Laboratory Methods of Organic Chemistry - Sciencemadness Dot Org

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428 INDEX Anthraquinone 334 Anthrone 335 Antipyrine 297 Apparatus for beginners 90-91 Apparatus with standard ground joints 2 Araban 386 Arabinose 386 Arginine hydrochloride 404 Arsanilic acid 293, 294 Arsenobenzene 295 /8-Arylacrylic acids 233 Aryl disulphides 202 Arylpropionic acids 233 Ascorbic acid 400 Atophan 368 Atoxyl 295 Autocatalysis 148 Autoxidation of aldehydes 212 Auxochromic groups 180, 304 Avertin 222 Azibenzil 227 Azides 289 Azobenzene 181, 184, 312 Azo-components 305 Azo-dyes, analysis of, 301 Azomethane 275 Azomethines 167, 181 Azoxybenzene 182, 189 Babo's air bath 17 Baeyer's test 112 Bakelite 220, 243 Baking process 198 Bart's reaction 293, 295 Bases, tertiary, degradation with cyanogen bromide, 364 Bathychromic effect 248, 314 Beckmann rearrangement 344 Beer's law 354 Beilstein's test 45 Benzacetoin 223 Benzaldehyde 209 Benzamide 130 Benzanilide 344 Benzaurin 328 Benzene from aniline 285 from phenylhydrazine 299 Benzene hexachloride 106 Benzene ring, substitution in, 106, 163, 164, 173, 197-199, 237 Benzenesulphinic acid 193, 201 Benzene sulphohydroxamic acid 192 Benzenesulphonamide 192 Benzenesulphonic acid 191 Benzenesulphonyl chloride 192 Benzhydrazide 153 Benzidine 186 Benzidine dyes 302 Benzidine rearrangement 187 Benzil 222 Benzil dioximes 346 Benzil monoximes 346 Benzil osazone 223 Benzilic acid 225 rearrangement 225 Benzohydrol 337 Benzoic acid 220 Benzoic anhydride 126 Benzoin 222 Benzonitrile 292 Benzophenone 227, 343 Benzophenone oxime 344 Benzopyranole 268 BenzofHchloride 102 Benzoylacetone 253 Benzoylacetylacetone 263 Benzoylacetyl peroxide 213 Benzoyl azide 153 o-Benzoylbenzoic acid 351 Benzoyl chloride 121 Benzoyl, determination of, 82 Benzoyl peroxide 125 Benzyl alcohol 220 Benzylamine 102 Benzyl chloride 100 Benzyl cyanide 137 Benzylideneacetone 181 Benzylideneaniline 167 Benzylidene chloride 102 Benzylidene phenylhydrazone 297-298 Bindschedler's green 321 Bioses, constitution of, 397-398 Biphenyleneglycollic acid 225 Bis-diazoacetic acid 279 Bis-y-dimethylaminodiphenyl-nitrogen 359 Bismarck brown 172 Bitter almond oil 211 Bixin 233 - Boric acid, increasing its conductivity with sugars, 396 Borneol 226 Bredt's rule 226 Bromination 106, 119, 257, 261 Bromine titration of enols 261 Bromobenzene 103 /3-Bromopropionic acid 120 Bromotoluenes (o-, m-, p) 293 Biichner funnel 9, 10 Butadiene 113, 306 Butyric acid 255 Caffeine 405 Camphene 87, 226
Cannizzaro's reaction 220 Carbimide 139 Carbodiphenylimide 170 Carbohydrates 395-400 Carboligase 223 Carbonium salts 330, 355 Carbon suboxide 227 Carbyl sulphate 197 Cardiac poisons 416 Caro's acid, oxidation with, 179 Carotene 233 Carotenoids 233 Casein 391 hydrolysis of, 392 Catalytic hydrogenation 376-383, 385 Catechin 268 Cellobiose 395 Centrifuge 14 Cetyl iodide 98 Chlorauric acid 406 Chlorine, determination of, 69, 73, 103 carriers 119 Chloroacetic acid 118 o-Chlorobenzoic acid 106 Chloroiodoethylene 285 Chlorophyll 410, 411 Chloroplatinic acid 406 Cholanic acid 413, 415 Cholatrienic acid 413 Choleic acid 414 Cholesterol 415 Cholic acid 412 Choline 116 Chromanol 268 Chromatographic adsorption 14-15, 410.411 Chromophoric groups 304 Cinnamic acid 232 hydrogenation of, 234, 377-378 Citral 220 Claisen flask 20, 31 Clemmensen'a method of reduction 383 " Cold finger " 7 Collidine 362 Collidine dicarboxylic acid, ethyl ester, 360 Collidine dicarboxylic acid, potassium salt of, 362 Compressed gases 35-37 Concentration of reactants 3 Congo red 302 Conjugated double bonds 106, 113, 242 Cooling methods 2 Coproporphyrin 408 Cost of materials 94-95 Coumarin 238 INDEX 429 Coupling of diazonium compounds 305-308 Crocetin 233 Croconic acid 225 Crotonaldehyde 219 Crotonic acid 233 Cryptopyrrole 407 Cryptopyrrole carboxylic acid 408 Crystallisation 4-12 Crystal violet 328 Cupferron 177 Cuprous cyanide 291 Curtius reaction 153 Cyanidin 268 Cyanogen bromide and cyclic bases 364 Cyanohydrin synthesis 230 Cyclobutane dicarboxylic acid, ester of, 266 Cycloheptatriene carboxylic acid, ester of, 281 Cyclohexane 107, 381, 382 Cyclohexanol 379 Cyclo-octatetraene 114 Cyclopentadiene 113 Cyclopentanone carboxylic acid, ester of, 259 Cyclopropane derivatives 280 Cysteine 202 Cystine 202 Decalin 381 Dehydracetic acid 252, 267 Dehydrocholic acid 413 Dehydrogenation with selenium 416 Dehydroindigo 367 Delphinidin 268 Desmotropism 262 Desoxycholic acid 413 Deuteroporphyrin 409 Diacetyl 224 Diacetylsuccinic acid ester 267 Diacyl oxides 128 Dialkyl oxides 128 Dianisidine 187 y-Dianisylnitrogen 358 Diazoaminobenzene 282, 303 Diazobenzeneamide 289 Diazobenzeneimide 289 Diazo-components 305 Diazo-compounds, aliphatic, 271 aromatic, 281 Diazohydroxide 288 Diazomethane 271 determination of, 273 Diazonium hydroxide type 288 Diazonium salt solution 281 Diazophenol ether 307
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L A B O R A T O R Y M E T H O D S O
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PEEFACE TO THE TWENTY-FOUKTH EDITIO
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PEEFACE TO THE EEVISED (NINETEENTH)
