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NEW BOOKS A Text-Book of Organic Chemistry. B y A . , F . Hollcman.

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from the Third Dutch Edition by A . Jamieson Ilfalker, Assisted by Owen E . blott. Second Englash Edition, Rewritten. 15 x 23 cm.; p@. xv 589. New York: John IT’zley & Sons, 1907. Pncc: $2.50,-A good deal of physical chemistry

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has been incorporated into this book and apparently with great success. On p. 25 w e find pressure-composition diagrams for systems of two miscible liquids having a maximum vapor pressure, having a minimum vapor pressure, and having neither maximum nor minimum. Perhaps in the next edition the author might point out that difference in boiling-points is not enough to make fractional distillation easy An even more important point is difference in the composition of the co-existing liquid and vapor phases. One more line in each diagram and a few more lines of text would have brought this out clearly. Since the organic chemist invariably distils under constant pressure, it seems to the reviewer that the temperature-concentration diagrams would have been more helpful than the ones actually used. On p. 27 we get a n admirable statement of the theory of distillation with steam. On pp. 28-30 there is a good statement of the theory of ‘shaking-out’ though the reviewer thinks i t could have been improved by the explicit statement that chloroform is preferable to either when the substance to be shaken out is more soluble in i t than in ether. So far a s the reviewer’s somewhat limited experience goes, each organic laboratory has a favorite solvent which it always uses regardless of whether it is the best in any given case or not. On p. 35 we find the synthesis of methane by means of pulverulent nickel. On p. 85 we get Menschutkin’s work on the rate of formation of tetra-alkyl ammonium iodides. On pp, 114-115 we have the dilution law in its application to organic acids together with the caution that it does not apply to strong acids. On p. 141 we have the equilibrium diagram for acetaldehyde and paraldedehyde. This is but a n earnest of what we may expect some day when organic chemistry shall really be studied in a systematic manner. On p. 159 under acetylene we find a reference to the limits of explosion for mixtures of air and acetylene, 3-82 yo acetylene; also a reference to the danger resulting from the presence of calcium phosphide in calcium carbide. If, the matter is to be gone into in such detail, a reference to the solubility of acetylene in acetone might well have been added. On p. 199 there is a brief mention of the decomposition of oxalic acid and the oxalates by light. On p. 237 we have the migration of the ions as illustrated in the electrolysis of. Fehling’s solution. On p. 345 is given Tafel’s work on electrolytic reduction of surine derivatives. I n a n excellent chapter on the carbohydrates there are some paragraphs on the formation of optically active substances which are worth quoting in full. “Investigation of the stereoisomerism of the monoses has contributed towards explaining the formation of optically active bodies in plants, while laboratorysyntheses usually produce the racemic forms; not, however, in artificial syntheses effected with compounds already having a n asymmetric structure. Man-

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nose, for example, yields mannoheptonic acid by the cyanhydrin-synthesis, and it would be expected! from analogy with other cyanhydrin-syntheses, that equal quantities of two stereoisomeric mannoheptonic acids would be formed. This is not so; only one acid is obtained, which shows that the building up of a molecule from one which is asymmetric can continue in an asymmetric sense. If an optically active compound were converted into a derivative with a greater number of asymmetric carbon atoms than itself, and if it were possible so to decompose the molecule of this derivative as to regenerate the original active substance, the residual part of the molecule would also be optically active. One ofitically active molecule would thus have occasioned the formation of another. “The formation of sugar in the plant has been proved by vegetable physiologists to take place in the chlorophyll-grains, which are composed of optically active substances. I t may be assumed that the production of sugar results from a combination of carbon dioxide or formaldehyde with these substances, their asymmetry making the sugar formed by the condensation also asymmetric. As the other constituents of plants are probably formed from sugar, their optical activity is easily understood, since they are formed from optically active material. “How the first optically active compound arose, and how nature has not produced the chemical-mirror images of all optically active substances found in the existing flora and fauna, since, as far as is a t present known, the probability for the formation of both must have been equal, are problems by no means solved by the foregoing considerations.” This quotation may serve also to illustrate the English style though it is only fair to say that the last paragraph shows the translator a t his worst. Wilder D. Bancroft.

