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94] ALIPHATIC COMPOUNDS 377 derivative for the characterisation of an anhydride of a dibasic acid (particularly if it is a liquid) and indirectly for the dibasic acid itself. Dissolve 0*5 g. of succinic anhydride in 15 ml. of benzene by heating on a water bath, and add a solution of 0 • 5 ml. of aniline in 3 ml. of benzene. The anilic acid soon separates in a crystalline form.* Cool, filter off the crystals and wash with a little benzene. Recrystallise from dilute alcohol and determine the m.p. Pure suecinanilic acid (I) melts at 150° CH2COv CH2COOH | >0 + H2NC6H5 — | (I) CH2OT CH2CONHC6H5 The above simple experiments illustrate the more important properties of the anhydrides of aliphatic acids. For their characterisation, the reaction with aniline or ^-toluidine is frequently employed. Alternatively, the anhydride may be hydrolysed with dilute alkali as detailed under Acid Chlorides, Section 111,88, and the resulting acid characterised as in Section 111,85. The physical properties of a number of acid anhydrides (aliphatic) are given in Table 111,94. * If the anhydride of an unknown acid is being used and the anilic acid does not crystallise after the mixture has been boiled for a short time, cool the solution, wash it with dilute hydrochloric acid to remove the excess of aniline, and evaporate the solvent; the anilic acid will then usually crystallise.
378 PRACTICAL ORGANIC CHEMISTRY [HI. TABLE 111,94. ACID ANHYDRIDES J Anhydride Acetic . . . . Propionic . n-Butyric . t*o-Butyric. n-Valeric . wo-Valeric(p-Methyl-n-butyri n-Caproic (n-hexoic) . t>o-Caproic (wo-butylacetic) n-Heptoic (oenanthic) . n-Octoic (capric) Crotonic Succinic Glutaric Maleic Citraconic . Itaconic d-Camphoric Monochloroacetic Dichloroacetic Trichloroacetic . o) B.P 140° 166 198 182 218 215 245 139°/19 258 285 247 261 150 o /10 198 213 139730 270 109711 101716 223 (ALIPHATIC) M.P. — — — — — — — 17° — — 120 56 56 7 68 220 46 — — ,20° 1-081 1022 0-968 0-956 0-925 0-933 0-920 — 0-917 0-910 1040 — — — — — — — — D 1-390 1-404 1-413 — — 1-404 1-430 — 1-433 1-434 1-474 — — — — — — — —
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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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CHAPTER IT EXPERIMENTAL TECHNIQUE 1
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48 PRACTICAL ORGANIC CHEMISTRY [II.
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M PRACTICAL ORGANIC CHEMISTRY [II.
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96 rRACTICAL ORGANIC CHEMISTRY [II,
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114 PRACTICAL ORGANIC CHEMISTRY rn,
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122 PRACTICAL ORGANIC CHEMISTRY [IL
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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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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 111,132. AMINO ACIDS—Contin
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TABLE 111,136. POLYHYDRIC ALCOHOLS
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LACTOSAZONE MALTOSAZONE CELLOBIOSAZ
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CHAPTER IV AROMATIC COMPOUNDS AROMA
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510 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,100C. Amine p-Bromodimethy
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702 PRACTICAL ORGANIC CHEMISTRY LIV
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TABLE IV.175. Add Benzoic o-Toluic
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788 PRACTICAL ORGANIC CHEMISTRY TAB
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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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834 PRACTICAL ORGANIC CHEMISTRY [V.
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888 PRACTICAL ORGANIC CHEMISTRY IV1
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910 PRACTICAL ORGANIC CHEMISTRY IVI
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CHAPTER IX SOME PHYSIOLOGICALLY ACT
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1000 PRACTICAL ORGANIC CHEMISTRY [I
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1010 PRACTICAL ORGANIC CHEMISTRY fi
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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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1088 PRACTICAL ORGANIC CHEMISTRY TA
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1116 PRACTICAL ORGANIC CHEMISTRY [A
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TABLE A,8,2. 1 PER CENT. CH8OH BY 1
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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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