JOURNAL O F CHEMICAL EDUCATION 0
ADVANCED ORGANIC CHEMISTRY
E. Earl Royals, Associate Profeuor of Chemistry, Emory Uni948 pp. versity. Prentice-Hall. Inc., New York. 1954. xii 23.5 X 15.5 cm.
$10.
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INRECENT yearn second C O U T P ~ Sin organic chemistry, whether on the undergraduate or beginning graduate level, have commonly become courses on electronic theory and organic reaction mechanisms. This trend is of recent enough origin t h a t relatively few suitable texts are a t present available, in unhappy contrast to the plethora of those on the elementary orgmie level. The appearance of a book as comprehensive and as lucidly, often vividly, written as the present "Advanced Organic Chemistry" is thus a welcome event. I n 846 pages of actual text Dr. Royals has presented a. wealth of factual material interwoven with unifying theory. He has pointed out that in addition t o its use as a textbook the book "is intended [to be] useful to graduate students throughout their graduate training, [and that] it is also hoped that practicing organic chemists desirous of maintaining contact with the broad field of organic chemistry and the more modern development therein will find it useful." Although tbe claim on the dust cover that "no experimental fact is quoted without complete documentation" is somewhat exaggerated, the hook is generously documented with mare than 1500 literaiure references, approximately 35 of which carry the literature t o 1950-51. The author index and thorough subject index oomprise a total of 102 pages. In the first chapter, entitled The Structure and Reactivity of Organic Compounds, the author presents the fundamentals of electronic theory as applied t o the resting and reacting molecule and general principles of chemical kinetics and equilibrium which are t o be used throughout the litter discussions. Eleetronic theory is presented as an "aid t o the understanding and memory, not as a predictive tool." This first chapter is a composite of material t o be found in Pauling's "Nature of the Chemical Bond," Wheland's "Theory of Resonance," Remiek's "Electronic Interpretations of Organic Chomistry," Ingold's Chemical Review article (and recent book, although the latter appeared too late t o be used directly), Hammett's "Physical Organic Chemistry," and Eyring's treatments of rate prooesses. I t represents n d l organized and pedagogically useful survey of current ideas and lays the groundwork for the blending of facts and theory throughout the remaining chapters. In lagiod asequenee the author then develops in successive chttpters the chemistry of the alkanes, the cyelodkanes, the nlkene linkage, aromatic hydrocarbons, and the alkynes, and finally ~ l w o r ~foul v c1upwr.s t o rurhwlyl rompound.; AIxking uzr ui thr iollouing g r w r d whvrnr: (lirst) methods of zvntlwi~i, snd of tlw hsdrocor1,on; (wrond) r h t m ~ c ~~ lI I H Y IIll(. O ~rhcmi-trv , and their most important univalent derivatives is sy&naticall,y evolved. For example, the chapter on the alkene linkage begins with a survey of aliphatic halides leading into studies of the mechanisms of aliphatic suhstit,ution and elimination reactions in general and then logically merging into tho wnthesos of tho nlkenes through elimination reactions. The disoussian of ohemiml behavior fallows this pattern: isomerisation, free radical and polar polymerizations, oxidations, addition of halogen (the discussion of the mechanism of vhich allows a smooth transition to n general discussion of neighboring group participation in displacement reactions), and this is followed by additions of unsymmetrical reagents to the alkene linkage, and so on. In the four chapters on carbonyl compounds all classes of carbonyl compounds-aldehydes, ketones, acids, esters, amides, et~.-are considered concurrently. The material is introduced with a consideration of the nature of the carbonyl group, and the remaining three chapters are devoted, respectively, t o methods of preparation of carbonyl compounds, addition reactions of the mrbonyl group, and reactions dependent upon active hydrogen. There are n, surprising number of typographical errors in formulas, which may he distuvhing to studentp. Although the au-
thor has made a serious attempt t o document adequately throughout, he h t ~ soccasionally been neglectful, ss for instance in hip discussion of dehydrations of the T~ehugaevtype, where he presents without acknowledgment a cyclic mechanism like that proposed in 1938 by Hurd and Blunok, in 1940 by Hiiekel, Tappe, and Legutke, and in 1941 by Stevens and Richmond and discussed in Alexander's "Ionic Reaction Mechenisms." I t is no fault of the author if s book with the broad coverage of the present one is in places incomplete by the time it reaches the publication stage. Foreseeing thia inevitability, he has indicated that he "endeavored to so present meehaniatio considerations that future research will require that what is here given be extended and elaborated rather than discarded." Nevertheless, same readers may feel that the book hassufferodfmm the omission of pertinent eantributions and concepts available s t what appeas8 to be the "eut-off" date (1950-51). The reviewer would cite contributions to the field of aromatic suhstitutiom-particnlarly those by the English school-application8 of molecular orbital theory to organic chemistry, and recent contributions to the stereoohemistry of ring compounds and t o the field of nucleophilic substitution reactions as perhaps outrtanding omissions of this type. However, no one textbook could ever satisfy d l readers, and Dr. Royals has skillfully developed here B stimulating picture of basic organic chemistry, neither sacrifioing factual material nor neglecting theory, as so often is the case in comprehensive treatments of fact. The hook is a rich wurce of d e scriptive material set in a framework of mechsnktic rstionalizstion. FR.4NCES BERLINER
Comeoa BBYNM ~ w n BRYNMAWR. PENNSTLVAXIA
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FENTON'S NOTES ON QUALITATIVE ANALYSIS
B. C. Sounders, Fellow and Charles Kingsley Lecturer in Natural Sciences, Magdalene College, Camhridge University, England. Revised edition. Cambridge University Press, New York, 1953. 124 pp. 9 figs. Many tables. 19.5 X 25.5 om. $2.75. As INDICATED by the title, this book presents a summary of qualitative analysis (practical). The form and content of the hook is reminiscent of a lecturer's set of notes used in outlining the essential chemistry to he considered in 3 thorough laboratory course in qualitative ttnalylysis. Part I summarizes the principal reactions of common cations and anions. Part I1 presents outlines of analytical prooedure including both dry and wet tests. Analysis in the dry way includes observation of the color of salts, closed tube ignitions, blowpipe operations, flame tests, and bead tests. Analysis in the wet way is presented in the classical manner based on a chloride group, acidic sulfide group, hydroxide (NH40H NH,CI) group, basic sulfide group, and a. carbonate group separation of cations. Magnesium is separated as the phosphate and standard tests are used to identify the soluble group. Various classification tests arc presented for acid mdicals and for gases. A number of alternate procedures are suggested and discussions of the fundamental reactions are included. Part 111 is a. "modernization" of qualitative techniques. Some semimicro methods are outlined and spot test and chromatographic techniques are discussed briefly. The book is remarkably free from errors and is well printed and hound. The oresentatition would seem to make the book best
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tive chemistry. PHILIP W. WEST LOUISI*N* STATEU N ~ V E R B ~ T I B*TON ROUC.. L o v , ~ , * ' ~ *