Organic Chemistry, Including Certain Poriions of Physical Chemistry for Medical, Pharmaceutical, and Biological Studen.‘s. B y H D. Haskins and J . J . R . MacLeod. 13 X 19 cm. ; fip. xa 367. New York: John ‘CVileyand Sons, 1907. Price: $2.00 net.-This is a much less important book than that of Holleman and it is unfortunately a much less satisfactory one. After reading the book, one begins to wonder why the student should not learn some physical chemistry before he takes up organic chemistry. The chapter on molecular weight determinations, the theory of solutions, and the properties of colloids is not a structural part of the book and is not even accurate. On p. 45 the authors say that “the amount of this lowering, or depresston of the freezing-point, is proportional, not, in general, to the chemical nature of the substance, but to the number of molecules of substance dissolved in a given volume.” The same error occurs on the next page in a more explicit form. “An interesting explanation of the fact that C is quite different for different solvents is furnished in Raoult’s extension of his law: if a gram-molecule of a compound be dissolved in IOO gram-molecules of solvent (except water), the freezing-point of the latter will be depressed by about 0.02O.” On p. 54 is the unsupported statement “that the essential feature of colloidal solutions is the large size of the molecules or aggregates of molecules. These are especially large in hydrogels, but they may be broken up into smaller aggregates by warming; hence a hydrosolgel becomes a hydrosol by the aid of heat.”

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The following quotations will illustrate certain peculiarities in the point of view. On p. 58 the authors say: “We see then that the structural formula is not only a graphical expression of the actual.number of the various atoms in a molecule of the substance, but it is also an epitome of the more important reactions of the substance.” This is putting the cart before the horse in great style. The unfortunate student is likely to have trouble with the first paragraph on p. 60. “Before attempting to study the various organic substances individually, i t is essential that we possess a general idea of their relationship to one another. Their number is so great that, did we attempt to remember the properties and reactions of each organic substance separately, we should utterly fail, and *odd, moreover probably overlook one of their most important characteristics in contrast with inorganic substances, viz., their transmutability into other organic compounds. I n inorganic chemistry it is impossible to convert the compounds of one element into those of another element, except by substituting the elements. Each element has its own fixed chemical properties and compounds. I n organic chemistry, on the other hand, as remembered above, we may consider all our substances as compounds of the element carbon and as being, therefore, convertible into one another.” Wilder D. Bancroft. Feste LBsungen und Isomorphismus. B y Giuseppe Bruni. 14 X 22 cm; vi -k 130. Leipzig: A kadeniische Verlagsgesellschaft, m. b. H., 1908. Price:. paper, 4 marks; boumd, 5 marks.-In the autumn of 1907 Professor Bruni delivered a lecture on solid solutions before the Chemical Society of Breslau. This volume is based on that lecture, though much amplified and provided with a wealth of explanatory foot-notes. The first thirty pages deal with the general characteristics of solid solutions. Then come seventeen pages on crystalline form and chemical constitution, which are followed by thirty pages on crystalline form and the formation of solid solutions. As the reviewer has so often remarked, monographs of this type are much needed and we cannot have too many of them provided they are well written. This particular one is a satisfactory one. The author has played a n important part in the development of the subject; he has been on the right side in the disputed questions; and he presents his subject in a clear and orderly manner. I n one point the author goes a little further than our knowledge quite justifies. When speaking of solid solutions having a maximum melting-point, p. 3 1 , the author inclines to the belief that we are dealing with actual compounds and he remarks that “we are thus led to assume a kind of intermediate thing between a compound and a solution.” I t would have been much better to have pointed out frankly that w e cannot a t present distinguish between the hypothetical cases of two components forming a continuous series of solid solutions and of two components each forming a continuous series of solid solutions with a compound. This would have been the more desirable because people are continually telling us what are the constituents of a series of solid solutions even though there is often no evidence whatsoever in favor of their statements. Copper and zinc form six series of solid solutions; but there is no way at present of telling whether these different series of solid solutions are due to imaginary allotropic forms of copper and zinc, to unknown hypothetical compounds, or

