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148] ALIPHATIC COMPOUNDS 46? the remainder of the allyl iodide in small portions over a period of 2 hours. Allow the mixture to cool during 3 hours and arrange the flask for distillation (compare Fig. 11,13, 3). Distil from an oil or butyl phthalate bath maintained at 90-100° when most of the hydrocarbon will pass over ; finally raise the temperature of the bath to 150° in order to recover the product as completely as possible. The distillate weighs 26 g. and is almost pure diallyl. Redistil from a 50 ml. Claisen flask with fractionating side arm and containing a little sodium ; all the liquid boils at 59-60°. 111,147. 2 : 3-DIMETHYL-l : 3-BUTADIENE Anhydrous pinacol (I) is catalytically decomposed by aqueous hydrobromic acid into dimethylbutadiene (II) and pinacolone (III) ; separation is effected by distillation through an efficient fractionating column : OH I CH3—C—CH3 HBr CM 3—C=CHo 2 I (I) — I *(II)+(CH,),C-COCH, (III) CH3—C—CH3 CH3—C=CH2 In a 1-litre round-bottomed flask, surmounted by a modified Hempel fractionating column (Fig. //, 25, 5) filled with £" or \" glass or porcelain rings (1), place 177 g. of anhydrous pinacol (Section 111,77), 5 ml. of constant boiling point hydrobromic acid, and a few fragments of porous porcelain. Attach a condenser and a receiver to the column. Heat the flask gently in an air bath (compare Fig. II, 5, 3) and circulate cold water through the " cold finger " : the rate of distillation should be 20-30 drops per minute. Collect the distillate until the temperature at the top of the column is 95° (60-70 minutes). Separate the upper non-aqueous layer, wash it twice with 50 ml. portions of water, add 0-25 g. of hydroquinone as an inhibitor, and dry it overnight with 7-8 g. of anhydrous calcium chloride. Transfer to a 500 ml. flask and distil through the same column (or through a Widmer column). Collect the following fractions : (a) 69-70-5° (70 g.), (6) 70-5-105° (7 g.), and (c) 105-106° (35 g.). Fraction (a) is pure dimethylbutadiene, (6) is an intermediate fraction and (c) is pinacolone. Dimethylbutadiene may be kept for a limited period in an ice box or in a refrigerator ; it is advisable to add about 0-2 g. of hydroquinone as an inhibitor. Note. (1) Any efficient fractionating column may be used (see Section II, 17). 111,148. DIMETHYLETHYNYL CARBINOL This is an example of an acetylenic alcohol. It is prepared from acetone by the following series of reactions : CH3COCH3 + NaNH2 —* (CH3COCH2)Na + NH3 (CH3COCH2)Na + C2H2 —• (CH3)2C(C^CH)ONa (CH^qC^CHjONa+HjSO, —• (CHs)2C(OH)—C=CH +NaHS04
468 PRACTICAL ORGANIC CHEMISTRY [HI. Fit a 1-litre round-bottomed flask with a three-holed stopper carrying a separatory funnel, a mechanical stirrer and a gas outlet tube leading to a fume cupboard. Place 500 ml. of anhydrous ether and 78 g. of finely-ground sodamide (Section 11,5 0,
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A TEXT-BOOK OF P R A C T I C A L O
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PREFACE TO THIRD EDITION THE favour
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PREFACE TO FIRST EDITION vn the new
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CONTENTS CHAPTER I THEORY OF GENERA
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CONTENTS xiii PAGE 11.58. Apparatus
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CONTENTS xv PAGE 111.76. n-Heptaldo
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CONTENTS xvii PAGE SOME ALIPHATIC D
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CONTENTS xix PAGE DIAZONIUM SALTS 5
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CONTENTS xxi PAGE QUINONES 745 IV,1
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CONTENTS XX1J1 PAGE V,20. n-Amylpyr
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CONTENTS XXV PAGE 1X,7. Diethylbarb
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NAME INDEX OF ORGANIC REACTIONS xxv
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2 PRACTICAL ORGANIC CHEMISTRY [I. e
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4 PRACTICAL ORGANIC CHEMISTRY [I. b
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6 PRACTICAL ORGANIC CHEMISTRY [I. L
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8 PRACTICAL ORGANIC CHEMISTRY [I. r
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10 PRACTICAL ORGANIC CHEMISTRY P. L
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12 PRACTICAL ORGANIC CHEMISTRY [!
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24 PRACTICAL ORGANIC CHEMISTRY [I,
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34 PRACTICAL ORGANIC CHEMISTRY [1.
