RECENT BnOKS ELECTR~NIC INTERPRETATIONS OX ORGANIC CBEMISTRY. A. E. Remick. Assistant Professor of Chemistry, Wayne University. John Wiley & Sons. Inc., New York, 1943. v 474 pp. 19 figs. 77 tables. 13.5 X 21 cm. $4.50. The title of thij book is scarcely a n accurate description of its scope nnd content. A few sentences lifted from thr nuthor'iprcface may be more informative. " . A rati5factory preparative pruccdwe demands: (1) that the proposed reaction be thcrmdynamically powihlc. (2) that the renction tdsc dace with asullicitntl~hkh vdocitv to be ~ r a c t i cable, and ( 3 j that there be as few sidereactions possib;le and that those which are inevitable take lace much mare slowlv than ~, thc mnin reaction. It sholnld be a t once apparent that if we would predict these things we mu\t first undersrmd the effccts of atructurd and environmental changes on both the free energies and activation energies of organic reactions. This seems to be a demand for a fusion of electronic theories of organic chemistry with such modem developments in physical chemistry as the quantummechanical concept of resonance and the transition-state theory of reaction rates. The main purpose of this hook is to show how this fusion of ideas has been satisfactorily achieved. I t is intended that this book shall serve the dual purpose of a review and an advanced textbook.. . ." In your reviewer's opinion the author has made, on the whole, an intelligent choice of subject matter, when judged on the basis of the objectives announced. Some readers may feel, with the reviewer, that a disproportionate amount of space has been expended on the rather nebulous physical concepts, esoteric terminology, and tortuous interpretations of the English school-now chiefly of historical interest to American organic chemists, a t least. This, however, is perhaps a matter of personal taste and opinion. Within the areas selected for treatment the coverage of significant literature has been reasonably thorough, although there are a few rather surprising omissions, such, for instance, as the neglect of Anderson's study [I. Ckem. Soc., 57, 1673 (1935)], indicating that the basis of the conductivity of hexaphenylethane in polar solvents like liquid sulfur dioxide is ionization in the sense (C.H&C 5 (CsHs)sC+ s, rather than in the sense (CsH&C: C(CsHs)~ (C6H5)&!+ 4- (CsHs)C-, as Gomberg had earlier supposed (p. 46). The text is considerably better mitten than the average, and the exposition is exceptionally lucid, being marred chiefly by occasional lapses into oversimplification or by condensation to the point of mild misrepresentation. Cf., e. g., the beginning sentence of the first new paragraph onp. 140: "Thereisconsiderable evidence from the field of quantum mechanics which shows that the energy of a bond between two given atoms is not much affected by other atoms in the molecule." I n the field of critical evaluation and independent interpretation and synthesis the author lays himself open to criticism only for the modesty with which he consistently refrains from attempting anything of the sort. In the admittedly difficult task of arrangement and organization of subject matter the author has permitted his projected outline to result in some rather gruesome dismemberments of topics that, in thereviewer's opinion, should have been highly integrated a t all costs. By way of example, a section entitled "Bond Energies" occupies the greater part of pages 1 3 M 3 in Chapter VI ("Some Contributions from the Field of Chemical Physics." pp. 133-87). The opening discussion would lead the student to believe that "bond energies" may be expressed in terms of AH values. T w Little emphasis is laid on the fact that Pauling's socalled "bond-energy values," reproduced on page 141, include kittens of such radically different breeds as H-H and 1-1 on the one hand and C-H and C-C on the other. The former may be expressed in terms approximating pure potential energy values;
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for the latter this was not even attempted. On page 142 Kistiakowsky's data on the heats of hydrogenation and bromination are cited as indicating that there may, after all, he something a trifle smelly about t h e postulate of "constant hond-energy values," although nothing is said of the even more cogent argument to this effect supplied by Rossini's heats of combustion and derived energies of formation for hydrocarbons. The subject of bond energies craps up again, pages 290300, in Chapter I X ("Electron-Pairing Reactions," pp. 259-310). On page 295 Baughan's very proper criticism of Pauling's adopted value for the vaporization of carbon, and the effect of more probable values of this quantity an Pauling's C-H and C-C "boud-energy" values are mentioned. On page 297, in a footnote, the student is reminded of the distinction between AH and AF, and the practice of using AH values to implement AF arguments is criticized. At length, on page 300 some physicochemical evidence to the effect that primary, secondary, and tertiary C-H bonds differ appreciably in strength is adduced, but spectroscopic evidence (cf. Brackett, Barchewitz) and quantum-mechanical calculations (cf. Eyring) leading to the same conclusion are ignored. Nowhere isit pointed out that arelatively small difference in the values ascribed to methane and primary C-H bond energies would lead to the necessity for a relatively large upward revision in the value ascribed to an ethane C-C bond on the assumption that all C-H bonds are equivalent. The appendices ("I,An Elementary Exposition of the Theory of Atomic and Molecular Structure," pp 42333; 'TI, Refractivity and Chemical Constitution," pp. 43444; "111, Dipole Moments," pp. 445-8; "IV, Background for the Study of Nonaqueous Solutions," pp. 449-60; "V. Table of Basic Principles," pp. 4614; T I , Table of Symbols," pp. 4 6 M ) should prove useful, especially t o the student handicapped by limited physicochemical training. Your reviewer now fears that in the attempt t o document his criticisms specifically he may have transmitted a less favorable impression than he, himself, holds of the volume under consideration. Frankly, your reviewer is your reviewer's favorite author, and he can find so much to criticize in his own work that he never gets around to offeringit for publication. OTTO R E r m n U N N B R ~ I T YOB CHICAGO
ILLINOIS CEUCAOO.
