Practical Organic Chemistry, изд. 3

Автор(ы):Vogel I.
06.10.2007
Год изд.:1956
Издание:3
Описание: The favourable reception accorded to previous editions by reviewers, students and practising organic chemists has encouraged the author to undertake an exhaustive revision of the entire text in the light of the numerous developments in practical organic chemistry since the book was first written (1945-46). The net result has been an increase in the length of the volume by some 150 pages, a figure which gives some indication of the new matter incorporated in the present edition.
Оглавление:
Practical Organic Chemistry — обложка книги. Обложка книги.
CHAPTER I THEORY OF GENERAL TECHNIQUE
  THEORY OF DISTILLATION
    I.1. Vapour pressure [1]
    I.2. Calculation of the boiling point at selected pressures [2]
    I.3. Superheating and bumping [3]
    I.4. Fractional distillation [5]
    I.5. The breaking up of azeotropic mixtures [12]
    I.6. Steam distillation. Distillation of a pair of immiscible liquids [12]
    I.7. Distillation with superheated steam [15]
  SOLUTIONS OF LIQUIDS IN LIQUIDS
    I.8. Partially miscible liquids. Critical solution temperature [17]
    I.9. Influence of added substances upon the critical solution temperature [20]
  THEORY OF MELTING AND FREEZING
    I.10. Melting point and vapour pressure  [21]
    I.11. Effect of impurities upon the melting point [23]
    I.12. System in which the solid phases consist of the pure components and the components are completely miscible in the liquid phase [24]
    I.13. Construction of equilibrium diagrams [26]
    I.14. System in which the two components form a compound possessing a congruent melting point [29]
    I.15. System in which the two components form a compound with an incongruent melting point [31]
    I.16. System in which the two components form a continuous series of solid solutions [32]
    I.17. Mixed melting points [34]
    I.18. System in which the solid phases consist of the pure components and the components are only partially miscible in the liquid state [35]
    I.19. Theory of sublimation [37]
    I.20. Theory of the action of drying agents [39]
    I.21. Deliquescence and efflorescence [43]
    I.22. Extraction with solvents [44]
CHAPTER II EXPERIMENTAL TECHNIQUE
    II.1. Common laboratory apparatus [46]
    II.2. Cleaning and drying of glassware [53]
    II.3. Use of cork and rubber stoppers [55]
    II.4. Cutting and bending of glass tubing [57]
    II.5. Heating baths [57]
    II.6. Cooling baths [60]
    II.7. Mechanical agitation [62]
    II.8. Gas absorption traps [71]
    II.9. Calibration of thermometers [72]
    II.10. Experimental determination of the melting point [75]
    II.11. Miscellaneous forms of melting point apparatus [80]
    II.12. Experimental determination of the boiling point [83]
    II.13. Typical assemblies of apparatus for distillation and refluxing [86]
    II.14. Fire hazards attending the distillation of inflammable solvents [90]
    II.15. Fractional distillation. Distillation with a fractionating column [91]
    II.16. Simple apparatus for fractionation [93]
    II.17. Improved apparatus for fractional distillation [94]
    II.18. Still heads for fractionating columns [102]
    II.19. Distillation under diminished pressure (" vacuum " distillation) [103]
    II.20. Fractional distillation under diminished pressure [108]
    II.21. Water pumps [110]
    II.22. Oil pumps [110]
    II.23. Manometers and manostats [112]
    II.24. Refinements in the technique of distillation under diminished pressure [116]
    II.25. Precision fractional distillation under diminished pressure [119]
    II.26. Molecular distillation [120]
    II.27. Purification of solid organic compounds by crystallisation. General considerations [122]
    II.28. Experimental details for recrystallisation [125]
    II.29. Preparation of a fluted filter paper [127]
    II.30. Removal of traces of colouring matter and resinous products. Use of decolourising carbon [127]
    II.31. Difficulties encountered in recrystallisation [129]
    II.32. Filtration with suction [130]