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t o some other cause. I n the copper tin alloys we have a definite compound Cu,Sn which differs in all its known properties from the particular solid solution which has the same analytical composition. The author points out, p. 43, that isomorphism originally referred only t o cases in which two substances have similar constitution and similar crystalline form. Many chemists now use the term a s connoting the power to form solid solutions. Since these two requirements do not necessarily hold simultaneously, the author proposes the term “isogonism” instead of isomorphism as used by Mitscherlich and “synmorphism” to denote that two substances crystallize together. The word isomorphism would seem to drop out entirely under this arrangement. That would be distinctly undesirable and probably is not what the author intends. It was desirable, however, to lay stress on the loose way in which the word “isomorphism” is now used. It is much to be hoped that chemists and mineralogists can get together and decide on a fairly strict definition of the word. Wilder D . Bancroff. Quantitative Analyse durch Elektrolyse. B y Alexander Classen. (Fiilzjte Auflage i n durchaus neuer Bearbeitung). 14 X 21 cm; p p . xii + 336. Berlin : Julius Springer, ~goB.-About one-third of the book is taken up with a n introduction which seems superfluous because most people who will use the book do not need it while those who do need i t can find it more accurately elsewhere. On p. I O it is stated that a current which would precipitate 107.93 g. of silver from a silver nitrate solution would precipitate 18.63 g. of iron from ferric chloride solution. The fact is quite overlooked that iron does not precipitate from a ferric chloride solution. On p. 3 1 , the author overlooks the formation of cuprous chloride in the electrolysis of cupric chloride solutions. On p. 65, the author says that there is still much in regard to the theory of rapid precipitation which needs explanation; but there is nothing to show what these alleged difficulties are. On p. 55 it is misleading to say that too ’ rapid a precipitation of metal leads to a bad deposit. If the composition of the solution a t the cathode is kept constant, the experimental evidence is all t o the effect that there is no appreciable electrolytic time-factor. On p. 87 it is difficult to make anything out of the statements in regard to the evolution of hydrogen and nowhere in the book has the reviewer been able to find any statement as to the importance of hydrpgen evolution in connection with the electrolytic separation of two metals. These errors and omissions are merely the result of carelessness or ignorance. A more serious matter is the clever and consistent way in which the author treats the work done elsewhere, and especially that done a t the University of Pennsylvania. It is true that the other work is cited; but it is cited in such a way to give a n absolutely inaccura t e impression of the real development. Page 1 1 1 may be taken a s a n instance of what is meant, though page 65 is not much better since no reference is made to page VI of the preface. The working part of the book is satisfactory, though it suffers by comparison with E. F. Smith’s book. Besides the sections on determinations and separations, there is also a section dealing with the analysis of such things a s commercial copper, copper matte, bronzes, bearing metals, iron ore and steel, Wilder D . Bancroft. chrome nickel steel, manganese silicide, etc.

New Books Elektrochemie, 11. Experimentelle Elektrochemie, Messmethoden, Leitfahigkeit, Losungen. (Sammlung Goschera, N o . 253). B y Heinrich Danneel. I O X 15 cm; pp. 158. Leipzig: G. j . Goschen’ sche Verlagshuadlung, 1908. Price: bound, 80 pfennigs.--This second volume contains chapters on electrochemical measurements, the conductivity of electrolytes, and the electrochemistry of solutions. When one considers the small size of the pages, one is forced to admit that the book is a marvel of compactness. The author’s remarks on the conductivity of non-aqueous solutions, p. 87, and on the dissociating power of solvents, p. 93, are worth reading as unusually fair statements of the facts. Wilder D . Bancroft. Josiah Willard Gibbs a propos de la Publication de ses Mimozres Scientifiques. B y P, Duhem. 16 X 25 cm; pp. 43. Paris: A . Hermann, 1908. Price: paper, 2 francs.-In this brief sketch Duhem lays especial stress on the two points that Gibbs was essentially an algebraist and that “his mind was of a retiring disposition.” The following paragraphs give an excellent idea of certain aspects of Gibbs’s work. “Gibbs liked to contemplate truth, not in the variable and changing multiplicity of particular propositions but in the fixed and immovable unity of the general proposition. His thought did not try to reach out, even into wider developments of its consequences, but concentrated itself on the effort after a more abstract statement of the principles. This tendency characterizes the customary course of his genius. We have just recognized it in the method which he followed in announcing the results of his theories; we shall find it again, not less clearly marked, in the form to which he has given to the hypotheses from which these theories were devised.”. . . . “When the New Haven professor develops a physical theory, the hypotheses on which he bases his theory are always brought to the highest degree of generality while being reduced in number to a minimum. Sometimes a slightly greater restriction on these hypotheses would enable the imagination to help out the mind in its effort to grasp them; sometimes the citation of a.particular case would serve as an illustration of the general case and would help one to understand the latter. Gibbs never consents to impose such restrictions and he never condescends to give such examples.” While discussing the development of the phase rule by van der Waals and Roozeboom, Duhem writes: “M. Le Chatelier said with truth that Gibbs, by enunciating the phase rule, had done chemistry a service comparable to that which Lavoisier had rendered by formulating the law of the conservation of mass; but our legitimate admiration for the mathematician of New Haven, who wrapped the precious kernel in the hard rind of his algebraical formulas, should not interfere with our gratitude to the two Dutch chemists who crushed the ore and brought the pure metal to the sight of all. “M. van der Waals showed a remarkable perspicacity in discovering the phase rule among the algebraical formulas where Gibbs had, so to speak, hidden it. This same perspicacity came to the aid of the learned Dutch physicist on another occasion. When he undertook to study the laws which govern the liquefaction of a mixture of two gases, it was from the famous memoir of the

