book reviews Editor: W. F. KIEFFER College of Woorter Wooster, Ohio
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure or mechanisms proposed for that type of reaction, followed by a discussion of orientat,ion and reactivi1.y in t,erms of the usual parameters; substrate, solvent, ete. Then n large number of example8 of each rcacProfessor March has written a text tion t,ype are discussed. The sequence of aimed a t the second course in organic reactions follows a logical pattern wherever chemistry a t the undergraduate level possible and each reaction is given a code ~ . ~ ~ n for > i ~vro.,< c r wft,rrncr. and/or the survey course in organic chemistry a t the graduate level. In the text For exnmplr i n Chapter 15, Arlditim tu he covers three major areas; the structure ('~rbon-('ml>on11td111)IcI h d s rv.wtit,n~ of organic compounds, the reactions of in which hydrogen adds t o one side of the these compounds, and the mechanisms double bond is a main heading. In sobb y which thereactians take place. headings are the reactions in which haloThe hook is divided into two parts. gens, oxygen, sulfur, nitrogen, hydrogen, The first six chapters of Part One deal boron, and carbon add to the other side of primarily with aspects of the structure of the double bond. The second main organic compounds. Included in this heading includes reactions in which hysection are the topics of bonding (localdrogen does not constitute one of adding ized, delocaliaed, and weaker interactions), moieties. Reactions in which halogens, stereochemist~y (opt,ical isomerism, geooxygen, nitrogen, and carbon add to one metrical isomerism, conformational analyor both sides make up the sub-headings. sis, and the consequences of ring strains), Thns this chapter includes such diveriie reaction intermediates (carhoninm ions, topics as electraphilic addition reactions, carhanions, free radicals, and carbenes), catalytic hydrogenation, t,he Michael and instrument,nl met,hods for deterReaction, and the Diels-Alder Reaction. mining struet,nres. Following these topics At the end of the hook are three apare three chapters dealing with the topics pendices dealing with nomenclature, the of resct,ion mechanisms in generd, acids literature of organic chemistry, and a list and bases, and t.he effect, of st,meture on of preparative reactions, compiled on the reactivity, respectively. hasis of functional groups. These reacPart, Two deals with the reactions of tions are also numbered so that the pertinent discussions in the previous chapters organic compounds arranged by reaction type rather than by ftmctional groups. ere easily accessible. This approach is fairly standard in adA special feature of this hook is the vanced texts. There are t,en chapters in extensive Meratme documentation of the all dealing with electrophilic, n~~cleophilie, material. At this stage of the student's and free radical suhst,itntians in aromatic career he should be emphatically and and aliphatic systems, addit,ions to carhonconstantly urged to consnlt the original carbon and carbon-hetero multiple bonds, literature. Professor March is to be
Jerry March, Adelphi University. McGraw-Hill Book Company, New York, 1098 pp. Figs. and 1968. xiv tables. 16 X 23.5 cm. $16.75.
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-Reviewed
in this Issue
Jerry Maveh, Advanced Orgg-nnic Chemistry: Readions, Mechanisms, and Stntct,ure . . 537 . . ,537 Afekd~.umR. Winslead, Organic Chemistry Strt~ct,walPmblems William H.Guenther, Qunntitalive Chemistry: Measurements and Equilibrium . . ,538 Alfred 11. Garrett, W . T . Lippincotl, and Frank Henry Verhoek, C h o m i s t , ~ : . . ,538 A Study of Matter H . A. 0.Hill and P . Day, editors, Physical Methods in Advanced Inorganic . . ,538 Chemistry E. A. V . Ebsuorlh, A . G . Maddock, and A . G . Sha~pe,editors, . . . A549 New Pathways in Inorganic Chemistry . . . A.550 George J . J a m , Molten Salts Handbook Richard J. Higgins, Experimental Electronics, An Introductory Laboratory . . . A550 Manual for Physical scientist,^ A m i n H e m a n n , Die Begriindmrg der Elektmchemie und Entdekung der IJltravioletten St,rahlen von Johann Wilhelm Ritter. Eine Auswahl aus . . . A551 den Schrifteu des romantischen Physiker . . .A.5.51 Dennis Flanagin, editor, Materials, A Scientific American Book
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commended for making this readily possible through inclnsion of well over three thousand references. The literature is well covered through 1066 with a sprinkling of papers in 1067. Included in t,his number is practically every pertinent review article published since 1950. Also each discussion of s, specific reaction in Part Two closes with a listing of all "Organic Syntheses" procedures which are illustrative of the reaction. The covemge here is through Volume 46. Thus for the student, or for that matter the research worker using this work for reference, the steps between the textbook and the laboratory are shortened. Errors of s. typographical nature are infrequent. Of the more than fifty random references checked only one (reference 283, p. 633) was found to be slightly incorrect. On page ,502 the sub-heading C should read "Nitrogen Nucleophiles" instead of "Electrophiles." One might also argue with the author's use of the Russian spelling "Zaitsev" instead of the familiar "Saytseff." This hook attempts to cover a great deal of organic chemistry a t an advanced level. I t is my opinion that from the standpoints of orga&ation, content, and style of writing the job has been done well. The book is an uo-to-date textbook which will give the stuient a broad coverage of the field. I t will also continue to be useful later a s a secondary source or as s. place to find references to primary sowces on a particular topic. This book can also be recommended to the organic chemist who needs a refresher with respect to the ideas and literature of the mid-sixties.
