book reviews Editor: W. F. KIEFFER College of W-ter
W ~ ~ l t s Ohio r,
Organic Chemistry
Norman L. Allinger, Univemity of Georgirt, Athens, et a?. Worth Publishers, 1007 pp. Inc., New York, 1971. xxi Figs., and tables. 19 X 28.15 cm. 515.95. For several years instructors of organic chemistry have had an excellent and wide selection of texts for their courses. These texts have encouraged organization of the courses generally dong one of two different patterns, namely, the functional group and reaction type approaches. Recently, nearly all of the well-established texts have been revised extensively to bring content and style upto-date. Nonetheless, an interesting new text for the first year course in organic chemistry has been produced by B relatively large group of authors. "Organic Chemistry" by Allinger, Cave, De Jongh, Johnson, Lebel, and Stevens deserves careful attention far several reasons. It was written by respected organic chemists whose research and teaching interests range across most of the field. I n addition, a quick glance a t the hook reveals that the printing, figures, illustrations and t,aMes are verv well done. A careful reading also indicates editing of equally high quality for there are very few factual or typographicd errors. The authors claim in the preface that organic chemistry can be more easily and
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effectively taught by establishing E structural and theoretical frrtmework before proceeding to the reactions of organic compounds and their application. Thus, this book strongly resemh1es"Organic Chemistry" by Hendricksan, Cram, and Hammond in general outline. The first thirteen chapters deal with the structure of organic compounds, the next ten chapters discuss reactions, and the last thirteen chapters cover a. variety of topics; these include synthesis, polymers, compounds of biological importance, organosulfur, organosilicon and organophosphorus chemistry, spectrometric methods, and industrial organic chemistry. The authors make little or no effort t o provide an experimental basis for the current theoretical frrtmg work of organic chemistry which they use as an organizational scheme and a point of deperture for discussing the chemical hehmiovior of carbon compounds. This may be apoint of concern for someinstructors. I n my opinion, "Organic Chemistry" by Allinger and coauthom is the most authoritative, comprehensive text currently avsjlsble for the first course in organic chemistry. The discussions of structure, techniques (e.g., ir, nmr, uvvis, mass spectrometry), and reactions and their ~pplicatiousin i t equal or surpass their counterparts in other texts in accuracy, clarity, and depth. The problems a t the ends of the chapters appear t o be
in this Issue
Noman L. Allinger, et al., Organic Chemistry Robert J. Ouelletle, Introductory Organic Chemistry Raymond B. Se~rnourand J e r y G. Higgins, Experimental Organic Chemistrv Ian T . Harrison and Shuyen Harrison, Compendium of Organic Synthetic Methods Walter S. Trahanovsky, Functional Groups in Organic Compounds Charles J. Poucherl, The Aldrieh Library of Infrared Spectra Edward I . Peters, Problem Solving for Chemistry Waller Wagner and Cla~enceJ. Hull. Inorganic Titrimetrio Analysis ~antemporilryMethods Klam H. Altgelt and Leon Segal, editors, Gel Permeation Chromatography R. Bunt and C. Ponnamperuma, editors, Molecular Evolution I: Chemical Evolution and the Origin of Life Gary E. Means and Robert Feeney, Chemiod Modification of Proteins Robert B. Fischer, Science, Man and Society John McMurlurnr and R. Brvan Miller. Annual R e ~ o r t in s Synthetic Chemistry, i970 Morris Goran, The Future of Science Dietlich Jentzsch, Gas-Chromatographie, Grundhgen-AnwendungMethoden Gmelin-Durrer The Metallurgy of Iran L. F. Haber, The Chemical Industry During the Nineteenth Century Ivan G. Draganic and Zorica D. Draganic, The Radiation Chemistry of Water New Volumes in a Continuing Series
carefully choaen t o aid in study and understanding of the material. There are problems also interspersed throughout each chapter t o encourage and reinforce a questioning, thoughtful sttitude by the student toward his study. There is only occasional evidence of unevenness of level or style. However, the book clearly expects considerable chemical background and maturity of the student. For example, little discussion is devoted t o acidbase theory or t o atomic structure. I n contrast to instructors.. manv.. of whom will f i l d thi? text cxtremrly nttmrtiw, nlwt students will prohahly still prefer a lwli dem~nding text organized aruund furm tionsl groups. The only discernible deficiencies in the vorltent of thia text arlre no douht from limitations of space. The book I I I V I U ~ P S 1007 . wars. - I wnlld have nrrferrrd more information on molecular rearrangements and the application of symmetry principles to organic reactions. I n addition, a brief discussion of metal ion crttdysis of organic reactions wauld be both interesting and valu~hle. And same instructors may find that the chapter on reactions of alkanes (Chapter 23) appears later in the text than they would like. Indiana University-Purdue University at Indianapolis, Indiana Introductory Organic Chemistry
Robert 3. Ouellette, The Ohio St& University. Harper and Row, Publishen, 429 pp. New York, 1971. xiii Figs. and tables. 23.5 X 15.5 om. Softbound. $7.
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Those familiar with Professor Ouellette's earlier text "Introductory Chemistry," (Harper Row, 1970) will find that this text is an extended version of the several chapters on organic and biochemistry found in it. As s n example of the added materid, the new text has 349 pages devoted to the subject while the older one has 231 pages. The new text deleted the earlier chapter on lipids, however, so that for comparison purposes 217 pages of the first text is devoted to organic and biochemistry. Since the page snd type size are the same, there is approximately 75% additional material added in the form of tables, examples, and explanations. There is only little rewriting. The chapter on stereochemistry is the only one which did not have additional material added. (For comparison purposes see chapters 16 through 25, 27, and 28 of the older text.) Chapter 1 of the new text entitled Structure and Properties is essentially a revision of the old chapter 6. This revision was rtccomplished by deleting material related to inorganic chemistry and adding additional information about carbon chemistry including functional ggrups, structural isomerism, and several new diagrams which helo to elarifv " hvbridi~ation. , Chapter 2 h e r n i a Kenrtions, is a condensed form of rlre materinl previounly cont,linrd in (.'haprrr& 9, 10, and 11. Thiq chapter is meant by the author to be basically review material on equilibrium, acids and bases, and redox, hut the in(Continued on page A490)
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Volume 49, Number 9, September 1972
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A489
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
