RECENT BOOKS I . ~ a l t ~ r ~IL.THODSOP ox~ ORGANIC CAWISTRY. L. (;oltemmnnn. Rcviced by Ileinrirh M'icland. Translated from the twentyfuunh G w m m edition bv 1V. dfcCorln~v. The Marmillon Company, New York city, 1937. xvi i435 pp. 59 figs. 14.5 X 21.5 cm. $4.50. The present edition of this excellent laboratory manual retains the characteristics which have marked i t throughout a long and honorable history. A book which har passed through twenty-four editions during a span of over forty years has small need of an appraisal, and an extended review is perhaps supererogatory. The noteworthy features of "Gattermann" are familiar, &s., considerable diversity of experiments, and supporting sections devoted to explanation and extension. As is stated in the older preface (page vii), and as is obvious from the nature of some of the discussions, the manual is designed especially for the use of students who are already acquainted with the essentials of organic chemistry, though by a careful selection of experiments and of appropriate explanatory material the b w k can, of course. be used profitably by beginners. The principal sections deal with general operations (pages 1 to 42), organic analytical methods (pages 43 to 87), preparations and discussions (pages 88 to 417). and hints on the use of the literature (pages 419 to 422). The preliminary section on general operations is suitably brief and elementary, which is much to be preferred to an elahorate and detailed account of such matters a t this point. I t would seem proper, however, t o advise the student of the hazards involved in the use of a vacuum desiccator containing concentrated sulfuric acid. The process of fractional distillation is merely outlined, nor is there a t any later paint any exercise in which this important process is adequately illustrated or described. There is no mention of corrected thermometric readings anywhere in the book. The most striking change in the new edition is the analytical section, which has been placed on a "meso-analytical" (semimicro) basis. This is t o be welcomed, and is representative of the present tendency among organic chemists. Most of the methods described are adaptations of Pregl's pmcedures; their development is credited to F. Halscher. The procedures are well presented, with the limits of accuracy stated. Nitrogen is determined by the Dumas method; the Kjeldahl method is not mentioned. I n the determination of carbon and hydrogen lead dioxide is replaced (in the tubefilling) by reduced copper; this substitution probably makes less serious the omission of any mention of a blank analysis. Halogens are determined by the Carius method, and as an alternative an adaptation of the Pregl decomposition is described, chlorine and bromine being titrated with the aid of an adsorption indicator, and iodine by the iodideiodate method. The Carius and Pregl methods are used for sulfur. Alkovyl groups are determined by the Vieback and Brecher method. There are described also the determinations of acctyl and hencoyl groups. The determination of molecular wights by the method of Rast, and thc macro-determination of nrtivc hydrogen by use of mcthyl magnesium iodide are retained from the previous edition. The experiments and the accompanying discussions (three hundred twenty-nine pages) cover a wide range with respect both to subject matter and degree of difficulty. The selection of ex~erimentsreflects the extensive exoerience and wide interests #,I the authors. Almost all the importnnt reactions nud prepnrutwc mcthods, and many of sccondnrs importance, arc illusrratrd by one or rnorc uperimcnts, and other9 are recommended to the student in the extensions. There appears t o be no mention of the ULlmann reaction. I n this edition the manual presents an experiment on chromatonraphir adsorotion, in which there are revealed to the student
some of the well-concealed beauties dormant in the leaves of the despised, albeit energizing, spinach. There is also an example of ozonalvsis (adioic aldehyde from cvclobexene). A few exoerimerits-in the preceding~editionhave been dieted. ~ x c e p for t these changes, and several modifications of procedures, the experiments are about the same as those in the previous edition. The experimental procedures are well described and, in general, are wisely chosen. I n some cases older methods are retained (as for preparation of phenylhydroxylamine. quinoline, and furfural) although better methods are nowavailable (e.g.. in"0rganic Syntheses"). The recovery of alcohol following fermentation appears to represent a singularly ineffective fractionation, for after three distillations through "an efficient column (Raschig rings)" the alcohol is of less than thirty per cent. concentration. I n the experiments on the preparation and use of diazomethaue and on isolation of nicotine no mention is made of the toxicity of these compounds. The ozonization experiment includes no description of the ozonizer, though in many laboratories i t would be necessary to build this apparatus. The "theoretical" sections are valuable as a means of broadening the student's viewpoint and of providing him with essential information. These sections make "Gattermann" the most explicitly informative student manual known t o the reviewer. On the other hand, i t seems that some of the experiments and explanatory material deal with matters of rather restricted interest. I n certain of the discussions the student is led somewhat far afield among reactions which are interesting hut exceptional and of perhaps doubtful appropriateness in a student laboratory manual. This is the case with part of the material on nitmmethane and derived compounds, phenylhydroxylamine, dehydracetic acid and related pyrones, and phenyldiazonium perbromide, and with the four pages devoted to ethyldiazaacetate. I n view of the degree of familiarity with