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CONTENTS A. SOME GENERAL LABORATORY
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CONTENTS x III. NlTBO-COMPOUNDS AND
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CONTENTS xiii B. Aromatic Diazo-Com
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CONTENTS xv PAGE 5. Lactose and cas
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A. SOME GENERAL LABORATORY RULES Re
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PUKIFICATION OF OEGANIC SUBSTANCES
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CHOICE OF SOLVENT 5 The choice of t
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DISSOLVING THE SUBSTANCE then be di
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ISOLATION OF CEYSTALS 9 The steam-h
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FILTKATION 11 In order to remove th
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VACUUM DESICCATOKS 13 The consisten
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DISTILLATION 15 filter tube filled
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BATHS AND CONDENSEKS 17 may be allo
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FKACTIONAL DISTILLATION 19 The near
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VACUUM DISTILLATION 21 during vacuu
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HEATING 23 The two pieces of appara
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EFFECT OF PEESSUEE ON BOILING POINT
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DISTILLATION WITH STEAM 27 retorts,
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THEOKY OF STEAM DISTILLATION 29 On
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EVAPOKATION IN A VACUUM 31 to the p
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DEYING OF SOLUTIONS 33 determined b
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EXTKACTION APPAEATUS 35 The extract
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HEATING UNDEK PEESSUEE 37 in hydrog
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STIEEING AND SHAKING 39 reaction lo
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SINTEKING 41 the middle of the merc
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B. ORGANIC ANALYTICAL METHODS DETEC
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BBILSTBIN'S TEST 45 case remove gla
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DETEKMINATION OF NITKOGEN 47 rapid-
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FILLING THE COMBUSTION TUBE 49 Fill
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THE DUMAS METHOD 51 FIG. 34 CARRYIN
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THE DUMAS METHOD 53 bulb lowered fo
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DETEKMINATION OF CAKBON AND HYDEOGB
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THE DEYING APPAEATUS 57 cotton wool
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FILLING THE COMBUSTION TUBE 59 amou
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THE ABSOKPTION APPAEATUS 61 grease
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CAEEYING OUT THE COMBUSTION 63 Duri
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THE COMBUSTION 65 ously been specia
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THE COMBUSTION 67 the tube immediat
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DETERMINATION OF HALOGEN, SULPHUR,
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HALOGEN BY THE CAEIUS METHOD 71 out
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DETEKMINATION OF CHLOKINE AND BROMI
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DETEKMINATION OF CHLOKINE AND BROMI
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DETEKMINATION OF SULPHUE 77 tube. B
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DETEKMINATION OP HALOGEN 79 solutio
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DETEKMINATION OF THE METHOXY GEOUP
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DETEKMINATION OF THE ACETYL GKOUP 8
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DETEKMINATION OF ACTIVE HYDKOGEN 85
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DETEKMINATION OF MOLECULAK WEIGHT 8
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PKEVENTION OF ACCIDENTS 89 stances
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EQUIPMENT EEQUIEED BY THE BEGINNEE
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CHAPTBE I THE REPLACEMENT OF HYDROX
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ETHYL IODIDE FKOM ETHYL ALCOHOL 95
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EBPLACBMBNT OF HYDKOXYL BY HALOGEN
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EBPLACBMENT OF HYDKOXYL BY HALOGEN
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BENZYL CHLOKIDE FKOM TOLUENE 101 Us
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BKOMOBENZENE 103 The intermediate p
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BKOMOBENZENE 105 Grignard reaction
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PKEPAKATION OF AN OLEFINE 107 HC1 H