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Yale professor that he took the conception of the critical state of such a mixture. Since t h a t time the physicists of Leiden and of Amsterdam have been busied with the study of the surface corresponding to one of the functions defined in that memoir, the function “But though M. van der Waals was clear-sighted enough to discover some of the ideas which were present as germs in the equations of Gibbs, and though he had the skill to make them produce the experimental discoveries which were latent in them, how many similar seeds have remained sterile because no physicist and no chemist perceived them under the algebraical covering which hid them: The fruitfulness with which they were endowed has been recognized too late when the discoveries which should have resulted from them had already been made without reference to them.” Wilder D . Bancroft.

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Guide de Praparations Organiques a E’ Usage des gtudiants. B y Emil Fischer. Traduction autorisie d’afirks la sefitikme kdition allemande, par H . Decker et G. Duaant. 12 X 19 cm; fifi. xvii + I I O . Paris: Gauthier-Villars, 1907. Price: fiafier, 2.50 francs.-Since the German edition of this book is well known in this country, the special interest about the French edition lies in.the following remarks made by the translators in the preface: “Of late years there has been a movement against the use of laboratory manuals. I t often happened that students made all the preparations in a mechanical manner without concerning themselves with the literature and without taking the trouble to observe the phenomena which occurred during the course of the experiment. We find that manuals which give theoretical details, have the fault of not making the student find for himself the explanation of the preparations he has made, either in the works on organic chemistry or in the original literature. Other manuals go to the other extreme, giving only easy preparations, involving neither theoretical interest nor a methodical gradation in the experimental difficulties. I n view of the great development in laboratory teaching, the use of a manual has become necessary. I t represents a great economy of time and of labor for the assistant and permits him, by this fact alone, to direct his efforts towards the development of a certain manual dexterity and of the power of observation so essential to a chemist.” Wilder D . Bancroft. Handbuch der anorganischen Chemie. Herausgegebelz van R. A begg und Fr. Auerbach. I n vier BCLnden, zweiter Band, erste Abteilung: Die Elemente der ersten Grupfie des fieriodischen Systems; 18x25 cm; fib. xiii + 867. Leifizig: S. Hirzel, 1908. Price: fiafier, 24 marks; linen, 26 marks.-In this portly volume we have the subheads: hydrogen (Baur); lithium (Auerbach and Brislee); sodium (Hinrichsen) ; potassium (Hinrichsen) ; colloidal chemistry of the alkali metals (Lottermoser) ; rubidium (Hinrichsen) ; caesium (Hinrichsen) ; copper (Donnan) ; colloidal chemistry of copper (Lottermoser and Donnan) ; silver (Baur) ; colloidal chemistry of silver (Lottermoser) ; gold (Wohlwill) ; colloidal chemistry of gold (Lottermoser); while Brauner has charge of the sections on atomic weight determinations. The volume is an excellent one, the sections on copper and on the colloidal metals be’ing exceptionally good. Throughout the book Brauner takes the stand that the atomic weight determinations of Stas are inaccurate and that the values obtained by Richards