    II.33. Drying of the recrystallised material [132]
    II.34. Filtration of small quantities of material with suction [133]
    II.35. Miscellaneous apparatus for filtration with suction [133]
    II.36. Recrystallisation in an atmosphere of inert gas [135]
    II.37. Evaporation of the solvent [135]
    II.38. Drying of solid organic compounds [136]
    II.39. Drying of liquids or of solutions of organic compounds in organic solvents [139]
    II.40. Technique of steam distillation [145]
    II.41. Modifications of the steam distillation apparatus [146]
    II.42. Technique of extraction with solvents [149]
    II.43. Extraction by chemically active solvents [151]
    II.44. Continuous extraction of liquids or solids by solvents [152]
    II.45. Technique of sublimation [154]
    II.46. Chromatographic adsorption [156]
    II.47. Purification of the common organic solvents [163]
    II.48. Inorganic reagents—gases [179]
    II.49. Inorganic reagents—liquids [186]
    II.50. Inorganic reagents—solids [190]
    II.51. Calculation of yields [201]
    II.52. General instructions for work in the laboratory [204]
    II.53. Safety precautions [205]
  APPARATUS WITH INTERCHANGEABLE GROUND GLASS JOINTS
    II.54. Interchangeable ground glass joints [206]
    II.55. Types of ground glass joints [210]
    II.56. Apparatus with interchangeable ground glass joints suitable lor general use ш preparative organic chemistry [212]
    II.57. Electric heating mantles (lor use in fractional distillation, etc.) [221]
    II.58. Apparatus for the continuous extraction of solids or liquids by solvents [222]
    II.59. Lubrication of ground glass joints [225]
    II.60. Typical assemblies [226]
CHAPTER III PREPARATION AND REACTIONS OF ALIPHATIC COMPOUNDS
  PRELIMINARY LABORATORY OPERATIONS
    III.1. Determination of melting points [229]
    III.2. Mixed melting points [229]
    III.3. Determination of boiling points [230]
    III.4. Fractional distillation [231]
    III.5. Purification of solid organic compounds by recrystallisation [232]
  SATURATED ALIPHATIC HYDROCARBONS
    III.6. Reactions and characterisation of saturated aliphatic hydrocarbons [234]
    III.7. n-Octane (Wurtz reaction) [236]
    III.8. n-Hexuiie (hydrocarbon from Orignard reagent) [237]
    III.9. n-Octane (Clemmensen reduction oj a ketone) [238]
  ETHYLENIC HYDROCARBONS (ALKENES)
    III.10. Ainylene [239]
    III.11. Reactions and characterisation of ethylenic hydrocarbons [241]
    III.12. cycloHexene [243]
  ACETYLENIC HYDROCARBONS (ALKYNES)
    III.13. Acetylene [245]
  ALIPHATIC ALCOHOLS [247]
    III.14. n-Amyl alcohol (from ethyl n-valerate) [249]
    III.15. Tetramethylene glycol (1:4-butanediol) [250]
    III.16. n-Heptyl alcohol (froni n-heptaldehyde) [251]
    III.17. cycloHexylcarbinol (from cyclohexyl chloride) [252]
    III.18. n-Hexyl alcohol (from n-butyl bromide) [253]
    III.19. n-Nonyl alcohol (from n-heptyl bromide) [254]
    III.20. Methyl n-amyl carbinol (from methyl n-amyl ketone) [254]
    III.21. Methyl n-butyl carbinol (from methyl n-butyl ketone) [255]
    III.22. Methyl iso-propyl carbinol [255]
    III.23. Di-n-butyl carbinol (from n-butyl bromide) [256]
    III.24. Dimethyl n-butyl Carbinol [257]
    III.25. Triethyl carbinol [258]
    III.26. Dimethyl n-propyl carbinol [259]
    III.27. Reactions and characterisation of aliphatic alcohols [260]
  ALKYL HALIDES [270]
    III.28. n-Butyl chloride (ZnCl(?)-HCl method) [272]
    III.29. sec.-Butyl chloride (ZnCl(?)-HCl method) [273]
    III.30. iso-Butyl chloride (SOCl(?)-Pyridine method) [274]
    III.31. n-Hexyl chloride (SOCl(?), method) [274]
    III.32. cycloHexyl chloride (HCl - CaCl(?) method) [275]
    III.33. tert.-Butyl cliloride (HCl method) [276]
    III.34. isoPropyl bromide (HBr method) [277]
    III.35. n-Butyl bromide (HBr-H(?)SO(?) method) [277]
    III.36. n-Butyl bromide (KBr-H(?)SO(?) method) [280]
    III.37. n-Butyl bromide (red P Вr(?) method) [281]
    III.38. 1:4-Diiodobutane (KI-H(?)PO(?) method) [284]
    III.39. isoPropyl iodide (HI method) [285]
    III.40. n-Butyl iodide (red P and I(?) method) [285]
    III.41. n-Hexyl fluoride [288]
