lws form of phenolphthalein on page 177 is incomplete. The resonance notation used in discussing the reactivity of chlomterested student can get a minimal warkbenaene is inadequ'ate and misleading. In ing knowledge of these subjeota by careful numerous places, one or more bonds have reading of this chapter assuming he has been, omitted, or extra bonds are added. taken at least one previous chemistry Given the relatively few structural formucourse. las in the manual, this large n m h e r of Each chapter contains many example errors becomes completely unacceptable. problems as well as additional problems In other plrtces in the manual, the ehemat its end. There are answers provided istry seems in error. For example, the to selected problems but not to all. The discussion of the reaction hetveen nindiagrams and tables are well done. hydrin and aspsrtic acid an page 135 sugThe author states in the preface "This gests that sspartic acid is converted to hook is written without apology for the acetic acid and two molecules of carbon student whose interest is in a field such dioxide, which is not at all the case. as veterinary medicine, agriculture, home The clarity of the discussion of principles economics, micro biology, dentistry, or is quite uneven through the manual. This medicine!' Later on he says " Some discussions are partkularly well text is not merely a watered down and done, while in others the presentation is edited version of a science majors text." overly terse and may leave the student This writer agrees with the author. Promore confused than informed The aufessor Ouellette has succeeded admirably thors need to take the time to speak to the in preparing s. readable text which will be student, to tell him in clear fashion what valuable for those people who do not need principles are involved, why it is imnor desire to be synthetic organic chemists portant to understand them, and then to but do need to understand the terminology develop clearly and precisely the orient* and the reactions of ba4c orgnni~group tion of the experiment. inga. It is duubtful that this rexr n.ould In summary, because of the large br urrful to the"Citi7en \'urer" who 11or.r number of errors in structural formulas, not have other scientific grounding; it is the apparent errors in fact in some of the this reviewer's belief that the text is chemistry, and because of general uhevenquite useful for the non-chemist working ness, I can not recommend this manual to in the m a s described above. its intended users. There are other manE. JONES uals now on the market which speak to the DONALD same group of students, do so with greateF Western Maryland College clarity and precision of style, offer a wider Westminster, Maryland 61167 range of experiments from which the instructor may choose, and are free from Experimental Organic Chemistry the kind of defects which so seriously detract from tbis manual. Raymond B . Seymour, University of WILLIAMH. BROWN Houston, and J m y G. Higgins, Illinois Bebit College State University. Barnes & Noble, 188 Beloit, Wise. 63611 Publishers, New York, 1971. x pp Figs. and trtbles. 23.7 X 16.8 om. $3.25. Compendium of Organic "Experimental Organic Chemistry" is Synthetic Methods written for use in a one-semester, terminal organic m s e . It contains a selection of Ian T . Harrison and Shuyen Hartison, rather standard experiments, ranging from Syntex Research, Palo Alto, California. those developing techniques (e.g., boiling Wiley-Interscience, New York, 1971. point, distillation, extraction, recrystalxv 529pp. 16 X 23.5 cm. $11.95. lisation) to several one-step syntheses The chemist who bad to carry out an (e.g., ethyl aeebte, cyclohexene, aeetorganic synthesis a few years ago relied on anilide, presoroylic acid, benzoic acid, Chemical Abstracts and Beilstein's H a d diethyl ether). In addition, the manual buch and then the original literature, presents a, number of experiments aimed at "Synthetic Orgsnic Chemistry" (Wagner developing descriptive chemistry of imand Zook, Wiley, 1953), "Organic Reaoportant functional groups. Each experitions" (Wiley), "Organic Syntheses" ment is designed in modular form, com(Wiley), and Theilheimer's "Synthetic plete with definition of terms, discussion of Methods of Organic" (Karger) plus a few principles, questions for pre-laboratory other specialized surveys. In recent years, assignment, and post-laboratory report however, his task has been made easier by sheet. the publication of such books as " R e Unfortunately, this manual does not agents for Organic Synthesis" (Fieser and deliver on the promise suggested in the Fieser, Wiley, 1967 and 1969), "Reaction introduction and must be faulted on Index of Organic Synthesis," a guide to several grounds. First, a large number of the Organic Syntheses (Sugasswa, and structural formulas are either poorly Nakal, Wiley, 1967), "Survey of Organic drawn or seriously incorrect. For exsmSyntheses" (Buehier and Pearson, Wiley ple, on page 133, the structural formula 1970), Annual Reports in Organic Synthelabeled ~ - ~ l ~ o e r a l d e h yisd ereally that of sis-1970 (McMurry and Miller, Academic ~glycericacid. On page 144, the polyPress, 1971), and now the "Compendium peptide chain of casein is drawn with Rof Organic Synthetic Methods." Although groups an the alpha carbons and on the there is some overlap in these various smide nitrogen atoms as well. And on the volumes, they are different enough in mme page, the structural formula labeled scope and/or argmiaation so that each is glutamic acid is in fact that of aspartic useful to the chemist, dependingupon what acid. The structural formula of the color-
book reviews
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information he needs. The "Compendium" is a compilation of about 3000 synthetic methods both old and new. A partind,!r type of trilnrformntion is ilI~srrxtedrhrough m e irr more cquarions, and Ihe yield srld a leudina reference viven fur each renctlon. Few vcrhnl ronirnmts are im*enred. The book is organized inlo .sections eorres~ondinulo all the rw~sihle interconversiohs am&g the major functional groups. An index table gives, for example, the page and section numbers where the preparation of amines from esters can be found. The page layout (structures, section divisions, etc.) is exceptionally well done. This reviewer recommends the purchase of this hook for the industrial and academic library and, considering its reasonable price, by the individual chemist. ~~
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LEROYW. HATNEB The College qf Wooster Wooster, Ohio 44891 Functional Groups in Organic Compounds Walter S. Trahanovsky, Iowa State Universitv of Science and Technolow. ~ r c n t k e ~ a l Ino., l, Englewood CI&, N. J., 1971. x 149 pp. Figs. and tables. 22.8 X 15 cm. $4.95, paper. 68.95, cloth.