BI~CHEMISTRY FOR MEDICAL STUDENTS.William Veale Thorpe, Reader in Chemical Physiology, University of Birmingham (England). Third Edition. The Williams & Wilkins Company. Baltimore, 1943. viii 476 pp. 39 figs. 14.5 X 21 cm. $4.50. Restrictions in the use of paper are said to have governed the size of this little book, but they have not "cramped its style" or usefulness, for here we have a beautifully compressed, fairly brief, fully modern presentation of the subject of normal human biochemistry. The preface to the volume gives a lucid and honest evaluation of it. "The aim of this book is to present an account of the biochemical Drocesses known to occur in the healthv human h d y ~.upl,lrnlentin):ntin rcrorntnrndcd tat-books of Phyiiology)." In thi. third rclicion "a ron&leral~lrnrnoont uf new material has, hmvwer. bccn irlcorporaterl by rrarrangnnmt of the text. In response to frequent requests a short chapter on the Chemistry of Respiration has been added." The author has "tried to provide what the medical or dental student may want to know and to omit that which he is never likely to require." A few of the features found helpful here are the thorough treatment of physicochemical principles involved in the behavior of water in tissues, the large and clear structural formulas, the use of
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varied type fonts for emphasis and organization, photographs of absorption spectra of hemoglobin and derivatives, and the cogent treatment of such topics as purine metabolism. The chapters on food and nutrition are significant because of theway in which they present the subject from the viewpoint of the inhabitants of the British Isles. The problems of supply, cost, and rationing are excellently set forth, from the standpoint of economics as well as protective nutrition. A brief appendix summarizes data on blwd, urine, and nutrition, and presents a rather complete "Conversion Table for Weights and Measures." Of the 95 publications listed in the bibliography the majority are, of course, of British origin, so that ~f r h l j text wrrr tlw t.xrlusive selection for a rlasi i n our country, a wpplm~mtaryam1 parallel lirt of Antrrican literature would be hrll>ful. Aside from thc prcsenmtion on page X l l of dctoxicated be&ic acid in glucosidi&nion with glucur&ic acid instead of.as its ester, no errors have been detected. The newer id- of intermediary metabolism are hospitably included as possibilities with a typically English gallantry. The effects of the war in slowing the interchange of professional publications are shown in minor instances where the book is not strictly up to its dating, from the viewpoint of American research. The use of diphthongs in such words as "haemin" and "oestrone," and consistent "labour" and "honour," rather than confuse the reader, give him a "flavour" with his chemistry, and a diversion from his often flat American dialect. DAVIDLYMAN DAV~SON
LABORATORY MANUALOF EXPLOSIVECHEMISTRY.Allen L. Olsen, Instructor of Chemistry. Kansas State College, and John W. Greene, Head of Department of Chemical Engineering, Ransas State College. John Wiley & Sons, Inc., New York. 1943. vi 106 pp. 8figs. 13.5 X 21.5cm. 61.75. This is a manual for use in connection with the laboratory part of a short course in explosives such as might be given, in an ardinary college laboratory with but very little extra equipment, as part of the Engineering, Science, and Management War Training Program. I t contains about the minimum of directions and information, and is not sufficient hy itself without an instructor to work beside the student and without lectures to interpret and to explain the directions. The several chapters deal respectively with: I, Safety; 11, Propellants, Raw Materials; 111, Propellants, Nitrccellulox, and Smokeless Powder; IV, High Explosives; and V, Primen, Igniters, and Initiators. An appendix discusses sampling. Safety precautions are discussed adequately, hut no very dangerous experiments are described. Some might think that more explosive experiments ought to be included in the course, say, the lead plate test of detonators and determinations of explosion temperatures, of sensitivities in the drop test, and of velocities of detonation by the Dautriche method. Such experiments would supply interest-and discipline. Also lacking from the hook are chemical experiments with the lesser-known explosives, and instructions in the art of becoming acquainted with the properties of an explosive concerning whose peculiarities one has not been informed in advance. The book contains clear directions for the laboratory determinations usually made upon the powden and explosives which are in common use by the U. S. Army and Navy, and i t tells what the specificationsare for these materials. But the book does not in general explain the chemislry which is involved in the determinations or in general tell why the specifications are what they are. These matters presumably are covered in the lectures which accompany the laboratory course. The chemistry is immutable. let it be remembered. but the soecifications are subiect to change and repre'ent compromiws hctwwn two variables, be1 w e m what is desiwd und what n m y Iw n w r r d econonaically on TPNNIIY L. IJAVIS an indurtrial scale.