    III.42. Reactions and characterisation of alkyl halides [289]
  POLYHALOGEN COMPOUNDS [297]
    III.43. Chloroform [297]
    III.44. Bromoform [299]
    III.45. lodoform [299]
    III.46. Methylene bromide [300]
    III.47. Methylene iodide [300]
    III.48. 1:2:3-Tribromopropane [301]
  ESTERS OF INORGANIC ACIDS [302]
    III.49. w-Butyl sulphite [303]
    III.50. n-Butyl phosphate [304]
    III.51. n-Butyl borate [304]
    III.52. n-Propyl thiocyanate [305]
    III.53. n-Amyl nitrite [306]
    III.54. 1-Nitro-n-butane (AgNO(?) method) [307]
    III.55. Nitromethane [307]
  ALIPHATIC ETHERS [309]
    III.56. Diethyl ether [310]
    III.57. Di-n-butyl ether [311]
    III.58. Ethyl n-hexyl ether [313]
    III.59. cycloHexyl ethyl ether [314]
    III.60. Reactions and characterisation of aliphatic ethers [315]
  ALIPHATIC ALDEHYDES [318]
    III.61. n-Butyraldehyde [320]
    III.62. n-Hexaldehyde (catalyst method) [321]
    III.63. n-Hexaldehyde (ethyl orthoformate method) [323]
    III.64. n-Hexaldehyde (from n-amyl cyanide) [324]
    III.65. Acetaldehyde (from paraldehyde) [324]
    III.66. Formaldehyde [325]
    III.67. Hexamethylenetetramine (hexamine) [326]
    III.68. Acetal (acetaldehyde diethylacetal) [327]
    III.69. Reactions and characterisation of acetals [327]
    III.70. Reactions and characterisation of aliphatic aldehydes [330]
  ALIPHATIC KETONER [335]
    III.71. Methyl n-hexyl ketone [336]
    III.72. Diethyl ketone [338]
    III.73. cycloPentanone [340]
    III.74. Reactions and characterisation of aliphatic ketones [341]
    III.75. Acetone cyanohydrin [348]
    III.76. n-Heptaldoxime [348]
    III.77. Pinacol and pinacolone [349]
    III.78. Diacetone alcohol [351]
    III.79. Mesityl oxide [353]
  SATURATED ALIPHATIC MONOBASIC ACIDS [354]
    III.80. iso-Butyric acid [355]
    III.81. n-Heptoic acid [356]
    III.82. n-Butyl n-butyrate [357]
    III.83. n-Valeric acid (hydrolysis of n-butyl cyanide) [357]
    III.84. dZ-Methylethylacetic acid (carbonation of a Grignard reagent) [358]
    III.85. Reactions and characterisation of aliphatic carboxylic acids [360]
  ACID CHLORIDES OF ALIPHATIC CARBOXYLIC ACIDS [367]
    III.86. Acetyl chloride [367]
    III.87. n-Butyryl chloride [368]
    III.88. Reactions and characterisation of acid chlorides of aliphatic acids [369]
  ACID ANHYDRIDES OF ALIPHATIC CARBOXYLIC ACIDS [371]
    III.89. Acetic anhydride [372]
    III.90. Keten [372]
    III.91. n-Caproic anhydride [374]
    III.92. Succinic anhydride [375]
    III.93. Maleic anhydride [376]
    III.94. Reactions and characterisation of acid anhydrides (aliphatic) [376]
  ALIPHATIC ESTERS [379]
    III.95. n-Butyl acetate [382]
    III.96. tert.-Butyl acetate [383]
    III.97. n-Butyl formate [384]
    III.98. cycloHexyl acetate [385]
    III.99. Diethyl adipate (azeotropic mixture method) [385]
    III.100. Diethyl adipate (benzene method) [386]
    III.101. n-Propyl n-valerate [387]
    III.102. iso-Propyl lactate (ton exchange resin catalyst method) [387]
    III.103. Diethyl maleate (silver salt method) [388]
    III.104. Ethyl n-valerate (from n-butyl cyanide) [389]
    III.105. Ethyl vinylacetate (acid chloride method) [389]
    III.106. Reactions and characterisation of aliphatic esters [390]
  ALIPHATIC AMIDES [401]
    III.107. Acetamide (from ammonium acetate or from acetic acid) [401]
    III.108. Acetamide (from ethyl acetate) [403]
    III.109. n-Caproamide [404]
    III.110. Reactions and characterisation of aliphatic amides [404]
  ALIPHATIC CYANIDES (NITRILES) [407]
    III.111. Acetonitrile [407]
    III.112. n-Amyl cyanide (n-capronitrile) [408]
    III.113. n-Butyl cyanide (n-valeronitrile) [408]
    III.114. Trimethylene dicyanide (glutaronitrile) [409]
    III.115. Reactions and characterisation of aliphatic cyanides (nitriles) [410]
  ALIPHATIC AMINES [413]
    III.116. Methylamine hydrochloride (from acetamide) [414]
    III.117. Methylamme hydrochloride (from formalin) [415]
    III.118. Dimethylamine hydrochloride [416]
    III.119. Trimethylamine hydrochloride [416]
    III.120. n-Amylamine [417]
    III.121. n-Heptylamine [418]