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This mnst important member of the Prentice-Hail Foundation of Modern Organic Chemistry Series is theninth to he published of the ten volumes that the editor of the series suggests for use as the core of a one-year organic chemistry course. The book consists of three chapters of equal length dealing respectively with structure and nomenclature, physical properties, and chemical reactions of orgenic compounds. Chapter 1 provides a generally excellent discussion for rules of nomenclature making frequent use of tables for illustration of the rules. Problems for practice are given at the end of the chapter along with
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A490
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Journal of Chemical Education
encounterid in the - first-year brganic course that are not mentioned are heterw cycli~gand terpenes (to he covered specifically in later bpoks in the series) and amino acids and monosaccirhides which m e discrmed briefly in the first volume of this series, and which will presum&y be examined in greater detail in later volumes concerning naturally occurring materials. In the first third of the second chapter is presented a study of the correlation of melting point, bailing point, and solubility behavior with particular features of molecular structure. This is appropriate and unique to this hook of the series and is, even though the author has made some weak analogies relating molecular behavior to macroscopic phenomena of every-day life, a good discwian of the subject. The remainder of the chapter provides brief but lucid descriptions of the theory of glc and uv-vis, ir and nmr fipectroscopy and how they can be used for functional ggrup analysis. Although these topics are also discussed a t length in other volumes of the series, the explanations found in this book
tional groups and subgroups which makes the hook so uniquely valuable for quickly scanning many examples of a, class of compounds to see the gradual (or marked) change whioh occurs in the ir absorption with change in structure. Of course, in addition to this study use, the book would be essential as a. basic compilation of spectra, for the smaller library which cannot afford a comprehensive collection such as Sadtler. In my opinion, an hour or two of browsing in the "Aldrich Library" gives a better impression of trends and variations in absorption bands for various types of compounds than many hours with exeellent texts of the Bellamy or Nakanishi type. Obviously, the best procedure is to use the Aldrich volume along with such descriptive or theoretical books. However, the well-known ir texts just do not contain enough spectra, and they are too scattered in Sadtler's invaluable collection, to show the student-reader exactly how absorption bands change with the introduction of suhstituents a t a number of different locations dawn a chain or on s. ring. There is a molecular formula index for all compounds (misnamed Empirical Formula. Index) to increase the utility of the volume. I have found it helpful to ignore the index when I am looking for a. specific compound which is probably among the 8000. The search is still relatively quick because the compounds are listed in order of increasing molecular weight and then complexity within each class. The bonus is a few more moments of seeing a series of Dnvm J ~ R D . A N spectra of the general type of the comSUNY-Polsdam pound I am looking for, and thus a bit of flew York review in the continuing fight against memory-entropy.
of how eleotromagnetic radiation is absorbed by molecules in these spectroscopic methods are superior. Particuldy good is the section on the origin of nmr chemical shifts. The find chapter is a survey of various reaction types, often including mechanisms. The reader is frequently referred to the various texts in the series that describe particnlar subjects more extensively. Both Chapter 2 and Chapter 3 provide a t their conclusions numerous and a p propriate problems for student practice. Here also in both chapters are lists of references (books not of this series), only one of which, however, if footnoted within the text. Throughout the boak the author makes extensive reference t o other books of t,his series, some of them not yet published. This is a questionable and potentially misleading practice; this perticular hook was referenced (attributed t o another author) in other volume.? of this series six years prior to its publication! The first two chapters have definite value for supplementnl purposes. Chapter 3 serves best as an introduction to other books of the series Before selecting this hook along with others of the series to compose a core of textbooks for a year course in organic chemistry, one should examine d l t o avoid selecting any one that appreciably duplictltes others. This is most important if one considers that the price per page of this series (paperback) is approrimatelv three times that of the most popular cloth-bound organic texts.
