A. F. Holleman's Organic Chemistry

A. F. HOLLEMAN'S ORGANIC CHEMISTRY. J. P. Wibaut, Professor of Organic Chemistry, University of. Amsterdam. Translated from the sixteenth Dutch editio...
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JANUARY, 1953

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electric circuit there are two irreversible processes, thermal oonduetian and Joulean heating, so interconnected that any device that approaches one to reversibility necessarily drives the other far into irreversibility. Kelvin tackled this problem bymeansof what be realized was an "illegal operation." Bridgman mriously considers this problem in the third lecture. He utilizes experimental results on single metal crystals which were not available to Kelvin, and with the aid of these and of several new concepts iram the domain of paper-and-pencil operations, restores legitimacy to the situation. I n suite of the aereement between the verbal and instrumental proportion to its physical siee. ANTHONY STANDEN T H EIVTERBCIENCE ENC~~OLOPEDIA BROOBLTN. NEWYOIB

A. F. HOLLEMAN'S ORGANIC CHEMISTRY

J. P. Wibaut, Professor of Organic Chemistry, University of Amsterdam. Translated from the sixteenth Dutch edition by S. Coffey, 1.C.I. Dyestuffs Division, Manohester. Elsevier Publishing Co., Ino., Houston, Texas, 1951. xvi 622 pp. 6 6 figs. 51 tables. 18 X 26 cm. $9.

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HOLLEMAN'S original "Organic Chemistry" hrte been through fifteen previous Dutch editions and was last translated into English in 1930. The present edition was undertaken by Prof. Wibaut "with special care being taken that the original character of the book should be retained," i. e., the subject matter should he treated from both a structural and physioochemical viewpoint. The book is intended for students of chemistry, biology, and medicine, and is divided into sections on general aspects, aliphatic, polyfunctianal aliphatic, aromatic, alieyclic, and heterocyclic com~ounds. The text attempts ta provide a broad elementary background in the science as well as a survey of more recent developments of theoretical or practical importance. Toward a fulfillment of the latter objective line print paragraphs are frequently inserted into the main textual material, and throughoot the book specifio material of more recent origin and advanced nature is to he found in such sections. Wherever appropriate there is included a brief discussion of the classical chemical evidence upon which accepted structural formulas are based, including data from both degradstive and synthetic sources. Names of original investigators are widely given and the book includes a six-page author index. Unfortunately, the dates of investigations are not generally included, however, and the text is of little value as a guide to the original literature. Criticisms of the text fall into both general and specific categories. Generally speaking, it appears to this reviewer that the book attempts perhaps too much for one of its siee. The dividing line between elementary and advanced material seems rather more abrupt than desirable for the beginning student. Thus, for example, the more advanced matter in the fine-print sections mentioned previously is not always obviously related to the more elementary material precedina it, suggestina the possibility of confusion for the u&ophistic&d reader. serious, perhaps, is the author's rather fragmented approach to the subiect. eeneral relationshius amone or. The underlvine . .. .. gmir rcxctiona n w h> 1.0 inr,$nrcle~rlydrlineated f n m the viewp i n t r oi inr .lln~.i.mor an3lr,o\, nn.1 rlw rc.trlrr i h lei, s i ~ hlittle of nwrr rerenr unif\,i,rg trend.; in t 1 ~ vsvimec. Thr ,~ppreeiatio~t nonunified approach has the further result of considers.hle unnecessary repetition in some sections, and the freshness and s~ontaneitvof the translation suffer occasionally therehy. The author's treatment of his material neems in general a little noncriticel; yields, side reactions, and in particular limitations of organic reactions, seldom receive consideration. Discussions frequently contain undelined or poorly defined terms, introducing a further source of confusion to the beginner. Mare specific critiesims vary in importance and are indeed too

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numerous to tabulate in detail. Suggestions in the preface to the oontrrtrv notwithstandine. there is verv little adeauate treab

thermachemistry and molecular refraction receive treatment the detail of which seems out of proportion for a general text, while others such as spectrographio and kinet,ic techniques receive too superficial a treatment. Many importsnt topics receive what this reviewer feels to be somewhat insdequste eonsideeration on either the descriptive or theoretical sides. dmocg such topics are spectra and constitution, org~nometallic compounds, free radiesls, moleoular rearrangements, structure and reactivity, optical and geometrical isomerism, polyme~ization,certain natural producbs, and industrial or technological considerations. To be sure, discussion of such subjects is not totally a h s e ~ ~but t, treatment seemsinadequate as a result of either excessive brevity, dilution with extraneous material, or lack of correlation among widely distributed examples. Organic nomenclature receives s distinctly superficial treatment, no attempt being made to develop a systematic approach to the subject. This fact, combined with an absence of illustrative problems, further insures the text's inadequacy for a beginning student. Such mechanistic material as has been included is frequently outdated and presented noncritically with only limited emphasis on supporting experimental data. The concepts behind and applications of resonance theory are handled with an undesirable brevity. While the numher of factual errors in the book amears low.

many places economy as well as generdity would have been

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conditions over the arrow. Oeeasio&J analog& are drawn from inorganic chemistry that are erroneous in the light of current theory. Perhaps because of the fragmented approach to the material, the subject index is far from adequate. There are, for example, only two entries each under mesomerism and oxidation, one entry each under alkylation and nitration, and no entries under halogenation, reduct,ion, sulfanation, acidity, or molecular rearrangements. Printed on heavy paper and neighing over four pounds the hook is cumbersome and uncomfortable to read. Attempting a t once to he both elementary and advanced, it is perhaps surprising that a book of this size can be as adequate as the present is. The inadequacies resulting almost inevitably in an attempt of the present sort, however, make it difficult to recommend the book either for the beginning or more advanced student of organic chemistry. WILLIAM A. BONNER

GTANPORD UNIVERSITY ST*NBORD.C*,,,PORNI*

HANDBOOK OF DANGEROUS MATERIALS

N. Irving Sox, Toxicologist, General Eledrio Co. Assisted by

M.J. O'Herin, Fungicide Laboratory, General Electric Co., and W. W. Schultz, General Engineering Laboratory, General Electric Co. Reinhold Publishing Corp., New York, 1951. vii 848 pp. Illustrated. 18.5 X 26 em. $15.

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Tnrs book is divided into the following sections: (1) General Chemicals: Under this heading there is a listing of 5000 dangerous materials, together with information reaardina hazardous properties, treatment, antidotes, extinguishers, &orage and handling, personnel safety precautions, physical properties (flash point, autoignition point, etc.), shipping regulations and labeling instructions. (2) Explosives: Surface storage of explosives, destruction of explosives, chemiosl ammunition and miscellaneous explosives, high explosives and low explosives.