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-
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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
