structure be accepted, it cannot be considered as established until verified by synthesis through reactions of known course from intermediates of known structure. Furthermore, the bond formula is not configurationally elaborated. The present compilation is s. collection of twenty-nine chapters representing the scrambled, almost hysterical, efforts of perhaps a thousand workers in the laboratories of government, industry, and university in this country and in England. This is socialized science with a vengertnoe and is a far cry from Geheimrat Emil Fischer and his staff of eight boys. The repo~tis a mixture of primary and secondary literature and will be a headache for the abstmctors. Preferable it would have been to have released the results in due time and allowed them to be incorporated in the usual channels of the primary literature. Then a monograph could have been written so that "he who runs might read!' The student can readily note the introduction of a sense of stability into the early frantic effortswhen Wiutemteiner and coworkers put sodium benzylpenicillin on a crystalline basis and established the presence of sulfur in the molecule. From there on the degradative experiments readily proceeded to fruition on application of the proper method, in this case the reductive desulfuriaation of Bongault, Cattelain, and Chabrier. A massof other data was evinced and an array of pertinent physical measnrements, especially those obtained by X-ray difiraction and infrared absorption, became available. The favored solution (I, 6 acylamino - 3,3 dimethyl - 7 - 0x0 - 4 - thi - 1 - aaabicyclo[3.2.0]heptane-Zcarboxylic acid) contains an acylamino sidechain on a bicyclic structure consisting of a p-lactam ring fused to a thiazolidine ring; a formula for which no pertinent model substances are presently available. The linkage 1,7 is extremely labile and the reviewer favors the Robinson viewpoint that this may be the seat of prototropic tautomerism, such as is illustrated in 11.
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figuration" on page 538. The physical chemists are better informed (page 349). The high cost of this book will fairly limit it to institutional libraries but in these archivesit will bear witness that the human raceean salvage from a destrurtive w a r dart a grent entcrpri+c to make availoblc a substance n.lai,!h is a uew agent in rhc fight against the ra\.age of discase and is the forcwrrrr of an arm\. of M. L. WOLFROM
A LABORATORY BOOK OF ELEMENTARY ORGANIC CHEMISTRY
Alexander Lowy, Late Professor of Organic Chemistry, a d Wilmer E. Baldwin, Associate Professor of Organic Chemistry, University of Pittsburgh. Third edition. John Wiley d Sans, Inc., New York, 1949. xi 186 pp. 7S figs. 22 X 28.5 om. $3. Spiral bound, paper cover.
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THIS is a dificult book to review. While some sections are excellent, just enough experiments are open to criticism to put this manual in the "recommended with reservations" c l w . The type of information in the introduotion should be in every elementary o r g a ~ cmanual. Yet the reviewer feels that only an instructor with many years of experience could adequately use this manual. To prevent a prejudiced report the reviewer laid the manual aside for over a month, but on re-evaluatiou the same conclusion was reached. Unfortunately as the reviewer criticdly read the experiments he found it necessary to take issue with the writers on point after point. (One has the uncomfortable feeling that not sufficient care was put into this edition.) Examples of some of the points leading to criticism are: In experiment 1 the separatory funnel is used and no suggestions for its use offered; the instructor must fill in. A reierence is made to experiment i o n page 72, but this in turn refers to experiment e, page 68. Experiment 2 contains a qualitative test for halogens. The directions fail to tell the student to bail the solution after acidifying and before adding the silver nitrate; thus the test works for the specific compound tested, but will not be a general test far halogens in an organic unknown. In experiment 3 concentrated sulfuric acid is used as the bath for melting points1 The correction formula for the thermometer readine ..is eiven. and a statement is made that the constant 0.00015, k the roeficirnt of expansion uf nlerrury. Tlrc handbook do not corrobornte this. I n frartionation no nt. tempt ih ~nndeto differentinte rnol-per cent and weiglrt+rr vmt. ks one reads more experiments he h d s that the experiment of hydroxy acids is merely an experiment on acids. The student is told in each case that the acid in question is a hydmzy acid. Even the new experiment added for this edition is open to criticism. Of the various ways of adding the reagents for the synthesis of acetaldebvde in method one., a aualitative review of rrttea ~~~of competing rcwtions would ~ L o nthat this i.i nut the best of the alternatives. Conmcnts can also b~ m d e on a few other ex~wirncnls; this docs not mean, however, that the majority of the experiments are open to criticism. There is a constant necessity to explain this or demonstrate that, requiring that even an experienced instructor he always on the alert. In fact the preface states: "Certain theoretical ex'planations, equations for reactions, and data are omitted in order to stimulate students to seek information from textbooks and handbooks (listed irt the Appendix) or from the inqtrurrur." Rut most students must read as well as hrar exylulitions. It is on constant rereadlug that thestudrut leuus. At this leveldtudenta are not able to take good notes. Where the book is good, it is very good. It starts with an excellent section in "Notes to students!' Here some good sound advice is given on observations, laboratory strategy, notes on a p paratus, chemicals, etc. Before any experiments are permitted the student must show that he is familiar with these contents.
