus a hit of time spent reading it, and hours and hours of implementing it. (On p. 9, sentence 2, it says, "Who will pay the costs of support for those hours and hours of implementation?") Four of the five chapter titles are questions: "Who is responsible for lab safety?" (You are, hut so are some other folks.) "How do OSHA and NIOSH affect chemistry teachers?" (Constructively.) "When is the teacher legally liable?" (Rarely, if you've heeded this book.) "How does one set up a lab safety program?" (From p. 9-Not a t all unless you get full commitment from the top administrative level.) And, Guidelines for safety programs. Short reviews are probably more likely to he read, and a lot more likely to be heeded, especially when the hook under review is free of cost. Get a copy, now! Jay A.
Young
Chemical h4anufacfurersAssociation
lntroductlon to Chemlcal Nomenclature
R. S. Cahn and 0. C. Dermer, Butterworths, Wohum, Massachusetts, Fifth Edition, 1979. ii 200 pp. Figs. and tables. 22.1 X 14.0 em. $27.50.
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"Must a name mean something?" Alice asked doubtfully. "Of course i t must," Humpty Dumpty said with a short laugh: "my name means the shape I am-. Chemists often name substances according totheir properties or reactions. Picric acid is acidic enough t o react with certain metals, and with bicarbonate, yet it contains no carhmyl group. Should it he called an acid? Similarly, mast organic chemists would argue that i t is easier to visualize the reactions of tertiary hutyl chloride if it bean that name, than if i t were called dimetbylchloroethane. On the other hand. the oriein (immediate or ultirnatei of a substanre may olso play o rolr in naming it,rsprr~nllyin nattrrnl prod-
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A296 1 Journal of Chemical Education
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aleneethanol), mixed (methoxyearbonyl), and subtractive (use of prefixes such as dehydro, nor, and anhydro). Other sections are devoted t o a wide variety of topica with which nomenclature must deal, including absolute configuration, relative configuration (some passible surprises here), isotopic substitution, indicated hydrogen (e.g., in 3H-fluorene), polymers, enzymes, and other natural products. A quoted statement (p. 119) that the nomenclature of cvclie ketones is a semantic disaster area eives rise t o a well-docomanted ~-~-..and persuasive section. Further troublesome topics which are discussed include the manner by which CAS and IUPAC (differently) choose the longest chain in acyclic compounds (pp. 57-58), and others such as the names of amino acids (p. 107), the nomenclature of the SHerouo . (o. . 123). and thenomrnclafure of cyk,phanes tp. 901. which is ~ r r e n t l vunder study hy IUPAC.'l'hesection on heterocyclic cmnpc,unds is ncll writtm and especially useful. The review copy contained a few printing errors (p. 65, two strange suhstituents; p. 87, a benzene ring portrayed as a cycloherane ring; p. 147, a misnamed figure 51A) and some puzzling or unclear passages (p. 88, multispiro systems; p. 113, two statements on carholactones; p. 120, hydro-0x0 s y s t e m in cyclic ketones), and pp. 126127 read as if the authors had not communicated well. On p. 127 we are left in suspense over the mention of alleged further problems with indicated hydrogen; some references-usually well supplied in every other chapter-would have been useful here. Chemical nmnenclafure issuchacomplex subject that any inrroducrion tuit whirhaeriously attempts to face up to the requisite demands is very welcome. This reviewer helieves that the h w k does indeed meet the task and recommends it t o all who are interested in following the ways in which contemporary demands affect our decisions on how to name compounds most wisely. The price of $27.50 is high, hut the book is worth it. "When I use a word," Humpty Dumpty said, in a rather scornful tone, "it means just what I choose i t to mean-neither more nor less." "The question is," said Alice, "whether you can make words mean so many different things." "The question is," said Humpty Dumpty, "which is to he masterthat's all." ~
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J. E. H. Hancock Reed college, Pwtland, OR 97202
Huckel Molecular Orbital Theory
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Keith ~ i t e s Academic , Press, 1978. v 371 pp. Figs. and tables. 23.5 X 15.5 cm. $32.00.
The author's intent is to present a simple, descriptive, and ss nonmathematical as possible introduction to the Huckel molecular orbital (HMO) method and its applications to organic chemistry. This concise and
