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VOLUME 33, NO. 11, NOVEMBER, 1956 apparent limitation in the preparation of the monograph. Later volumes will no doubt supplement and modify the essentially sound framework presented here. RALPH A. OLGEN rnoa~~un*~ MONTANA STAT=C O L L ~A~o E &*TION EXPERIMENT B O ~ E M AMONT*N* N.
ORGANIC CWEMISTRY
Louis F. Fieser and Mary Fieser, Harvard University. Third edition. Reinhold Publishing Corp., New York, 1956. v 1112 pp. 16 X 23.5 cm. $10. Textbook edition available from D. C. Heath and Co., Boston.
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THEthird edition of this distinguished textbook has been thoroughly revised in recognition of the great advances in organic chemistry, both theoretical and experimental, whieh have occurred since the publishing of the second edition in 1949. This period, from 1950-1956, has witnessed the elucidation of structure and total synthesis of many natural products. It has seen the use of isotopic tracers and microbiological techniques greatly aocelerctte the determination of pathways of hiogenesis. Theoretical concepts such as the orbital theory and eonformationsl analysis have been of great service. Greater understanding of the mechanisms of organic reactions has been achieved. These and other developments which make this era such a rich period are incorporated in the revised third edition of this textbook. This book contains 40 chapters, two less than the second edition. Changes include removal of the chapter on microbiological processes, and combination of the chapters on rubber, fibers, and plastics (66 pages) into a 33-page chapter on polymers. A chapter on alkaloids (21 pages) has replaced the ll-page section in heteror.ydes devoted to alkaloids in the second edition. The total number of text material (1039 pages) is 38 pages less than the second edition. The format and order of arraneement is essentiallv l l i l l l t 1 1 0 P h i l 111" ~ 11. tl#emmc, ~ l t h o l l ~TI., ' ~ h a n ~>31metl w :,I making 11.e Ixmk n w w useful as a.student text." As with the second edition, Chapten 1-4, 611, 1416, and 20-33 (approximately 700 pages) would constitute s. gaod introductory course. These chapters of basic organic chemistry have undergone the least modification, and their organiaation is very similar to that of the second edition. Probleme are given a t the end of ohapters, and answers to these problems are included a t the end of the book. The table of contents has not been outlined in detail as in the second edition. This is one change with which the revisuer does not agree. The useful three-page appendix, giving bond distances and ener-
gies, resonance energies and solubility data for a number of compounds, as well as electronegativity values for several elements, has been maintained. I n line with the trend of placing greater emphasis on the theoretical aspects of organic chemistry, these concepts are introduced early and used throughout the book. Resonance and the orbital theory are introduced in Chapter 3 on the alkenes. These concepts are further emphasized in the chapter on benzene. Conform* tional analysis is introduced in Chapter 12 on ring formation and stability and finds much use in the chapter on steroids. Rearrangements are introduced (the Wagner-Meerwein rearrangement) in Chapter 6 on alcohols. The use of the electronic theories is illustrated in Chapter 5 where the distinction is made between the electrophilie and nucleophilic additions to acetylene. The mechanisms of suhstitution are introduced in Chapter 7 on alkyl halides. These mechanisms are further "resented in the chanter on reaction
inadequate. Some desirable minor additions have been made. The chapter on alcohols includes a brief discussion of mercaptans and sulfides. The chaoter on stereoisomerism includes diphenyl isomerism under geometrical isomerism. The seetion on enoh and unolates has been moved from ring formation to aldehydes and ketones and expanded. A major addi. tion is a section on tropalones under phenols. However, the most striking changes occur, as expected, in the chapters on natural products. The inclusion of tropolones and the expanion to chapter st&tus of alkaloids has been mentioned. Tho
duvigneaud, and Lippmann among others, is especially significant. The chapters on steroids, imprenoids, and vitamins have been completely revised and the chapters an heterocycles and dyes slightly expanded. The removal of the chapter on microbiological processes caused the deletion of the material on ' bacterial fermentation, which the reviewer regrets, in view of the importance of microbiologicel synthesis, e.g., cortisone. The chapter on chemotherapy is interesting and valuable, although some workers in the field might have desired the inclusion of functional drugs. .A new feature is the introduction of biographical sketches of 454 chemists. These sketches give the chemist's full name, vital statistics, the university a t which a higher degree was obtained or where study was pursued, the professor under whom he worked, and the university or company of his major service. With the exception of certain errors in birth-
dates and the inevitable disagreement with some of the choices, this section is highly commendable and useful. This book will certainly he a. vduluable addition to our literature. Beautifully bound in a red and gold cover, nicely printed, and written with the clarity characteristic of the Fiesers, i t will take its rightful place ss an outstanding testhook in the English language. 8.4MUEL P. MAEEIE Fma U ~ l v s n s l ~ r N*BHVILLE. TENNEBBEE
THE CHEMISTRY OF PHENOLIC RESINS
R.W.Martin, ShellDevelopmentCompany. John Wiley & Sans, Inc., New Yak, 1956. xi 298 pp. Figs. and tables. 15.5 X 23.5 cm. $9.50.
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THE first completely synthetic high polymers to find extensive commercial utilization were prepared from phenolformaldehyde condensation products as a. result of the pioneering work of Baekeland almost 50 years ago. Since that time these and related polymers from other phenols, ddehydes, and ketones have assumed an increasingly important industrial role. This well-organized treatise brings together in a relatively small volume practically all of the important work whieh has hem done on the ohemistrv of the hiehlv
lure, the large number of references cited will he most useful to those who wish to pursue further some particular phase of the subject. I n certain instances the author has attempted a, critical analysis of eonfliet,ine results found in the literature. Brief summaries of current mrtnufacturing procedures and end uses for the praducts are given. I t may seem somewhat surprising that such a large portion of the book is CMcerned ~rimarily with well-defined, low moleculm weight substances. Actually this material is essential for an understrtnding of the structure of phenol-formaldehyde polymers and the reactions leading to their fomztion. Extensive tables listing melting points and references t o individual hydroxymethyphenols and his(hydroxyphenyl>methanes are given. Such information along with that in the c h a p ters on heterocyclic compounds and reactions of phenol-aldehyde eondonsation products will be of interest to organic chemists in general. A gaod treatment of the recent work which has resulted in significant advances in rate studies an phenolformaldehyde condensations is given in Chapter X on Reaction Kinetics. While the nomenclature emplal-ed for certain of