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It is almost unbelievable that the powerfultool of polarimetry was not applied to a study of such a transformation and its possible variation with environmental aciditv-basicitv. Throunhout the work insu5cient attention was paid io the accurate estahsbment of polarimetric data. A unique point in the formulation and one wbich caused no end of initial confusion was the remarkable variation in the nature of the side chain (R in I and 11) obtained by suitable alteration of the nutrient medium. Most of the degradative work was done on beneylpenioillin or penicillin-(: (R=CsHsCH-) but ten other penicillins are described herein, some of which may be of commercial importance. There sre three asymmetric centers in I. Position 5 is uncorrelated. Position 6 has been correlated with h(dex1ro)-&nine and position 2 with unnatural or (1euo)-vdine. But vsline has not been correlated with the reference standards glyceraldehyde and serine by an unequivocal method so that the relative configuration of this center is unestablished. Characteristic of the present-day confusion in the minds of organic chemists toward eanfigurationd matters, is the use of the term "absolute con-
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JOURNAL O F CHEMICAL EDUCATION
This is good. The range of experiments covered, 45 in all, shows good selection, and good arrangement with the more difficult experiments a t the end. The really difficult experiments are intentiondly omitted, for these would obviously be taken up in a more advanced course. Only a few minor changes in the experiments are made in this edition. Most preparations are aecomprtnied by qualitative tests, and quite often the student is asked to test his compound with litmus. This is pedagogically sound. The experiments on Fractiond Distillation (demonstration),, Fractional Distillation of Petroleum, Chloroform, and Destrnetive Distillation of Soft Coal are unique. One very attractive feature is the large numher of illustrstions, for in addition to representing most apparatus common to the laboratory, many eommercid counterparts are shown. A few flow diagrams for the eommereid methods of milking some of the compounds highlight t,he int,nre~t, t,he hook. . ~. ~ ~ of ~ . . ~ l'nicrttrnatrly the revieuw cnnnot recommend this book to nny but eq,rrienced teachera. One docs appreciate tlae toil an81 effort that goes into making a text and comes to this conclusion reluetantly. ~
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would do well to give this text serious consideration. If any fault could be found with this manual, it might he the fact that many directions and pieces of suggested apparatus are semiantiquated in terms of American practice. This is typically illustrated, for instance, with the absorption trains used in the quantitative carbon and hydrogen determinations. RALPH E. DUNBAR NORTR DAXOTA STATE COLZEBE FAROO. N O ~ DAKOTA H
MATERIALS ENGINEERING OF METAL PRODUCTS Norman E. Woldmoq Consulting Metallurgical Engineer. Reinhold Publishing Corp., New York, 1949. v 583 pp. 169 figs. 149 tables. 15.5 X 23.5 cm. $10.