The Aldrich Library of Infrared Spectra
Charles J . Pouehert, Aldrich Chemical Co., Ino. Aldrich Chemical Co., Inc., 1203 pp. Milwaukee, 1971. xxiii 31 X 24.5 em. $44.50.
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When I first saw an advertisement for this hook, my reaction was, "Who needs another boak on or about or with ir spectra?" So I didn't order i t for our library or even want to look a t it. Now that I have seen "The Aldrich Library.. .," I have to answer thst initid question, in some embarrassment, "Every library which treats organic chemistry-college, university, or industry-needs it. And a t $44.50, it is the greatest bargain in chemical publications today; most individuals involved in organic would do well to forego a. few other hooks to have their own individual copies." The basis for that radical revernal is simply examination of the "Library." I t contains 8000 spectra (625 to 4000 om-' range, 95% from a Beckman IR-8 grating instrument) on some 1100 9'/4 X 12 in. pages. But far more important than the number of spectra or the convenience of handling the big book is its arrangement. The spectra are printed eight to a page in 50 functional types ranging from NonAromatic Hydrocarbons through Organometsllic and Arsenic Compounds with each major type sub-classified in as many as 15 categories. I t is this ordering in func-
many students in this country would welcome its self-teaching a5peets. Nevertheless it can be used for student assignments.
8. J. BERNARD A. FIEKERS, College of the Holy Cross Worcester, Mass. 01610
Inorganic Titrimetrie Analysis. Contemporary Methods
Walter Wagnw, University of Detroit, and Clarence J . Hull, Indiana State University, T e n e Haute. Marcel Dek22.5 ker, Inc., New York, 1971. xii pp. Tables. 24 X 16.5 cm. 513.50.
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In the space of only 225 pages this little book attempts t o act as a "rapid and convenient guide" to the select,ion of x titrimetric method suitable for the occasional determination of an element ~ ~ i rel* n g tively ordinary equipment. Itsstated aim is t o circumvent the purported difficulties of obtaining this information from the extant literature. Titrimetric methods for seventy nine elements and their compounds are included, arranged according t o the Main Groups of the Periodic Table. A standardized format is used for each element. This hegins with s. Synoptic Survey consisting of a few sentences of text under subheadings of Classical lMethods a.hd Contemporsry Methods. Methods published prior to 19.50 are relegated to the Classical category. There is then an Outline of Recommended Contemporay Methods for the element in question, which in most ca5es occupies only a page or two. Thc treatment concludes with a. few (generally less than ten) literature references, most of which are to journal papers published FRANK L. LAMBERT since 1960. Occidental College I n keeping with the restricted aim "to Los Angeles, California 90041 ~ r o v i d esufficient information for readers to decide whether agiven method of anelysis might suit their needs . . .," only the skeletal principles of the selected titriProblem Solving for Chemistry metric methods are described. In most eases, in order to employ the methods, the Edward I . Peters, W e ~ Valley t College, reader will need to consult the cited literaSaratoga, Calif. W. B. Saunders Co., ture for experimental details. Although Philadelphia, 1971. ix 320pp. Figs. space was too limited for comprehensive, and tables. I,? X 2 2 3 em. Softhomd, 84.7.7. critical comparisons of the methods, in many caqes one does find statements about This paperback is auto-tutorial. I t is such important matters as interferences, complementary t o 'Chemical Principles" suitable sample size, accuracy, ete. The by Masterson and Slowinski. Thus it cnn selected methods emphasize physicosave the professor timein teachinguChemichemical techniques of end-point deteccal Principles" or other suitable texts due tion, such as potent,iometry, amperometry, to its auto-tutorial chmxter. spectrophotometry, etc. Coulometric tiI t contains 17 chapters, 7 appendices, 7 trntion methods are included. I n the case page answer section with answers to about of metal ions, the newer complexometric 2.70 problems, an index of about 27.7 items titrations employing ethylenedisminetetraand an the inside covers a periodic table acetate (EDTA), and analogous complexand a table of atomic weights. ing titrsnts, are well represented. Its method is thst of dimensional analyIn same cmes the authors seem t o havc sis. Examples are developed carefully, been carried away a bit by their enthusiprogressively, and almost micru?copicelly asm for "contemporary" as distinct from throughout the chapters. In each chapter their definition of "cla4cd" techniques this part is followed by problems. (pre-19.50). For instance on p. 40, in conThe suhiect matter is about that usuail~ nection with the titration of +2 mercury with thioeyanate ion, a recommended method employs high frequency (oscillametric) end point detection. This recal topics. quires more highly specialized instrumenThe text is commends,ble for the exper(Continued on page A48B) tise that went into it. One wonders how
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Volume
49,
Number
9,
September
1972
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A491
