A Laboratory Manual of Organic Chemistry. Third edition (Williams

A Laboratory Manual of Organic Chemistry. Third edition (Williams, Roger J.; Brewster, R. Q.) ... Third edition (Fisher, Harry L.) Journal of Chemical...
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RECENT BOOKS E s s s N r r ~ ~oa s CHEMISTRY.Gretchen 0.Luror, B.A. Department of Nursing Education, Cass Technical High School. Detroit, and Florence Oram, B.S., M.A., R.N., Assistant Director, School of Nursing, Michael Reese Hospital, Chicago. Jean Broadkuml, Ph.D., Science Adviser, Professor of Bacteriology, Teachen College, Columbia University. Third Edition. J. B. Lippincatt Co., Philadelphia, 1938. xiv f 562 pp., including laboratory manual. Illustrations and diagrams. 13.5 X 20 cm. $3.00. The aim of this third revised edition is to present the basic principles of chemistry using practical applications from the nursing field, so that students of nursing shall have a foundation on which to build their other studies, and to give them an appreciation of the growing importance of chemistry in all phases of life. ~ l m o s half~of t the material is concerned with inorganic chemistry, while the second half deals with organic chemistry. There is an endeavor to present the material so that it will be usable for students who have had some chemistry previous to their entrance in the school of nursing, as well as for those who

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The reviewer feels that the authors have written an excellent textbook for nursing students and have accomplished their stated purpose. From the hright end papers with their reminder of modem chemistry's progenitor, alchemy, through the last few pages in the Laboratory Manual for the instructor's use, this book retains its appeal. I t is replete with aids for teaching, and facilitating the learning of students. The reviewer finds her students appreciate the "Personal Word" preface and the Preview of each Unit. It also seems t o her t o be a better plan to start with necessary definitive explanations concerning atoms, their structure, molecules, formulas, valence, and equations and then proceed t o oxygen, hydrogen, and other important elements and their compounds, than to begin with water, oxygen, and so forth, as many books do. Abundant dark-type topic headings should foster studying with a purpose and make reviewing easier. Other features which make this a good textbook are, simple, but comprehensive previews a t the beginning of each unit, factual reviews opening many of them, and detailed summaries,ending each unit, and these last, also, have emphasis placed on key words by darker t w e orintine. c There is an abundance of question material for self-testing and group examinations, both of the essay type and the newer objective type. This is a good textbook for schools of nursing for many reasons. (1) I t follows the suggested outline in the Curriculum of the National Leame of Nursing Education, which is trying to insure a t Least minimum standards in nursing schools. (2) The time allotted for chemistry in schools differs from a minimum of twenty to thirty hours fixed by the state to ninety or one hundred hours in university nursing schools, and I have found this book adaptable to these variations. (3) The emphasis throughout is on elements and compounds particularly useful in therapeutics with, in many cases, explanations of why they are being used and their effect. (4) Part I1 "Organic Chemistry'' puts less stress on memorizing of structural formulas and more emphasis on physiological chemistrv.. and the need for nurses to have a scientific basis for their knowledge about, and use of, carbohydrates, fats, proteins, vitamins, anesthetics, and w forth. The reviewer has tried t o keep the teaching of Units Ten through Fourteen concurrent with the study of the digestive. excretory, and regulatory systems in anatomy and physiology and has been encouraged by the results of this, over previous programs.

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The illustrations and diagrams are clear, well placed, and valuable. The reviewer has, however, wished for more of them, finding it necessary often t o use other books as illustrative references. In our small school, we have found that the Laboratory Manual fits our situation quite well. The experiments are sufficient in number to demonstrate the concepts, and the equipment suggested is not too elaborate or expensive. The reviewer would heartily recommend this hook to be used a s a textbook in schools of nursing. She thinks it would also lend itself well to the teaching of home economics students. Inrs A. JETTE,R.N. S ~ R DM Y B Y O ~ AH I. O S ~ A L ATTLB~OXO, MASSACBUSBTTS

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MANUAL

EnMIS TRY,

I.

and R, O, B,eurrUr. D. Van Nostrand Company,

New York City, 1939. Third Edition. 26 figs, 14 22 cm, 8,00.

xiii

+ 217 pages.