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and his pupils are the closest approximations to the real values which we have, This seems a reasonable attitude. We know of certain errors in Stas’s determinations. Of course he may have made other errors which we do not know about and which may have just counterbalanced the errors we know about; but this is very improbable indeed. On the other hand, there may be errors in the work of Richards which we do not yet recognize. This is quite conceivable and should make us cautious in talking about probable error, However this may be, there is no question but that the work of Richards is by far the most accurate that we have. In order to keep in touch with the international atomic weight commission, Brauner gives two sets of atomic weights, one based on Ag = 107.930, the other on Ag = 107,883. The first set he calls the ‘ancient’ values and the second the ‘modern’ values. Among the good features of the book are the discussions: of excess voltage, p. 86; of the equilibrium between copper, cupric salt and cuprous salt, p. 477; of the corrosion of copper, p. 559; of the oxidizing and catalytic action of copper salts, p. 569; and of the copper-iron equilibrium, p. 5 7 2 . Anybody who is interested in such things will do well to compare the section on cuprous hydroxide, p. 583, with the corresponding one in Dammer’s Handbuch. The chapters on the chloride, bromide, and iodide of silver are as satisfactory as one can expect in view of our shocking ignorance in regard to these salts, I n the article on sodium, the reviewer found a few statements with which he could not sympathize. On p. 209 the author says that sodium is made commercially, chiefly b y the electrolytic processes of Castner, Grabau, and Borchers. Two paragraphs are then given to the commercial production of sodium by electrolysis of fused sodium chloride. No one could possibly guess from this that Castner’s process is the only commercial one and that no sodium is made commercially by the electrolysis of fused sodium chloride. On p. 217 is the statement that we cannot determine the dissociation of strong electrolytes from conductivity measurements because the values thus obtained do not accord with Ostmald’s dilution law. On p. 298 i t is stated that the Solvay process for making sodium carbonate is now being superseded by tlie electrolytic process (presumably Hargreaves and Bird). The reviewer knows no facts which justify such a statement. Wzlder. D. Bancroft. The Chemistry of the Diazo-Compounds. B y John Cawell Cam. 14 x Pfi. x 172. London: Edward Arnold. New 170rk: Longmans, Green Er’ Co., 1908. Price: $3 00 net.-This is a much-needed monograph, The question of the constitution of the diazo compounds is one over which organic chemists have fought for many years with ever-changing views. A summarized statement of our knowledge in regard to these compounds is therefore much to be desired and this we now have. The author has been handicapped a little b y trying to do two different things, to give the chemistry of the diazo compounds and to sketch the development of the constitution formulas, While the author has given us a very interestinq account of the conflict between Hantzsch and Bamberger, i t must be admitted that the narrative is a bit jerky and disconnected in places. This may perhaps be due in part to the fact that the author does not agree with either side and is waiting a chance to bring in his own theory, which he does in a n appendix, His view is that in the diazo 22 cni;

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salts we have a quinonoid configuration of the diazo-salts and “that a n atom of nitrogen in these salts is attached t o the aromatic nucleus by two linkings.” Wilder D. Bancroft.

Les DBcouvertes Modernes en Physique. Leur Thdorie et leur R81e d a m 1’Hypothkse de la Constitution &lectrique de la hlatikre. B y 0. Alanville. 14 x zz c m ; pp. ai 186. Paris: A . Hermann, 1908. Price: paper, 5 jrancs.The author feels that the electronic theory of matter has not received the attention in France that i t should, chiefly because of the lack of a suitable book on the subject. It is the praiseworthy object of the author to dispel these clouds of ignorance. The treatise under consideration ‘contains seven chapters: electrical discharge through liquids; discharge through gases; ionization of gases; electrons; introduction to the electronic theory of matter; induced radio-activity; the electronic theory of matter. The first chapter deals with the electrolytic dissociation theory. The author ascribes to Arrhenius the famous saying that electrolytes are salts. H e considers that the ions are the elements existing in the solutions with free affinities. A necessary consequence of this is that the ions must polymerize when they are set free. This presents no difficulty with hydrogen and chlorine. Some people might have difficulties with copper; but the author states boldly that metallic copper is a solid polymer of the copper ion. Incidentally, the author gives the Greek words from which ion, anion, cation, anode and cathode are derived; but either his Greek is faulty or his proof-reading because the accents are wrong on every one of the words involved, As a rule, the author does not mis-spell foreign names with that grace which usually characterizes French writers, though it must be admitted that Hittdorf and Towsend are pretty successful efforts in this line, It is possible that the author’s book will have the desired effect upon his countrymen. If so, he will have been successful even beyond his deserts. W’ilder D. Bancroft.

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Radioaktive Umwandlungen. B y E. Rutherford. Ubevsetzt von M . Levin. (Die T I ’issemchaft. Sammlung naturwissenschaftlicher und mathematischer Moiaoqraphien. Heft 21.) 14 x 21 c m ; p p . via, 285. Braunschweig: Friedrich Vieweq und Sohn, 1907. Price: paper, 8.00 marks; linen, 8.60 marks.The English version has already been reviewed (11, 423). I t is a pleasure to note the appearance of a German translation. IT‘ilder D. Bancroft.

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Fliissige Kristalle und die Theorien des Lebens. B y 0. Lehmann. Zweite durch Zusalze verbesserte duflaqe. 13 Y 20 c m ; pp. 69. Leipzig: Johania A m brosius Barth, 1908. Price: linen, 1.,50 marks.-The first’ edition of this little book appeared in 1906 and was reviewed (11, 640). One interesting feature of the new edition is the quotation on p. 68 of several of the reviews of the first edition from which it appears that there is great difference of opinion as to what the author’s view-point really is. The author himself says that while he is striving toward the artificial production of living organisms, he does not assume that such a result is necessarily possible. H e is trying to find out whether there are reasons which make such a result impossible and, if so, what they are. bVilder D. Bancroft.