    III.122. Di-n-butylamine [419]
    III.123. Reactions and characterisation of aliphatic amines [420]
    III.124. N-Nitrosodimethylamine (dimethylnitrosamine) [426]
  SUBSTITUTED ALIPHATIC MONOBASIC ACIDS [427]
    III.125. Monochloroacetic acid [428]
    III.126. Monobromoacetic acid and ethyl bromoacetate [429]
    III.127. Dichloroacetie acid [431]
    III.128. Trichloroacetic acid [431]
    III.129. Glycine (aminoacetic acid) [432]
    III.130. (?)-Amino-n-caproic acid (norleucine) [432]
    III.131. Ethyl cyanoacetate [433]
    III.132. Reactions and characterisation of ammo acirls [435]
    III.133. Urea [441]
    III.134. Thiourea (thiocarbamide) [442]
  POLYHYDRIC ALCOHOLS, FATS AND SOAPS [444]
    III.135. Saponification of a fat. Soap [445]
    III.136. Reactions and characterisation of polyhydric alcohols [446]
  CARBOHYDRATES [449]
    III.137. (?)- and (?)-Glucose penta-acetate [451]
    III.138. Mucic acid [452]
    III.139. Reactions and characterisation of carbohydrates [453]
      Photographs of osazones [455]
  UNSATURATED ALIPHATIC COMPOUNDS
    III.140. Allyl alcohol [459]
    III.141. Crotonaldehyde [460]
    III.142. (?)-Dimethylacrylic acid [460]
    III.143. Maleic and fumaric acids [461]
    III.144. Crotonic acid and vinylacetic acid [463]
    III.145. Sorbic acid [466]
    III.146. Diallyl (hexadiene-1,5) [466]
    III.147. 2:3-Dimethyl-1: 3-butadierie [467]
    III.148. Dimethylethynyl carbinol [467]
    III.149. 10-Undecynoic acid [468]
    III.150. Catalytic reduction with Adams' platinum oxide catalyst [470]
  ETHYL ACETOACETATE [475]
    III.151. Ethyl acetoacetate [477]
    III.152. Ethyl n-propylacetoacetate and methyl n-butyl ketono [481]
  DIETHYL MALONATE [483]
    III.153. Diethyl malonate [484]
    III.154. Ethyl n-butylmalonato [485]
    III.155. n-Caproic acid (from ethyl n-butylmalonate) [486]
    III.156. n-Propylmalonic acid [488]
  SOME ALIPHATIC DICARBOXYLIC ACIDS [489]
    III.157. Malonic acid [490]
    III.158. Glutaric acid (from trimethylene dicyanide) [491]
    III.159. Pimelic acid (from benzoyl piperidine) [492]
    III.160. Glutaric acid (Jrom cyclopentanone) [493]
    III.161. Adipic acid [494]
    III.162. as-Dimethylsuccinic acid [495]
  ALIPHATIC SULPHUR COMPOUNDS [496]
    III.163. n-Hoxyl mercaptan (n-hexyl thiol) [497]
    III.164. Di-n-propyl sulphide [497]
    III.165. Diethyl disulphide [498]
    III.166. Potassium ethyl xanthate [499]
    III.167. Ethyl S-ethyl xanthate [499]
    III.168. Reactions and characterisation of mercaptans (thiols) [500]
  RESOLUTION OF A RACEMIC COMPOUND
    III.169. Determination of the rotatory power [503]
    III.170. Resolution of sec.-octyl alcohol (dl-2-octanol) into its optically active components (d- and l-2-octanol) [506]
CHAPTER IV PREPARATION AND REACTIONS OF AROMATIC COMPOUNDS AROMATIC HYDROCARBONS [508]
    IV.1. n-Butylbenaene (Wurtz -Fittig synthesis) [511]
    IV.2. iso-Propylbenzene (cumene) [512]
    IV.3. tert.-Butylbcnzene [613]
    IV.4. Diphenylmethane [613]
    IV.5. Triphenylmethane [615]
    IV.6. Ethylbenzene [615]
    IV.7. n-Propylbenzene [616]
    IV.8. n-Amylbenzene [517]
    IV.9. Characterisation of aromatic hydrocarbons [518]
  NITRATION OF AROMATIC HYDROCARBONS [523]
    IV.10. Nitrobenzene [525]
    IV.11. (?)-Nitronaphthalene [526]
    IV.12. m-Dinitrobenzene [526]
    IV.13. 2:4-Dinitrotoluene [527]
    IV.14. (?)-Bromonitrobenzene [527]
    IV.15. 2:2'-Dmitrodiphenyl [527]
    IV.16A. Reactions and characterisation of aromatic nitre compounds [528]
    IV.16B. Reactions and characterisation of aliphatic nitro compounds [531]
  HALOGENATION OF AROMATIC HYDROCARBONS [533]
    IV.17. Chlorobenzene [535]
    IV.18. Bromobenzene [536]
    IV.19. m-Bromonitrobonzene [537]
    IV.20. (?)-Bromonaphthalene [537]
    IV.21. lodobenzene [538]
    IV.22. Benzyl chloride (cfdorination of toluene) [538]
    IV.23. Benzyl chloride (Moromethylation of benzene) [539]
    IV.24. lodobenzene dichloride [541]
    IV.25. lodosobenzene [541]
    IV.26. lodoxybenzene [542]
    IV.27. Diphenyliodonium iodide [542]