This manual is "suitable in spirit and content t o be used with" the senior author's I N ~ ~ O D UTO ~T ORGANIC I O N CA~MKSIRY, to which references are made throughout the bwk. I t is intended primarily for students of first-year organic chemistry who may have limited hours for work, and for this reason many of the exercises are of such character that they can be completed in one laboratory period. There are, however, some longer experiments, such as the malonic ester, acetoacetic ester, and Skraup syntheses. The two hundred eight pages of text are apportioned as follows. A oreliminarv section of fourteen vanes is devoted t o exercises on some eenerailaboratorv on he rest of the test oresents ~ -"~~~~~~~~ ~ ~ ~ - oneration;. , succcssivcly one hundred thirty-wvcn exercises (one hundred SLY pages) in aliphatic chemirrry, scventy-eighr rxcrriles (,evenlyfour pages) in aromatic and heterocyclic chemistry, and finally a brief introduction t o organic qualitatiye analysis, occupying thirteen pages, of wpch six are devoted to tables of compounds. A three-page appendix gives directions for preparation of some special reagents, a table of densities and boiling points of some organic liquids, and an abridged table of atomic weights. The index occupies five pages. The experiments illustrate the reactions and methods of preparation appropriate t o an elementary course. I n any ordinary course it will be necessary t o include only a selection of the numerous experiments described, some of which present alternative procedures. To assist this selection there are given two lists of experiments, grouped into three-hour periods, and suggested as suitable for shorter and longer courses of thirty-four and sixtyeight periods, respectively. The experiments are on the whole conventional, most of them appearing in other familiar manuals. The number of brief experiments of the test-tube variety, including some rather special tests, appears to be relatively large. In earlier preparative experiments yields are not emphasized and are sometimes not mentioned; later experiments usually state definitely the yields to be expected. Several individual features may be mentioned, ois., the use of the modified Castellana decomposition preliminary t o the qualitative test for nitrogen; a test for peroxide in ether; the inclusion of a number of exercises on separations of mixtures and preparations of identifying derivatives, which serve as preliminary studies for the work in qualitative analysis; experiments illustrating various kinds of dyeing (direct, mordant, ingrain, vat, pigment); and the following preparations: ferf.-hutyl chloride, dimethylglyoxime (using in the second step an extemporized solution of hydroxylamine sodium sulfonatel. -~~~~~ , nrea-formaldehvde resin. iodobenzene from benzene by action of iodine and nitric acid, phenol-formaldehyde resin, benzophenone by Friedel-Crafts synthesis from benzene and carbon tetrachloride as an alternative to the preparation using benzoyl chloride, and quinone by hromic acid oxidation of hydroquin~~

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one. The experiments on cyanides, proteins and carbohydrates are more numerous than is usual in elementary manuals. A commendable feature of the ethyl acetate experiment is the inclusion of the comnositions and hoiline- ooints of constant-boiline mix. turcs of &I acetate, alcohol,nnd water. This will euplak, and bell, to avoid, a difficulty often encountered by students. 'l'he usrfulne.* or nppropriatcnes.; of a few erpcrimcnts may perhaps be questioned, e. g , three methods for making methane; the test for formaldehyde in milk; the preparation of formic acid from ovalic acid; two procedures for the preparation of thiocarhanilide; the preparation of phenyl isothiocyanate and triphenylguanidine; the henzilic acid rearrangement; the purification of benzene; the preparation of phenylmethylpyrazolone; the preparation of iodohenzene dicbloride. The procedures are in general clearly described. The object of each exercise, if it is not made ahvious in the heading, is stated briefly a t the outset. Several chapters are introduced by reaction charts which indicate the transformations t o be effected. Many experiments include interpolated questions (to be answered in the notebook) designed to induce the student t o think. The apparatus required will present no problems. The less simple outfits are shown by line drawings. The use of a heated funnel for filtration of hot solutions prior t o crystallization is not mentioned. There are a few places in which the directions appear to he insufficiently explicit. Thus it is stated that melting-point tubes should he "about 1.5 mm. in diameter," and that the melting point is the "temperature a t which the substance begins to melt." I n the test for halogen in presence of nitrogen and/or sulfur "a portion of the filtrate is acidified with nitric acid and boiled," directions which some students may follow faithfully (if not intelligently) and still get a fallacious test for halide. The distinction between methyl and ethyl alcohols, based on the formation of the salicylates, one of which "may he identified by its odor." seems t o need some clarification. The directions for the preparation of tribromophenal do not mention the formation of tribromaphenoxybramide nor provide for its reduction. The Schotten-Baumann reaction is so presented that a student taking the short course may conclude that this named procedure is limited to preparation of henzoic esters by use of benzoyl chloride. The authors have not been consistently careful with respect t o the inclusion and the strategic placing of directions for avoidance of fire and other hazards. The first explicit information as to a safe pmedure for recrystallization from volatile and in!Jammable solvents is given following the preparation of m-dinitrobenzene, a n exercise which is omitted from the short course and is normally reached in the long carmse only in the forty-second period. Crvstallizations fram inflammable solvents are directed in a number of a r l i e r cxperimcnrs (mcluding thkfirst experiment in the manual), in one case with a parenthetical caution, but irr no case with a crass refcmnce to the uplicit dirccrium in the later section. The experiment on the preparation of methyl cyanide fmm acetamide (twenty-third period) includes a caution with respect t o burns from phosphorus pentoxide, which information is withheld in several earlier experiments in which phosphorus pentoxide is used, uiz.,in the preparation of ethylene (optional exneriment for the fourth neriod) and in drvine ether for the Grienard reaction (fifteenth period). The student is directed to keep his anhydrous ether over sodium metal, but is given no suggestion as to a safe procedure for the eventual disposal of the residual sodium, though this operation involves probably the most serious single fire hazard in the student laboratory. The poisonous and irritating properties of phenylhydrszine are mentioned in the experiment on osszones, but are overlooked in the directions for the orenamtion of nhenvlhvdrazine footional about seventeen , periods later), involving isolation of the base by extraction in ether. A degree of caution which seems excessive appears in the experiment on ether, where the impression is created that the preparation of ether is hazardous and is advisedly done as a demonstration by an instructor. In the opinion of the reviewer the student should perform this experiment as a valuable lesson in the control and cobrdination of experimental conditions. The fire hazard should he no greater than in ether extractions, crystalliza-