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CHAPTER IT EXPERIMENTAL TECHNIQUE 1
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48 PRACTICAL ORGANIC CHEMISTRY [II.
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50 PRACTICAL ORGANIC CHEMISTRY PL h
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52 PRACTICAL ORGANIC CHEMISTRY [II,
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64 PRACTICAL ORGANIC CHEMISTRY III.
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66 PRACTICAL ORGANIC CHEMISTRY [H.
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u PRACTICAL ORGANIC CHEMISTRY [II,
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M PRACTICAL ORGANIC CHEMISTRY [II.
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90 PRACTICAL ORGANIC CHEMISTRY [H,
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96 rRACTICAL ORGANIC CHEMISTRY [II,
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102 PRACTICAL ORGANIC CHEMISTRY [II
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11% PRACTICAL ORGANIC CHEMISTRY PL
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114 PRACTICAL ORGANIC CHEMISTRY rn,
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122 PRACTICAL ORGANIC CHEMISTRY [IL
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138 PRACTICAL ORGANIC CHEMISTRY PL
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156 PRACTICAL ORGANIC CHEMISTRY [M.
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172 PRACTICAL ORGANIC CHEMISTRY [«
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176 PRACTICAL ORGANIC CHEMISTRY in.
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206 PRACTICAL ORGANIC CHEMISTRY [">
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228 PRACTICAL ORGANIC CHEMISTRY [11
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234 PRACTICAL ORGANIC CHEMISTRY [HI
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246 PRACTICAL ORGANIC CHEMISTRY [IU
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250 PRACTICAL ORGANIC CHExMISTRY [H
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252 PRACTICAL ORGANIC CHEMISTRY fil
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TABLE 111,27. Alcohol Diacetone alc
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TABLE 111,42, Halide ALIPHATIO HALO
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TABLE 111,42. ALIPHATIC HALOGEN COM
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TABLE 111,70. Formaldehyde Aldehyde
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344 PRACTICAL ORGANIC CHEMISTRY [Hi
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TABLE III, 74. ALIPHATIC KETONES Ke
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TABLE 111,85. ALIPHATIC CARBOXYLIC
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394 PRACTICAL ORGANIC CHEMISTRY I H
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396 PRACTICAL ORGANIC CHEMISTRY TAB
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412 PRACTICAL ORGANIC CHEMISTRY [in
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518 PRACTICAL ORGANIC CHEMISTRY [IV
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TABLE IV,9. Hydrocarbon Diphenyl .
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552 PRACTICAL ORGANIC CHEMISTRY [VI
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562 PRACTICAL ORGANIC CHEMISTRY (IV
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TABLE IV,100A. Amine Aniline . o-To
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TABLE IV,100A. PRIMARY AROMATIC AMI
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TABLE IV,114. PHENOLS (continued) P
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TABLE IV,U4A. ENOLS Compound Acetyl
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702 PRACTICAL ORGANIC CHEMISTRY LIV
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TABLE IV,205. Alcohol Benzyl P-Phen
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CHAPTER V SOME HETEROCYCLIC AND ALI
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830 PRACTICAL ORGANIC CHEMISTRY [V,
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CHAPTER X SYNTHETIC POLYMERS X,l. B
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1016 PRACTICAL ORGANIC CHEMISTRY [X
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CHAPTER XI QUALITATIVE ORGANIC ANAL
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TABLE A,8,2. 1 PER CENT. CH8OH BY 1
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TABLE A,8,5. AQUEOUS NITRIC ACID PE
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TABLE A,8,9. PER CENT. HBr BY WEIGH
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TABLE kfi,12. AQUEOUS AMMONIA SOLUT
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TABLE A,8,/6. AQUEOUS POTASSIUM CAR
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A,9. DENSITY AND VAPOUR PRESSURE OF
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INDEX Page numbers in bold-faced ty
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a-Amino-n caproic acid, 427, 432 4-
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a-Benzilmonoxime, 720 P-Benzilmonox
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m-Chlorobenzoic acid, 929, 932 o-Ch
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Diethylaniline, 562, 573 purificati
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p-Ethylbenzyl chloride, 540 Ethyl b
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Halogen carriers, 533 Halogen compo
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Magnesium sulphate, as desiccant, 4
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m-Nitroaniline, 563, 574 7>-Nitroan
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a-Picoline, purification of, 177 p-
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Semimicro apparatus—cord, distill
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Thermometers, 72 calibration curve
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