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"THISvolume was written as a companion book to Metal Praeess Engineering, published in 1948. The latter book was eoncerned with the different metallurgical and meehanieal processes for fabricating metal parts such as casting, forging, rolling,, powARTHUR FURST der metallurgy, joining of metals, heat treatment, machinmg of ~ Tam U N I V ~ M IO~I.T8 b FRANCLBCO metals, ete. 8 m Fmcrsm, C ~ m o a m ~ "This volume presents the materials used in various type of industries and different applications in an attempt to correlate the metdurgy of the material with the engineering design and service applications. It has been written to meet the needs of PRACTICAL ORGANIC CHEMISTRY engineering students, profemional engineers, and production enI. J. Sudborough, formerly Professor of Organic Chemistry, gineers who can use the correlated and interpreted information Indian Institute of Science, Bangalore, and T. Campbell James, in part or as a whole with their professional work." Emeritus Professor of Chemistry, University College of Wales, The preceding quotation from the preface of Dr. Woldman's Aberystwgth. Blaokie and Son, Ltd., London, 1949. Second hook describes it aptly and indicates clearly the field of interest he edition. miii 450 pp. 99 figs. 24 tables. 12.3 X 19 cm. hopes to serve. He acknowledges his indebtedness to various 15s net. $2.12. sources for the material presented as the scope of his book is very THIS work, Iimt issued in 1909, is a laborstory companion to broad and no one person could a m all the information which the author is correlating and presenting. This book make3 Nndboroueh's edition of Bernthsen's "Orrrtnic Chemistrv!' Acrording to the authors the prerclrt edition LHHI , P P ~ rornpl~tely available, in one volume, information on competing materialsrevised in the light of long t x p r i e o w Likcaiw, a n endeavor hss as aluminum, magnesium, and stainless steels for structural servbeen made to inmrpurate rnoderri niethud* uf quantitative ice. In an analogous manner the materials from which gears analysis, new synthetic methods, and such processes of degrada- may he made is discussed and the proper treatments of these tion of organic compounds as are useful in the determination of materials are indicated. In the discussion of threaded fasteners structure. The text bas been reset, the illustrations have been design is discwed and the relationship between material and proper designing is emphasized. The interdependence of dereplaced or redrawn, and the whole modernized. A careful examination of this text and laboratory manual sign and material is stressed in several places in this book. reveals the fact that it is unusually complete and comprehensive. , "Materials for the Electrical Industries" in~ludesaninterestin~ Within the 450 pages are clear, definite, and adequate directions discussion of bimetallies and their properties. Magnetic m a t e for the preparation or study of no lem than 353 organic com- rials are discussed in a very understandable way and the theoriee pounds. The hook is divided into 38 chapters, each dealing of magnetism are presented in sufficient detail to form the neceswith a major division of organic chemistry. Besides the prepa- sary background. The section on Materials for Special and ration of numerous, varied, and typical organic compounds, Severe Service contains a very good chapter on corrosion and an the text treats extensively of such topics as oxidation, reduc- interesting discussion of materials for high temperature, high tion, polymerization, condensation, cyelization, molecular re- stress service. This section will be of interest to chemical engiarrangements, isomerization, reaction velocity, moleeulax weight neers and to mechanical engineers dealing with power plants. This book presupposes s. knowledge of elementary metallurgy determinations, and elementary organic qualitative and quantitative analysis. Each chapter opens with a. brief discussion of and therefore is not suitable as a text for the courses offered the the basic principles involved in the experiments that follow. nonmetallurgieal students in many of our colleges. I t would be While these introductions are brief in many instances, they are an excellent reference book for such courses and could be used as s text in a second course in such a series of courses. The price, specific and extremely helpful. This laborstory manual is one of the most complete and eom- $10, is going to make most htrnctors think twice before adopting prehensive of an elementary type that is readily available. Those it as a text. This is a very valuable reference book for a praoinstructors ushe the Bernthsen and Sudboroueh. "Textbook of tioing engineer who has oecasion to concern himself with metal products. Organic ~hemi&y," will find this to he a very oonvenient &d practical companion volume. Likewise, teachers looking for a JOHN T. MCCORMACK mare comprehensive organic laboratory manual than is usually Puzona U N I Y Z B ~ T T LAFATEWE.INDIANA found in the common elementary books produced in this country
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