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L a B O R a T O R Y M E T H O D S of O R G a N I C C H E M I S T R Y LABORATORY METHODS OF ORGANIC CHEMISTRY BY L. GATTERMANN COMPLETELY REVISED BY HEINRICH WIELAND TRANSLATED FROM THE TWENTY-FOURTH GERMAN EDITION BY W. MCCARTNEY, PH.D.(EDIN.), A.I.C. LATE ASSISTANT IN THE DEPARTMENT OF MEDICAL CHEMISTRY, UNIVERSITY OF EDINBURGH WITH 59 ILLUSTRATIONS IN THE TEXT NEW YORK THE MACMILLAN COMPANY 1937 COPYRIGHT PRINTFD IN GEEAT BRITAIN BY R. & R. CLARK, LIMITED, EDINBUEGH PEEFACE TO THE TWENTY-FOUKTH EDITION WHILE the student is being educated in preparative work it is necessary for him to acquire some knowledge of the incessant pro- gress in the methods of organic chemistry and at the same time to become familiar with the most recent results of research work. For these reasons a series of changes had to be made when this new edition was prepared. In order not to increase the bulk of the book these objects have been attained by sacrificing examples (e.g. lino- lenic acid, crystal violet, Gattermann-Koch aldehyde synthesis) with which, from this point of view, it seemed possible to dispense. Of the newly included methods two may be mentioned here : analysis by chromatographic adsorption which has attained such great importance, and the ozonisation of unsaturated compounds by the recently well-developed procedure. The section on analytical methods has been completely re- written because the development of organic chemistry has caused the macro-methods practised in the classic period, methods which required considerable amount of material, to come to be regarded as survivals. The candidate for the Doctor degree, we know, no longer has to acquire the art of carrying out combustions since he is rightly unwilling, in practising this art, to sacrifice relatively enormous amounts of pure substance, often laboriously obtained. On various grounds I doubt the advisability of including micro-analysis in general practical courses. During a period of two years we have obtained such good results in this laboratory with a procedure worked out, on the basis of Pregl's method, by Dr. F. Holscher that I have included it in this book. For this procedure 20-30 mg. of substance are required. The position has been reached where the candidate for the Doctor vi LABORATOKY METHODS OF ORGANIC CHEMISTRY degree who reaps from his investigation a harvest not altogether too scanty and too precious, again carries out himself the com- bustion of his substances. It will be understood that, in working out this " meso-analytical " method now recommended we have made use, not only of the funda- mental principles of Pregl, but also of all practical and tested improvements of other authors. (I propose the term " meso- analytical " instead of the clumsy " half-micro ".) A reprint of the English edition of the book has appeared, and I have by chance learned that it has been translated into Russian and already published in two very large editions in Soviet Russia. An Italian translation is in course of preparation. I again have to thank several colleagues for valuable suggestions. In particular I have to thank Prof. F. G. Fischer, Freiburg, and Dr. Elisabeth Dane, as well as my teaching assistant Dr. G. Hesse, for their active collaboration in the revision of the book. The proofs have been corrected by T. Wieland. HEINRICH WIELAND MUNICH, June 1935 PEEFACE TO THE EEVISED (NINETEENTH) EDITION IT is rather more than thirty years ago since Ludwig Gattermann published the first edition of his Anleitungfiir das organisch-chemische Praktikum. The plan of providing the preparative directions with theoretical explanations has certainly proved satisfactory. That is already shown by the wide circulation of the book, of which eighteen editions have appeared. Methodology and technique are undoubtedly the chief objects of the practical course, but aiming merely at culinary art and technical achievement such a course does not accomplish enough. A command of methods implies above all an understanding of their rationale and a power of adapting their numerous modifications to particular requirements; the architect is more important than the mason. We demand that the student should be conversant with the theory of the transfor- mations which he carries out practically. The comments made on the individual preparations are intended to facilitate a survey of the subject in hand, and to encourage the use of text-books and journals by further reading. Now that a knowledge of the principles of organic chemistry may be assumed during the pre- parative work in German universities, the danger of such com- ments becoming a pons asinorum is remote. In rewriting the book the theoretical and practical requirements have been deliberately increased. The equipment which sufficed during the last three decades has now become insufficient for those who desire to work at present-day problems, where difficulties have been accentuated alike in pure science and in technology. The idea of making the preparative work at once an explanation and a living experience of the science has demanded a rearrange- viii LABOKATOKY METHODS OF ORGANIC CHBMISTEY ment of the subject matter in accordance