    IV.28. Reactions and characterisation of halogenated aromatic hydro carbons [542]
  SULPHONATION OF AROMATIC HYDROCARBONS [548]
    IV.29. Sodium benzenesulphonate [549]
    IV.30. Sodium (?)-toluenesulphonate [550]
    IV.31. Sodium (?)-naphthalenesulphonate [551]
    IV.32. (?)-Toluenesulphonic acid [552]
    IV.33. Reactions and characterisation of aromatic sulphonic acids [552]
    IV.33A. Reactions and characterisation of aromatic sulphonamides [558]
  AROMATIC AMINES AND THEIR SIMPLE DERIVATIVES [559]
    IV.34. Aniline [563]
    IV.35. (?)-Phenylethylamine [566]
    IV.36. (?)-Phenylethylamine [567]
    IV.37. (?)-Naphthylamine [568]
    IV.38. (?)-Naphthylamine [568]
    IV.39. Benzylamine (Qabriel synthesie) [569]
    IV.40. Pure methylaniline from commercial methylaniline [570]
    IV.41. Benzylaniline [572]
    IV.42. Dimethylaniline [572]
    IV.43. p-Nitrosodimethylaniline [573]
    IV.44. m-Nitroaniline [574]
  ACETYLATION OF AROMATIC AMINES [576]
    IV.45. Acetanilide [577]
    IV.46. Diacetyl-o-toluidiue [578]
    IV.47. 2:4:6-Tribromoacetanilide [579]
    IV.48. p-Bromoacetanilide [580]
    IV.49. p-Bromoaniline [580]
    IV.50. p-Nitroacetanilide [581]
    IV.51. p-Nitroaniline [581]
  BENZOYLATION OF AROMATIC AMINES [582]
    IV.52. Benzanilide (Schotten - Baumann reaction) [582]
    IV.53. Benzanilide [583]
    IV.54. Hippurio acid (benzoyl glycine) [584]
  SULPHONATION OF AROMATIC AMINES [585]
    IV.55. Sulphanilic acid [586]
    IV.56. Naphthionic acid [586]
    IV.57. Orthanilic acid [587]
    IV.58. Metanilic acid [589]
  DIAZONIUM SALTS [690]
    IV.59. Solid phenyldiazonium chloride [597]
    IV.60. Icxlobenzene [598]
    IV.61. p-Chlorotoluene [600]
    IV.62. p-Bromotoluene (Sandmeyer reaction) [602]
    IV.63. m-Bromotoluene [605]
    IV.64. o-Bromotoluene (Gattermann reaction) [606]
    IV.65. Beiizenesulphinic acid [607]
    IV.66. p-Tolunitrile (p-tolyl cyanide) [607]
    IV.67. Fluorobenzene [609]
    IV.68. o-Dinitrobenzene [612]
    IV.69. Phenol (from aniline) [613]
    IV.70. m-Nitrophenol [614]
    IV.71. Toluene (/ram p-toluidine) [616]
    IV.72. sym.-Tribromobenzene [615]
    IV.73. 3:3'-Dimethyldiphenyl [616]
    IV.74. Diphenic acid (from anthranilic acid) [617]
    IV.75. Phenylarsonic acid [617]
  SOME AZO DYESTUFFS [620]
    IV.76. Phenyl-azo-p-naphthol [622]
    IV.77. Chrysoidine [623]
    IV.78. Mothyl orange [624]
    IV.79. Orange II ((?)-naphthol orange) [625]
    IV.80. Methyl red [625]
    IV.81. Diazoaminobenzene [626]
    IV.82. p-Amino-azobenzene [627]
  INTERMEDIATE PRODUCTS IN THE REDUCTION OF NITRO COMPOUNDS [628]
    IV.83. (?)-Phenylhydroxylamine [629]
    IV.84. Nitrosobenzene [630]
    IV.85. Azoxybenzene [631]
    IV.86. Azobeiizene [631]
    IV.87. Hydrazobenzene (sym.-diphenylhydrazine) [632]
    IV.88. Benzidine [633]
  REDUCTION OF DIAZONIUM COMPOUNDS. ARYL HYDRAZINES [635]
    IV.89. Phenylhydrazine [636]
    IV.90. p-Nitrophenylhydrazine [637]
    IV.91. 2:4-Dinitrophenylhydrazine [638]
  AROMATIC DIAMINES [640]
    IV.92. o-Plienylenediamine [640]
    IV.93. m-Phenylenediamine [641]
  MISCELLANEOUS COMPOUNDS DERIVED FROM PRIMARY AMINES
    IV.94. Tliioearbanilide (sym.-diphenylthiourea) [642]
    IV.95. Phenyl iso-thiocyanate (from thiocarbanilide) [642]
    IV.96. Phenyl iso-thiocyanate (from aniline) [643]
    IV.97. Phenylurea (cyanate method) [644]
    IV.98. Phenylurea (urea method) [645]
    IV.99. p-Iodoaniline [647]
    IV.100. Reactions and characterisation of aromatic amines [648]
  PHENOLS [664]
    IV.101. p-Cresol [667]
    IV.102. (?)-Naphthol [668]
    IV.103. Phenyl acetate [669]
    IV.104. Anisole [669]
    IV.105. Phenyl n-butyl ether [671]
    IV.106. Reactions and characterisation of aromatic ethers [671]
    IV.107. o-Propiophenol and p-propiophenol [676]
    IV.108. o-and p-nitrophenols [677]
    IV.109. 2:4-Dinitrophenol [678]
    IV.110. Picric acid (2:4:6-trinitrophenol) [678]
    IV.111. p-Bromophenol [679]
    IV.112. o-Bromophenol [679]
    IV.113. p-Iodophenol [680]
    IV.114. Reactions and characterisation of phenols [681]
  AROMATIC ALDEHYDES [689]
    IV.115. Benzaldehyde [693]
    IV.116. p-Broniobenzaldehyde [694]