chemistry assumed elsewhere in the book it seems unnecessary to include so elementary an account of the application of the mass-action principle to the process of esterification, addressed apparently to students who have not yet heard of reversible reactions. The discussion which accompanies the preparation of ethyl acetoacetate gives only the Scbeihler explanation of the reaction. ignoring the protests of Adickes and the explanation offered b y McElvain [J. Am. Chem. Soc., 56, 1173 (1934)l. The quinaid structure is assigned to "tribromophenolbromide," with no mention of the contrary findings of Lauer [ibid., 48, 424 (1926)l. In the account of the Grignard reaction there appears the unqualified statement that aryl halides yield Grignard compounds, without calling attention to the unsatisfactory behavior of chlorides [Gilman and St. John, RCC.trm. ckim., 49, 717 (1930)l. The Grignard synthesis is called a "synthesizing hydrogenation." an artificial designation which places undue emphasis on the "hydrogenation" and too little on the alkylation. Attention is not directed to the alcoholate character of the addition compound, though recognition of this fact is helpful to students. On the whole, the account of the Griguard reaction is perhaps the least satisfactory discussion of an important matter in the book. The three-page explanatory section which follows the experiment on isolation of bemin from blood seems not whollv in d c e~in ~a ~r a~ laboratory rnnnlval This experiment, that on chromatugraphic anilly4*, and thc final c ~ p c r i m mon t the bile acids and cholcsterul, bring the preparative part to an impressive conclusion, and emphasize the fact that this manual can be used to advantage by students considerably beyond the undergraduate stage. The short section on the use of the organic chemical literature deals almost exclusively (and very sketchily) with the German formula indexes and with the Beilstein "Handbuch". The terminal date of the third edition of Beilslein is given as July 1, 1899, and the number of volumes probably to be required for the fourth edition is optimistically put at twenty-five. The onlv
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journal mentioned is Chemisches Zmztralblatt. The wholly German character of this section is perhaps not surprising in the original, but i t is to be regretted that the English edition fails to commend t o the student such valuable works as Chemical Abstracts, British Chemical Abstracts and "Organic Syntheses". The discussion of the literature is followed by a list of supplementary preparations for which directions are t o he sought in original papers. The hook is excellently printed, with few mistakes; ten were discovered in the reading of perhaps eighty per cent. of the text. The translation in some places retains the unmistakable flavor of the German orizinal. The line drawings are clear, but would win no very high grade from a teacher of mechanical drawing. It is hoped that the foregoing critical account will not misrepresent the high opinion the reviewer holds of this laboratory manual as a guide for students of all stages of advancement. The careful examination of this new edition was a profitable and pleasant experience. If "Gattermann" needs a recommendation i t is heartily given. E. C. WAGNER Umvsxsrm on P s n r s u L v A N r a P ~ ~ A D B LP- B AN . NS~VANIA
S m a a I c T s w s FOR USE IN TEE "QUAI.." COURSE. Wayne E. White, Research Fellow, University of Kansas. Lawrence, Kansas. Private Publication. 1937. 14 pp. 15 X 22.5 cm. $0.25. A pamphlet of a few pages devoted to instructions t o the student for carrying out specific tests for ions in original solutions of unknowns encountered in the usual course of qualitative analysis. The ions considered for such tests are as follows: bismuthons, ferric, ferrous, barium, stannous, stannic, manganous, nickelous, cobaltous, aluminium, chromate, and zinc ions. Directions are also given for the preparation of the organic reagent solutions. Sets of these reagents may be obtained from the author. WARRENC. JOANSON Uwzveaszm or Cmc~eo c m c * o o , ILLINOIS
of such a course. There are numerous examples of bad spelling -probably typographical e r r o r s a n d of word usage. The latter is quite pardonable in view of the author's own statement. Inaccuracies in statement are not numerous. Perhaps the most important are found on page 46. Percentage concentration is erams solute oer one hundred -erams of solution. The abuse of this term is all too frequent in the literature. The author discusses thisand other wages, hut fails to emphajize the currcct mcaning. Molar and normal colutiona a m m d s or equiwlcnts per liter of solution, instead of per liter of solvent as given. The book presents numerous instances of beautifully clear presentation of abstruse ideas. Even a novice can grasp them. For this alone it merits examination by those teaching similar courses. Professor Tanchoco is t o be commended also for his insistence on the sneculative nature of manv of the new conceots. The following is tyl,ical. "IIowcvcr, this theory is far from twing perfect as it is true only of a fictitious ideal solution or of inrmitc dilution, and it is llarticularly disconcerting that the theory fails when it is most needed." In conclusion it may be stated that this work meets the need it was designed t o fill and can probably furnish ideas on presentation to others. MALCOLM M. HARING
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U m n s m on M A ~ Y L A N O COU-BOB PIPE, M * B ~ * N D
IILRM~.STAKY PHYSICAL CREMISTK~. Hugh S. Toylor. h ; i d B. Joloner P r o f c s ~ rof Chemistry, Princeton I:niverrity, and II. Auslin Torlor. Assistant Profewx of Physical Chemistrv. New York university. Second edition. D. Van ~ o s t r a n d Company, Inc., New York City, 1937. xiii 664 pp. 112 figs. 13.5 X 21.5 cm. $3.75.