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PKEPAKATION OF AN OLEFINE 109 the c
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EBACTIONS OF OLEFINES 111 Thus ethy
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DIBNB SYNTHESIS' OF DIBLS 113 and,
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GLYCOL FKOM BTHYLBNB DIBKOMIDE 115
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ISOAMYL BTHBE 117 formaldehyde are
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HALOGEN CAEEIBES 119 The introducti
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CHAPTBE II CARBOXYLIC ACIDS AND THE
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ACID CHLOKIDES 123 The course of th
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BENZOYL PEKOXIDE 125 Experiments.
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ACID ANHYDKIDES 127 an excess of ac
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ACBTAMIDB 129 The - intermediate pr
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ACETAMIDE 131 Owing to the acyi gro
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POTASSIUM CYANATB AND UEBA 133 cool
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UEBA AND UEIC ACID FKOM UEINB 135 s
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ACETONITKILE 137 5. NITRILES (a) AC
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KEACTIONS OF NITEILBS 139 CH3.CN +
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BSTBES 141 pouring into 50 c.c. of
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BSTBES 143 the temperature, whilst
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INFLUENCE OF THE CATALYST 145 form
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ETHYL NITEITB 147 solution and then
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SAPONIFICATION 149 increases contin
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IODINE AND SAPONIFICATION VALUES 15
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THE CUETIUS KEACTION 153 (b) THE CU
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THE HOFMANN AND CURTIUS EBACTIONS 1
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NITEOMETHANB 157 to those used to e
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SILVBE FULMINATE 159 concentrated s
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NITKOBENZENE 161 if the reaction pr
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METHODS OF NITEATION 163 Nitro-grou
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ANILINE 165 3. REDUCTION OF A NITRO
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KEACTIONS OF ANILINE 167 three drop
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DIPHEJSTYLTHIOUKEA 169 a result of
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MBTA-NITEANILINB 171 with an equal
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BASICITY OF THE NITEANILINBS 173 On
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A K Y L H Y D K O X Y L A M I N E S
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NITKOSOHYDKOXYLAMINES 177 CH3 CH3 H
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NITKOSOBENZENE 179 5. NITROSOBENZEN
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CONDENSATION OF NITEOSO-COMPOUNDS 1
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HYDKAZOBENZENE 183 I H5C6.N-N.C6H5,
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AZOBENZENE 185 (75 c.c. of 22V-sodi
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THE BBNZIDINB KBAKKANGBMBNT HH HH H
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AZOXYBBNZBNB TO HYDKAZOBENZENE 189
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CHAPTBK IV 8ULPH0NIC ACIDS 1. BENZE
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TOLUENE-^-SULPHONIC ACID 193 toluen
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SULPHANILIC ACID 195 paste when rub
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SULPHONATION 197 and the aliphatic
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SULPHONATION 199 That this is the c
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SULPHINIC ACIDS 201 V SO2.NH2 / \ S
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CHAPTBK V ALDEHYDES 1. FORMALDEHYDE
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DBTEKMINATION OF FOKMALDEHYDE 205 e
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ACBTALDBHYDB 207 just-boiling mixtu
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ACBTALDBHYDB FKOM ACETYLENE 209 (6)
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ALDEHYDES 211 The aromatic aldehyde
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AUTOXIDATION 213 Thus the autoxidat
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KBACTION WITH AMMONIA 215 of an ald
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PAKALDBHYDB 217 more rapidly on hea
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CONDENSATION 219 a-acrose (dl-iiuct
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CANNIZZAKO'S KBACTION 221 tracted b
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THE ACYLOIN CONDENSATION 223 duct.