JOHN C. COCHRAN Colgatc Unwersity Hamilton, Ncu, York 13346
Organic Chemistry Structural Problems
MeUrum D. Winstearl, Bucknell University. Sadtler 1Ieseal.ch Labot.atmies, h e . , Philadelphia, 1968. 230 pp. Figs. and table-. 21.5 X 28 em. 84.95, spiral hound. The unique feature of this pmhlem hook is that the 110 problems contain chemical and physical information ahortt the unknowns in addition to spectral dat,s. The student thus h m the type of data which the practicing organic chemist has as he attempts to solve structural problems. I n many problems t h e x is swplus informat,ion which can, however, he nsed as confirmatory evidence. Very few ultraviolet spectra are given. For the majority of pl.oblems tho infrared and/or nmr spectra of the eompounds involved are displayed. The spectra are particolarly clear. No actual or block-type maax poctrs. are displayed. A nmlber of problems do contain m.lc ratios for prominent peaks. The emphasis is then on utilizing the infrared and nmr spectra plus the chemical and physical data to &?signstructures. Answers to selected problems are given a t the end of the hook. The instructor eau obtain a complete answer section. The reviewer gave a. few selected prohlems to senior students in a qualitative organic
Volume 46, Number 8, August 1969
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chemist~.yclass. The students found them chnllengit~gbut answerable. The modest cost makes this hook II very good investmeut for both the teacher and his students. L d b u W. HIYNI?S The College qf Woosler IVooster, Ohio 446#1
Quantitative Chemistry: Measurements and Equilibrium
William B. Guenlher, The University of t,he Sooth, Sowsnee, Tennessee. Addison-Wesley Publishing Company, Inc., Reading, Massachusetts, 1968. xv 400 pp. Figs. and tables. 17 X 24 em. $9.75
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This new textbook, falling generally in the area of snslyt~icalchemistry, emphasizes chemical equilibria and the physical chemistry of sohtions. In the preface, tho aothor states: "Because of the wide variety present in evolving college chemistry programs, this text is an ntt,empt to steer a middle path between repeating too much of the material covered in the general or element,avy physical ehemist,ry eonmes and assuming more fluency in chemical theory than. sophomores and juniors are likely to have." The attempt is qnite snccessfol, and the sut,hor and prtblisher should be congrattdxted on the quality of the hook and its freedom from significant errors. The text might even he (he baais for an interesting course for nn honors group of second-semester freshmen, after a semester of atomic and molen~lms t n ~ c t ~ n e . One finds the fnndamental proredwer of clnssicnl qmntitative xndyris (tilt.%tion methods, gravimet~.y,solvenl. extrnction, ion exchange) treated in R very cnndensed fashion, htlt. from a fresh viewpoint, wing modern rhemical example?. Inorganic systems mceive more emphasis than orpanic ones. The lahorntory wovk, wing B somewha(. opewended pmjecl. appmnrh, pa~allels the lerture material whidl emphasizes the ways in which rhemist.; w e quanlitntive mensnremenis lo determine equilihl.i,~mconstauts. The nothor has given much attention to the grxphiral inleqwetation of data, for equilihriwn systems (leaning heavily on a nnmher of standard works, in particolas the monograph by J. N. Butler). I n this effort he has succeeded admirably. Both Job's method and Bje~nun'smethod arc illustrated, and n nnmber of experiments yield data on the eRect of iouic strenglh on I