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This second edition of this text attempts to include an elementary presentation of those aspects of the subject which will enable the student t o appreciate the present-day developments in the science. I n order t o accomplish this, the authors have introduced the development of the quantum idea and applied i t to atomic and molecular systems. I n addition, the treatment of the easeous state and of reaction velocitv * is from a modern point of view. I n the opinion of the re\.iew~r,these changes are very stimulating and should increase the interest of the studmt, as well as the teacher. I t is rrfrcshiug to find a texrbouk in physical chemistry so up to date in these topics. Fmm an educational point of view, the inklnence of research on teaching is significantly illustrated, in that those topics which are so well presented are those with which the authors are actively associated. On the other hand, this high standard is not maintained in other topics. The chapters on solutions, electrical conductance and ionization, and ionic equilibria do not reach tlie high standard set in the other chapters. I n particular, the treatment of transference numbers and conductance is somewhat disappointing. Nevertheless, the authors have bmught forth a hook which in many respects is superior t o the texts previously available and merits the attention of progressive teachers in the field. The reviewer noted onlv one inconsistencv in the oresentation. The treatment of reacrmu vclwity on page 518 is incon&tmt with the trralmrnt on page W2. ThcclTect ofelccrrolyte on the equilihrium ron*tant is present in both caqw MARTINKILPATRICK ~~~~~~
Pwsxwu. C~MISTRY. F. Tanchoco, A.B., Ph.C., LI.B., Pro. fessor of Chemistry, Manila College of Pharmacy. Benipayo Press. Manila, P. I., 1936. viii 173 pp. 21 X 27 cm.
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"This b w k was written for beginners and especially far the Freshman class of the Manila College of Pharmacy. by one who possesses only a working knowledge of English." This quotation from the foreword furnishes the key t o an understanding of the hook. The title is somewhat of a misnomer. "Introductory Chemistry" would he more descriptive, since "the book is intended t o serve as constant reference material during the subsequent studies of Descriptive Inorganic Chemistry, Organic Chemistry, and Analysis." It is somewhat analogous t o the texts, eti., used in v&ous pandemic courses in this country. As in mimeographed texts, only one side of each sheet is printed, the other side being used for lecture nates and sketches of which there are none. Subjects considered are Matter and Energy, Gravitation, Hydrostatics and Hydrodynamics, Heat, States of Matter, Solutions, Cdloids, Cohesion and Adhesion, Affinity, Atoms and Molecules, Valence, Atomic and Molecular Weights, Thermochemistry. Electricity and Magnetism. Ionic Theory, Electrical Nature of the Atom, Theories of Atomic Structure, Types of Comoounds. X-ravs.. Radioactivitv and Nomenclature. Three nppendires are included: a tahle of water-vapor prrvsurts, the common demcnts grouped hy fwnilies with thcir valrncrs, and a tahle of atomic weights. The hook is devoid of mathematics. The author's selection of subjects for an introductory course is open to criticism, althouzh their interest-arousim value is unsuestianed. However. there is a t present no general agreement on the desirable content
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UNIV~RSITY OF PBNNSYLYA~A PAIL*D.LP~*.
PBNNSYLVANI.,
AL-RMIS BUCH,GEHEIMNISDER ,GEHEIMNISSE,mit Einleitung und Erlautemgen in deutscher Uhersetzungvon Ju1iu1 Ruska. Quellen und Studien zur Geschichte der Naturwissenschaften und der Medizin, Band 6. Verlag von Julius Springer, Berlin, 1937. xii 4-246 pp. 5 figs. 17 X 26 cm. RM 38.50. I n the opening paragraph Razi (Rhazes) states that he wrote this book for one of his young students who asked him t o compile something concerning the performance of the secrets of the