CHEB~IST~Y MADEEASY. Volume One-THE THEORYOR INORGANIC CHEMISTRY.x 184 pp. Volume Two--ELEMENTS AND COMPOUNDS IN INORGANIC CHEMISTRY.vi 232 pp. Volume T h e - T H E ALIPHATICAND AROMATIC COMPOUNDS OR ORGANIC CHEMISTRY.vi 256 pp. Volume Four--CnE~rc~Ls oa COMMERCE. viii 542 pp. Cornelia T. Snell and Fop& Dee Snell. D . Van Nostrand Company. Inc., New York, 1943. Each vol. 14 X 20.5 cm. Illustrated. $7.95 per set. According to the preface, these books are designed for the "man or woman who wishes a well-rounded scientific education by home study without a teacher." The authors have avoided a stiff and rigorous textbook treatment of chemistry by humanizing the subject with illustrations from everyday life, putting "first things first." and progressing step by step until this objective has been accomplished. The theory and underlying principles of chemistry are c o w e d in volume one. Simple experiments are discussed which may be performed by the reader. Each chapter is concluded by a set of test questions and each volume contains a final examination. Volume two continues the study of chemistry by introducing the more important elements and compounds, while volume three is devoted t o organic chemistry. The last volume differs f m the first three in that it is more of areference book containing a list of industrial chemical and commercial raw materials. It is included in the set that the reader may have a t hand an informational volume on the usefulness of materials. Excellent glossaries are a part of each text. The reviewer has found the style of these books such that the reader will enjoy his home study and will come away with a clear-cut picture of this interesting field of science and a definite amount of knowledge. GRETAOPPE
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HrOn S c n o o ~ GALYBSTON. TEXAS B1LG
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ORGANICCHEMISTRY.William T . Caldwell. Temple University, under the editorshin of Hermen T. Briscoc. Indiana Universitv. Houghton Mifflin 6ompany, Boston, 1943: x 763 pp. 15 j( 23.5 cm. $4.25. This book has been written with the purpose of providing in one text an adeouate treatment of orranic chemistrv for the beginning student, and is dr.igned to c n n y one who has a kuowledge of gcnrral inorganic chctnistry to a point nhcrc he can profitably u.c advanced texts denliug with specialired topics and the original literature of organic chemistm. The author's point of view is reflected in the editor's introduction. "The student of organic chemistry finds a vast collection of information . . . if his study is to be comprehensive in scope. It is no longer possible to place before him a simple outline the author need not apologize . . . for the quantity of material that he has ~rovided." The author's treatment is comprehensive, the b w k being of much greater length than the average introductory text. It is comparable in number of words to Whitmore's "Organic Chemistry," though written in textbook style rather than in an attempt to make of it another "one-volume Beilstein." - I t is easily read, and the degree of advancement of the student is keot in mind. However. because of its verv scooe and detail. it drhitely ttceds consider& "traching." ivithout this, even the good studerlr might become bogxed down by thc wealth of material offcred. It would be a Letter first text for those teachers who believe in a very comprehensive full-year course far seniors than for those who prefer that undergraduate organic chemistry be given in two years. It is only fair t o the author to say that the reviewer happens to prefer the latter plan, believing in a f i s t broad course in fundamentals followed by a second course of greater detail. The coverage of the book is excellent. Few topics, indeed, which an undergraduate should study are not well covered.
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