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tions from imlammahle solvents, and disposal of sodium residues. The section on qualitative organic analysis suggests several steps in the preliminary attack (ignition test, determination of physical constants, elementary analysis, determination of the solubility group, and test for acidic or basic character using "universal" indicator paper), but the selection of the further procedures is left t o the student, who has already done some experiments (in the preparative course) on separations and on preparation of derivatives. The "unknowns" are selected from a lint of one hundred thirty-one compounds, representing most of the classes studied. Many of these compounds will have been encountered previously in the course and should he easy to identify. The comnounds are tabulated first in annroximatelv the order in . which they appear in the organic text, with the soiubility group indicated for each compound, and then in the order of ascending melting points of solids and of ascending boiling points of liquids. "No attempt is made to present a 'fool-proof' scheme of analysis which will make mental effort and alertness unnecessary. It is expected that students will make mistakes hut that they will learn as they proceed." The index lists principal topics and compounds made or studied. I t is brief, and does not consistently include processes, apparatus, and reagents. The omissions are probably unimportant in a hook of this type. The text is not as free of typographical errors as would he expected in a third edition, though the number and the character of the ermrs are not such as t o mar the book. One misspelling by no means peculiar t o these authors involves the name Tollens. There are no less than twelve appearances of its possessive form as "Tollen's." The reviewer is not well enough acmainted with oreviaus edtrions of thc manual to estimate the amount of rcvision represrnrrd by the third edition. The changes mmtionrd in its prcface include the omission of some eypcrlmcnts of doubtful value and the substitution of several "improved preparations," many changes in detail in the text, and expansion of the section a n qualitative analysis. The book has many merits, can unquestionably he made to serve as the essential guide for a thorough elementary laboratory course, and has enjoyed a deserved success. The book is bound uniformly with Dr. Williams' textbwk, and is printed on r%ther soft paper:. The publishers' admonition (following page xiii) t o the student to keep the manual in his reference library may he applauded in principle but is perhaps not altogether ingenuous. The reasons advanced are not wholly valid in the case of a n elementary laboratory manual (which is not a "textbook" and which has not been "studied from cover to cover") but if the notice helps to curb the traffic in second-hand lahoratorv manuals fa result oossiblv not unforseen bv the nubI~ihers)it will a190 aid teochcrs of organic cbcmistry, in whose cuurscs the scnsonal renppearnnces of used manuals, frcely and often inaccurately annotated by previous owners, constitute a deterrent to accurate work, careful observation, and cerebral activity. E. C. U'Aomn

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U N l V B B S I N OP PIINNSYLVAN,* P " , L A ~ ~ L F PBNNSYLV*NI* ~,*.

LABORATORY UNITS IN CHEMISTRY.William McPhcrson and Ed Henderson, Ohio State University, and George Winegar Fouler, School of Education, Syracuse University, and Supervisor of Science, City Schools, 329 pp. Ginn and Company, New York City, 1938. xii 68 figs. 17.5 X 23 cm. 5.80.

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LABORATORY UNITSIN CHEMISTRY is a laboratory manual and study guide for high-school chemistry. The manual is especially designed to accompany the book, CHEM~STRY AT WORK,hut may be used with other texts. The book contains fourteen units, the nature and purposeof which can be best portrayed by giving some description of the divisions within each unit. Each of these units is composed of t h e following sections: Question Survey. Study Outline, Optional Work. Unit Readings. Problems. Helps