    IV.117. p-Nibrobenzaldehyde [695]
    IV.118. p-Tolualdehyde [697]
    IV.119. (?)-Naphthaldehyde [698]
    IV.120. (?)-Naphthaldehyde (Sommelet reaction) [700]
    IV.121. Mesitaldehyde [701]
    IV.122. Salicylaldehyde [703]
  CONDENSATION REACTIONS OF AROMATIC ALDEHYDES [706]
    IV.123. Benzyl alcohol and benzoic acid (Cannizzaro reaction) [711]
    IV.124. Cinnamic acid [712]
    IV.125. Benzoin [714]
    IV.126. Benzil [714]
    IV.127. Benzilic acid [716]
    IV.128. Benzalacetone [716]
    IV.129. (?)-Nitrostyrene [717]
    IV.130. Benzalacetophenone (chalcone) [718]
    IV.131. Ethyl cinnamate [718]
    IV.132. (?)-Piperonylacrylic acid (3:4-methylenedioxycinnamic acid) [719]
    IV.133. (?)- and (?)-Benzaldoxiines [719]
    IV.134. Hydrobenzamide [720]
    IV.135. Reactions and characterisation of aromatic aldehydes [720]
  AROMATIC KETONES [725]
    IV.136. Acetophenone [729]
    IV.137. Butyrophenone [732]
    IV.138. p-Bromoacetophenone [732]
    IV.139. Benzophenone [733]
    IV.140. Benzylacetophenono [734]
    IV.141. Methyl benzyl ketone [734]
    IV.142. Phloroacetophenone [736]
    IV.143. (?)-Tetralone [737]
    IV.144. o-Benzoylbenzoic acid [739]
    IV.145. Anthraquinone [740]
    IV.146. Anthrone [740]
    IV.147. Benzophenone oxiine and Beckmann rearrangement [741]
    IV.148. Reactions and characterisation of aromatic ketones [741]
  QUINONES [745]
    IV.149. p-Benzoquinone ("quinone ") [745]
    IV.150. 1:2-Naphthoquinone [746]
    IV.151. Quinhydrone [747]
    IV.152. Reactions and characterisation of quinones [747]
  AROMATIC CARBOXYLIC ACIDS [751]
    IV.153. Benzole acid [755]
    IV.154. p-Nitrobenzoic acid [757]
    IV.155. 2:4:6-Trinitrobenzoic acid [758]
    IV.156. 2:4-Dinitrophenylacetic acid [758]
    IV.157. o-Chlorobenzoic acid [768]
    IV.158. Terephthalic acid [760]
    IV.159. o-Toluicacid [760]
    IV.160. Phenylacetic acid (from benzyl cyanide) [761]
    IV.161. p-Nitrophenylacetic acid [763]
    IV.162. p-Aminophenylacetic acid [764]
    IV.163. (?)-Naphthoic acid [764]
    IV.164. (?)-Naphthoic acid [766]
    IV.165. Diphenic acid (from pheuuntltrKne) [768]
    IV.166. Hydrocinnamic acid [768]
    IV.167. m-Nitrobenzoic acid [769]
    IV.168. 3:5-Dinitrobenzoic acid [770]
    IV.169. Homophthalic acid [771]
    IV.170. Anthranilie acid [773]
    IV.171. Diphonylacetic acid [773]
    IV.172. Mandelic acid [774]
    IV.173. Salicylic acid [774]
    IV.174. Phenylpropiolic acid [776]
    IV.175. Reactions and characterisation of aromatic carboxylic acids [777]
  AROMATIC ESTERS [780]
    IV.176. Methyl benzoate [781]
    IV.177. Methyl salicylate [782]
    IV.178. Benzyl acetate [783]
    IV.179. Ethyl phenylacetate [783]
    IV.180. Phenyl einnamate [784]
    IV.181. Phenyl benzoate [784]
    IV.182. Ethyl (?)-naphthoate [785]
    IV.183. Reactions and characterisation of aromatic esters [785]
  AROMATIC ACID CHLORIDES [791]
    IV.184. p-Nitrobenzoyl chloride [791]
    IV.185. Benzoyl chloride [792]
  AROMATIC ACID ANHYDRIDES [794]
    IV.186. p-Chlorobenzoic anhydride [794]
    IV.187. Reactions and characterisation of acid chlorides of aromatic acids [795]
  AROMATIC ACID AMIDES [797]
    IV.188. Benzamide [797]
    IV.189. Mercury benzamide [797]
    IV.190. o-Toluamide [798]
    IV.191. Reactions and characterisation of primary aromatic amides [798]
    IV.192. Reactions and characterisation of substituted aromatic amides (aromatic acylated bases) [801]
  AROMATIC NITRILES [803]
    IV.193. Benzonitrile [803]
    IV.194. Veratronitrile [804]
    IV.195. Keactions and characterisation of aromatic nitriles [805]
  SOME AROMATIC PEROXIDES AND PER-ACTDS [807]
    IV.196. Benzoyl peroxide [807]
    IV.197. p-Nitrobenzoyl peroxide [808]
    IV.198. Perbenzoic acid (benzoyl hydrogen peroxide) [808]
    IV.199. Monoperphthalic acid [810]
  AROMATIC ALCOHOLS [811]
    IV.200. p-Tolyl carbinol (p-methyl benzyl alcohol) [812]
    IV.201. Benzhydrol (diphenylcarbinol) [812]
    IV.202. Triphenylcarbinol [813]
    IV.203. Triphenylchloromethane [815]
    IV.204. (?)-Phenylethyl alcohol [816]
