book
reviews Editor: W. F. KIEFFER College of Wooster Wooster, Ohio
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
Jerry March, Adelphi University. McGraw-IIill Book Company, New York, xiv -f 1098 pp. Figs, and 1968.
J. Chem. Educ. 1969.46:537. Downloaded from pubs.acs.org by 5.189.202.213 on 01/28/19. For personal use only.
tables. 16 X 23.5
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$16.75.
Professor March has written a text aimed at the second course in organic chemistry at the undergraduate level and/or the survey course in organic chemistry at the graduate level. In the text he covers three major areas; the structure of organic compounds, the reactions of these compounds, and the mechanisms by which the reactions take place. The book is divided into two parts. The first six chapters of Part One deal primarily with aspects of the structure of Included in this organic compounds. section are the topics of bonding (localized, delocalized, and weaker interactions), stereochemistry (optical isomerism, geometrical isomerism, conformational analysis, and the consequences of ring strains), reaction intermediates (carbonium ions, carbanions, free radicals, and carbenes), and instrumental methods for determining structures. Following these topics are three chapters dealing with the topics of reaction mechanisms in general, acids and bases, and the effect of structure on reactivity, respectively. Part Two deals with the reactions of organic compounds arranged by reaction type rather than by functional groups. This approach is fairly standard in advanced texts. There are ten chapters in all dealing with electrophilic, nucleophilic, and free radical substitutions in aromatic and aliphatic systems, additions to carboncarbon and carbon-hetero multiple bonds,
eliminations, rearrangements, and oxidation-reduction reactions. Each chapter begins with a discussion of the mechanism or mechanisms proposed for that type of reaction, followed by a discussion of orientation and reactivity in terms of the usual parameters; substrate, solvent, etc. Then a large number of examples of each reaction type are discussed. The sequence of reactions follows a logical pattern wherever possible and each reaction is given a code number for cross reference. For example in Chapter 15, Addition to Carbon-Carbon Multiple Bonds, reactions in which hydrogen adds to one side of the double bond is a main heading. In subheadings are the reactions in which halogens, oxygen, sulfur, nitrogen, hydrogen, boron, and carbon add to the other side of the double bond. The second main heading includes reactions in which hydrogen does not constitute one of adding moieties. Reactions in whicli halogens, oxygen, nitrogen, and carbon add to one or both sides make up the sub-headings. Thus this chapter includes such diverse topics as electrophilic addition reactions, catalytic hydrogenation, the Michael Reaction, and the Diels-Alder Reaction. At. the end of the book are three appendices dealing with nomenclature, the literature of organic chemistry, and a list of preparative reactions, compiled on the basis of functional groups. These reactions are also numbered so that the pertinent discussions in the previous chapters are easily accessible. A special feature of this book is the extensive literature documentation of the material. At this stage of the student’s he should be emphatically and career constantly urged to consult the original literature. Professor March is to be
—Reviewed in this IssueJerry March, Advanced Organic Chemistry: Reactions, Mechanisms, and 537 Structure .537 Meldrum B. Winstead, Organic Chemistry Structural Problems William B. Guenther, Quantitative Chemistry: Measurements and ...538 Equilibrium Alfred B, Garrett, W. T. Lippinrott, and Frank Henry Verhoek, Chemistry: 538 A Study of Matter H, A. O. Hill and P. Day, editors, Physical Methods in Advanced Inorganic ...538 Chemistry E, A. V. Ebsworth, A. G. Maddock, and .4. G. Sharpe, editors, A549 New Pathways in Inorganic Chemistry A550 George J. Jam, Molten Salts Handbook Richard J. Higgins, Experimental Electronics, An Introductory Laboratory -A550 Manual for Physical Scientists A nnin Hermann, Die Begriindung der Elekl rochemie und Entdekung der Ultravioletten Strahlen von Johann Wilhelm Ritter. Eine Auswahl aus A551 den Sehriften des romantischen Physiker A551 Dennis Flanagin, editor, Materials, A Scientific American Book ...
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commended for making this readily possible through inclusion of well over three thousand references. The literature is well covered through 1966 with a sprinkling of papers in 1967. Included in this number is practically every pertinent review article published since 1950. Also each discussion of a specific reaction in Part Two closes with a listing of all “Organic Syntheses” procedures which are illustrative of the reaction. The coverage 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 a 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 “Saytzeff.” This book attempts to cover a great deal of organic chemistry at an advanced level. It is my opinion that from the standpoints of organization, content, and style of writing the job has been done well. The book is an up-to-date textbook which will give the student a broad coverage of the field. It will also continue to be useful later as a secondary source or as a place to find references to primary sources 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 Colgate University Hamilton, New York 13346
Organic Chemistry Structural Problems Meldrum B, Winstead, Bucknell University. Sadtler Research Laboratories, Inc., Philadelphia, 1968. 250 pp. Figs, and tables. 21.5 X 28 cm. $4.95, bound. spiral The unique feature of this problem book is that the 110 problems contain chemical and physical information about (he unknowns in addition lo spectral data. The student thus has (he type of data which the practicing organic chemist lias as he attempts to solve structural problems. In many problems there is surplus information which can, however, be used as con-
firmatory evidence. Very few ultraviolet spectra are given. For the majority of problems the infrared and/or nmr spectra of the comThe pounds involved are displayed. spectra are particularly clear. No actual or block-type mass spectra are displayed. A number of problems do contain mje ratios for prominent peaks. The emphasis is then on utilizing the infrared and nmr spectra plus the chemical and physical data to assign structures. Answers to selected problems are given at the end of the book. The instructor can obtain a complete answer section. The reviewer gave a few selected problems to senior students in a qualitative organic
Volume 46, Number 8, August 1969
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