with systematic relation- ships. It will be seen that the new arrangement does not depart seriously from the path which ascends from the more simple to the more difficult. In any case a considerable educational advantage may be expected to result from the rounding off of successive sub- jects. The general part as well as the analytical have been completely revised and greatly shortened in order to make more space for the preparative part. The increase in the number of preparations is intended to provide variety, and to counteract a tendency towards stereotyped routine in the organic practical course. I am greatly indebted to my assistants, especially to Drs. Franz Bergel and F. Gottwalt Fischer, for untiring co-operation in carrying out numerous experiments. Dr. Fischer has, moreover, drawn the new diagrams for this edition and has prepared the index. HBINEICH WIBLAND FEEIBURG I. B., Master 1925 CONTENTS A. SOME GENERAL LABORATORY RULES PAGE Reaction Velocity and Temperature ...... 1 Purification of Organic Substances ...... 3 Crystallisation ........ 4 Chromatographic adsorption ...... 14 Distillation ......... 15 Sublimation ......... 26 Distillation with Steam ....... 27 Evaporation of Solvents ....... 29 Extraction ......... 32 Working with Compressed Gases . .35 Heating under Pressure ....... 37 Stirring and Shaking ........ 38 Determination of the Melting Point ...... 40 B. ORGANIC ANALYTICAL METHODS Detection of Carbon, Hydrogen, Nitrogen, Sulphur, and the Halogens . 43 Organic Elementary Analysis ...... 46 I. Determination of Nitrogen by Dumas' Method . .47 II. Determination of Carbon and Hydrogen by Liebig's Method . 55 III. Determination of Halogen, Sulphur, and other Elements . 69 1. Determination of halogen by the Carius method, p. 69; 2. Argentometric determination of chlorine and bromine, p. 73; 3. Iodine determination by the Leipert-Munster method, p. 76; 4. Determination of sulphur by the Carius method, p. 77; 5. Deter- mination of sulphur by combustion, p. 78; 6. Simultaneous determination of halogen and sulphur, p. 79; 7. Determination of other elements, p. 79. IV. Determination of Organic Groups . .80 1. Volumetric determination of methoxyl and ethoxyl, p. 80; 2. Determination of the acetyl and benzoyl groups, p. 82; 3. Determination of active hydrogen by the method of Tschugaeff and Zerevitinoff, p. 84. V. Determination of Molecular Weight . .86 x LABOKATOKY METHODS OF OEGANIC CHBMISTEY C. PREPARATIVE PART PAGE On the Prevention of Accidents ...... 88 Equipment required by the Beginner . .90 I. THE REPLACEMENT OF HYDROXYL AND HYDBOQEN BY HALOGEN. ALCOHOLS AND OLEITNES 1. Ethyl bromide from ethyl alcohol . .93 • Methyl bromide, p. 95. 2. Ethyl iodide from ethyl alcohol ...... 95 Methyl iodide, p. 96. 3. Benzyl chloride from toluene ...... 100 4. Bromobenzene ........ 103 2>-Dibromobenzene, p. 105. 5. Ethylene from ethyl alcohol. Ethylene dibromide . 107 6. Glycol from ethylene dibromide . .114 7. Isoamyl ether . .117 8. Chloroacetic acid from acetic acid and chlorine . .118 II. CAEBOXYLIC ACIDS AND THEIE SIMPLE DERIVATIVES 1. Acid chlorides ........ 121 (a) Acetyl chloride, p. 121 ; (b) Benzoyl chloride, p. 121 ; Acetanilide, p. 125 ; Benzoyl peroxide, p. 125. 2. Acetic anhydride . t. 126 3. Acetamide ......... 129 Benzamide, p. 130. 4. Urea and semicarbazide . .131 (a) Potassium cyanate by oxidative fusion, p. 131 ; (b) Urea, p. 132 ; (c) Semicarbazide, p. 134; (d) Urea (and uric acid) from urine, p. 135. 5. Nitriles 137 (a) Acetonitrile, p. 137 ; (b) Benzyl cyanide, p. 137. 6. Hydrolysis of a nitrile to the acid. Phenylacetic acid . 140 7. Esters 141 (a) Ethyl acetate from acetic acid and alcohol, p. 141, Ethyl benzoate, p. 141; (6) Isoamyl nitrite, p. 146, Ethyl nitrite, p. 147 ; (c) Ethyl nitrate, p. 148 ; (d) Hydrolysis of fat or vegetable oil, p. 149 ; Prepara- tion of the free fatty acid, p. 150, Glycerol, p. 150; Analysis of fats, p. 151. 8. Conversion of carboxylic acids into the next lower amines . .152 (a) The Hofmann reaction. Methylamine from acetamide, p. 152; (b) The Curtius reaction, p. 153, Benzoyl azide, p. 153, Phenyl cyanate, p. 153, Phenylurethane, p. 154. CONTENTS x III. NlTBO-COMPOUNDS AND THEIR REDUCTION PRODUCTS PAG] 1. Nitromethane . 15( Methylamine, p. 158, N-Methylhydroxylamine, p. 158, Methyl- nitrolio acid, p. 158, Silver fulminate, p. 159, Phenylnitroethylene, p. 160. 2. Nitration of an aromatic hydrocarbon . .161 (a) Nitrobenzene, p. 161; (b) Dinitrobenzene, p. 162. 3. Reduction of a nitro-compound to an amine .... 16£ (a) Aniline from nitrobenzene, p. 165, Diphenyltbiourea, Phenyl- isothiocyanate, p. 169; (b) m-Nitraniline from m-dinitrobenzene, p. 171. 4. Phenylhydroxylamine ....... 174 y-Aminophenol, p. 176, Nitrosophenylhydroxylamine, p. 177. 5. Nitrosobenzene . 17S Nitrosobenzene from aniline and Caro's acid, p. 179, Azobenzene from aniline and nitrosobenzene, p. 181, Azoxybenzene from phenyl- hydroxylamine and nitrosobenzene, p. 182. 6. Hydrazobenzene and azobenzene ...... 183 (a) Hydrazobenzene, p. 183; (b) Azobenzene from hydrazobenzene, p. 184; (c) Benzidine from hydrazobenzene, p. 186. Mechanism of the reduction of nitrobenzene, p.
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