    IV.205. Reactions and characterisation of aromatic alcohols [817]
  COMPOUNDS DERIVED FROM AROMATIC SULPHONIC ACIDS [820]
    IV.206. Benzenesulphonyl chloride [822]
    IV.207. p-Toluenesulphonyl chloride [822]
    IV.208. Dichloramine-T and chloramine-T [823]
    IV.209. Saccharin [824]
    IV.210. n-Butyl p-toluenesulphonate [825]
    IV.211. Sodium p-toluenesulphinate [826]
    IV.212. Thiophenol [827]
CHAPTER V SOME HETEROCYCLIC AND ALICYCLIC COMPOUNDS
    V.1. Quinoline [829]
    V.2. Quinaldine [831]
    V.3. Furfuryl alcohol and furoic acid [832]
    V.4. 2-Furfuralacetone [833]
    V.5. Furylacrylic acid [834]
    V.6. Furoin [835]
    V.7. Furil [835]
    V.8. 2-Methylthiophene [836]
    V.9. 2:5-Dimethylthiophene [836]
    V.10. 2-Acetylthiophene [837]
    V.11. Pyrrole [837]
    V.12. 2:5-Dimethylpyrrole [838]
    V.13. 2:4-Dimethyl-3: 5-dicarbethoxypyrrole [839]
    V.14. Succinimide [840]
    V.15. 2-Aminothiazole [840]
    V.16. 2:4-Dimethylthiazole [841]
    V.17. 2:5-Dimethylpyrazole [842]
    V.18. 5:5-Dimethylhydantoin [843]
    V.19. 4-Ethylpyridine(from pyridine) [844]
    V.20. n-Amylpyridines (from picolines) [845]
    V.21. Picolinic acid [847]
    V.22. Nicotinie acid [848]
    V.23. Ethyl nicotinate [849]
    V.24. (?)-Cyanopyridine [850]
    V.25. Uramil [850]
    V.26. 2-Phenylindole [851]
    V.27. Benzimidazole [853]
    V.28. 4-Methylcoumarin [853]
    V.29. 2-Hydroxy]epidine (4-methylcarbostyril) [855]
    V.30. Phenylbenzoyldiazomethane [856]
    V.31. 2-Carbethoxycyclopentanone [856]
    V.32. cycloButane-1 : 1-dicarboxylic 'acid and cyclobutanecnrboxylic acid [857]
    V.33. cycloPropanecarboxylic acid [859]
CHAPTER VI MISCELLANEOUS REACTIONS
    VI.1. Acetylacetone [861]
    VI.2. Benzoylacetone [865]
    VI.3. Phenylglyoxal [866]
    VI.4. Apparatus for reactions under pressure [866]
    VI.5. Raney nickel (catalyst) [870]
    VI.6. Copper - chromium oxide catalyst [872]
    VI.7. Hexamethylene glycol (1:6-Hexanediol) [873]
    VI.8. Ethyl (?)-phenyl-(?)-hydroxypropionate [874]
    VI.9. (?)-Dimethylglutaric acid [876]
    VI.10. Reductions with lithium aluminium hydride [877]
    VI.11. Reductions with potassium (or sodium) borohydride [881]
    VI.12. Reductions with aluminium alkoxides [882]
    VI.13. The Oppeiiauor oxidation [886]
    VI.14. Oxidation of unsaturated compounds with ozonized oxygen (ozonolysis) [888]
    VI.15. Epoxidation and hydroxylation of ethylenic compounds [893]
    VI.16. Reactions in liquid ammonia. Some acetylenic compounds [895]
    VI.17. The Arndt-Eistert reaction [902]
    VI.18. The Darzens glycidic ester condensation [906]
    VI.19. The Brlenmeyer azlactone reaction [907]
    VI.20. The Mannich reaction [910]
    VI.21. The Michael reaction [912]
    VI.22. Cyanoethylation [914]
    VI.23. The Schmidt reaction or rearrangement [917]
    VI.24. The Stobbe condensation [919]
    VI.25. The Willgerodt reaction [923]
    VI.26. The Wohl-Ziegler reaction. Applications of N-bromosuccinimide [926]
    VI.27. Synthesis of unsymmetrical diaryls [927]
    VI.28. Syntheses with organolithium compounds [928]
    VI.29. Syntheses with organosodium compounds [933]
    VI.30. Syntheses with organocadmium compounds [935]
    VI.31. Some electrolytic syntheses [937]
    VI.32. The diene synthesis (Diels-Alder reaction) [941]
    VI.33. Some applications of chromatographic adsorption [944]
    VI.34. Ring enlargement with diazomethane. cycloHeptanone from cyclohexanone [946]
    VI.35. Dehydrogenation of hydroaromatic compounds [947]
    VI.36. Preparation of palladium catalysts for hydrogenation [949]
    VI.37. Oxidation with lead tetra-acetate. n-Butyl glyoxylate [961]
СНАРТЕЕ VII ORGANIC REAGENTS IN INORGANIC AND ORGANIC CHEMISTRY    
    VII.1. Dimethylglyoxime [953]
    VII.2. Semicarbazide hydroehloride [954]
    VII.3. Diphenylcarbazide [954]
    VII.4. Diphenylcarbazone [955]
    VII.5. Dithizone (diphenylthiocarbnzone) [955]
    VII.6. Cupferron [957]
    VII.7. Salicylaldoxime [957]
    VII.8. (?)-Benzomoxime [958]
    VII.9. (?)-Nitroso-(?)-naphthol [958]
    VII.10. Ammonium salt of aurin tricarboxylic acid ("aluminon") [959]
    VII.11. p-Nitrobenzene-azo-(?)-naphthol [960]
    VII.12. p-Bromophenacyl bromide [960]
    VII.13. p-Nitrobenzyl bromide [961]
    VII.14. p-Phenylphenacyl bromide [962]
    VII.15. 5:5-Dimethyl-1:3-cyclohexanedione (dimethyldihydro-rosorcinol) [963]
    VII.16. Xanthhydrol [964]
    VII.17. 1:3:5-Trmitrobenzene [965]
    VII.18. S-Benzyl-iso-thiuroniuiii chloride [965]
    VII.19. 3-Nitrophthalic anhydride [966]
    VII.20. Diazomethane [967]
    VII.21. 3:4:5-Triiodobenzoyl chloride [973]
    VII.22. 3:5-Dinitrobenzoyl chloride [974]
    VII.23. 1:2-cycloHexanedione-dioxime (nioxime) [974]
    VII.24. Quinaldinic acid [975]
    VII.25. Girard's reagents "Т" and "P" [976]
    VII.26. Pseudo-saccharin chloride [978]
CHAPTER VIII DYESTUFFS, INDICATORS AND RELATED COMPOUNDS        
    VIII.1. Congo red  [979]
    VIII.2. Indigo [980]
    VIII.3. Alizarin [981]
    VIII.4. Crystal violet [982]
    VIII.5. Copper phthalocyanine (Monastral Blue) [983]
    VIII.6. Phenolphthalein [984]
    VIII.7. Fluorescein and eosin [985]
    VIII.8. pp -Tetramethyldiammodiphenylmethane [987]
    VIII.9. o-Sulphobenzoic anhydride [987]
    VIII.10. Sulphonephthaloins [989]
    VIII.11. N-Phenylanthranilic acid [991]
    VIII.12. 1:10-Phenanthroline [991]
    VIII.13. 2:2'-Dipyridyl [992]
    VIII.14 Ninhydrin (indane-1:2:3-trione hydrate) [993]
CHAPTER IX SOME PHYSIOLOGICALLY ACTIVE COMPOUNDS
    IX.1. Aspirin (acetylsalicylic acid) [996]
    IX.2. Phenacetin [996]
    IX.3. Antipyrine [998]
    IX.4. Bromural ((?)-bromo-iso-valerylurea) [999]
    IX.5. Benzocaine (ethyl p-aminobenzoate) [1000]
    IX.6. Barbituric acid [1001]
    IХ.7. Diethylbarbituric acid (veronal) [1002]
    IX.8. Phenylethylbarbituric acid (phenobarbitone) [1003]
    IX.9. p-Aminobenzenesulphonamide (sulphanilamide) [1005]
    IX.10. 2-(p-Aminobenzenesulphonamido) pyridine (sulphapyridine) [1007]
    IX.11. Sulphaguanidine [1009]
    IX.12. 2-Phenylquinoline-4-carboxylic acid (atophan) [1010]
    IX.13. 2:2-bis(;p-Chlorophenyl)-1:1:1-trichloroethane (D.D.T.) [1011]
    IX.14. 3-Indoleacetic acid [1012]
CHAPTER X SYNTHETIC POLYMERS
    X.1. Brief introduction to subject [1014]
    X.2. Phenol-formaldehyde resin [1022]
    X.3. Depolymerisation of methyl methacrylate resin [1023]
    X.4. Formation of a glyptal resin [1023]
    X.5. Thiokol A (polyethylene polysulphide) [1024]
    X.6. Phenylethylene (styrene) [1024]
    X.7. Polystyrene [1025]
    X.8. Ethylenediamine - adipic acid polymer [1026]
    X.9. Depolymerisation of a hexamethylenediamine - adipic acid polymer (Nylon "66") [1026]
CHAPTER XI QUALITATIVE ORGANIC ANALYSIS
    XI.1. Basis of qualitative organic analysis [1026]
    XI.2. Determination of physical constants [1028]
    XI.3. Qualitative analysis for the elements [1038]
    XI.4. The solubilities of organic compounds [1046]
    XI.5. The solubility groups [1050]
    XI.6. Determination of the solubilities of organic compounds (for group tests) [1065]
    XI.7. Class reactions (reactions for functional groups) [1057]
    XI.8. The preparation of derivatives [1081]
    XI.9. Qualitative analysis of mixtures of organic compounds [1090]
CHAPTER XII SEMIMICRO TECHNIQUE
    XII.1. Introduction and general considerations [1101]
    XII.2. Some typical operations on the semimicro scale [1102]
    XII.3. Semimicro apparatus with interchangeable ground glass joints [1109]
    XII.4. Small-scale preparations [1110]
APPENDIX
  LITERATURE OF ORGANIC CHEMISTRY
    A.1. Beilstein's "Handbuch" [1115]
    A.2. Original sources of chemical information [1127]
    A.3. Secondary sources of chemical information. Abstracting journals [1127]
    A.4. Locating an organic compound [1128]
    A.5. Selected reference works on organic chemistry [1128]
    A.6. Laboratory accidents and first aid [1130]
    A.7. Applications of infrared and ultraviolet spectra to organic chemistry [1134]
    A.8. Densities and percentage compositions of various solutions [1151]
    A.9. Density and vapour pressure of water: 0° to 35° C [1162]
    A.10. Atomic weights [1163]
INDEX [1165]
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