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THE PINACOLINE KEAKKANGEMENT 225 Th
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MANDELIC ACID 227 diphenylketene by
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ALANINB 229 rfZ-mandelic acid. Howe
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MOLBCULAK ASYMMBTKY 231 The amygdal
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CAKOTBNOIDS 233 used, with lead oxi
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SALICYLALDBHYDB 235 ing. While stil
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MECHANISM OF THE SYNTHESIS 237 This
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CHAPTBK VI PHENOLS AND ENOL8. KETO-
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PHENOLS AND BNOLS 241 Simple ketone
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OH BKOMINATION OF PHENOL 243 HOBr T
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BTHBKS OF PHENOLS 245 acids (method
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NITKOPHBNOLS 247 concentrated on a
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SALICYLIC ACID 249 In trinitrochlor
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ETHEL ACETOACETATE 251 Salicylic ac
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ACBTYLACBTONB. BBNZOYLACBTONB 253 m
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DIBTHYL MALONATB 255 bath at 40°-5
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KBTO-BNOL TAUTOMBKISM 257 separates
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ANALOGIES TO ACETOACETATE SYNTHESIS
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BKOMINATION AND BNOL CONTENT 261 th
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ALIPHATIC NITKO-COMPOUNDS 263 In be
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ACBTOACBTATB AND MALONATB SYNTHESES
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DBHYDKACBTIC ACID 267 HgC.CO.CH.COO
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CHAPTBK VII THE DIAZO-COMPOUNDS GEN
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DIAZOMBTHANB 271 a base, the salt o
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EBACTIONS OF DIAZOMBTHANB 273 it is
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GLYCINE BSTBK HYDKOCHLOKIDB 275 The
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HIPPUKIC ACID 277 This procedure wa
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STEAM DISTILLATION IN A PAKTIAL VAC
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DIAZOTISATION OF ANILINE 281 Benzen
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IODOBBNZBNE FKOM ANILINE 283 For pr
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IODOXYBBNZBNB 285 into a test tube,
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SOLID PHENYLDIAZONIUM CHLOKIDE 287
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PHENYLDIAZONIUM PBKBKOMIDB 289 Phen
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^-TOLUNITKILE FKOM ^-TOLUIDINE 291
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THE SANDMBYEK KBACTION 293 By perma
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SALVAKSAN 295 hydroxide solution, a
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PHBNYLHYDKAZINB 297 out turbidity.
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SYNTHESIS OF INDOLES 299 mentioned
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ANALYSIS OF AZO-DYBS 301 The coupli
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COUPLING OF ANILINE 303 Congo red i
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COUPLING KBACTION OF DIAZO-COMPOUND
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ANALOGOUS ACTION OF NITKOUS ACID 30
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CHAPTEK VIII QUINONOID COMPOUNDS 1.
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ANILINOQUINONE 0 0 The great affini
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2H '°> O=/~\=O + NH3 + H2N QUINONB
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^-NITKOSOBASES AND THBIK SALTS 315
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DETECTION OF NITKOSO-GKOUPS 317 mon
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QUINONBDIIMINBS 319 base (or of a s
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BINDSCHBDLBK'S GKEBN 321 disappear
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VI MBTHYLBNE BLUB 323 Methylene blu
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MALACHITE GKBBN 325 Oxidation of th
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TKIPHBNYLMBTHANB DYES 327 obtained
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TKIPHBNYLMBTHANB DYES 329 C,H,.NHj
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PHTHALBINS 331 of fuchsonimine. Thu
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COOH Since fluorescein is coloured
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QUINIZAKIN 335 collecting the subst
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CHAPTBK IX THE GEIGNAED AND FEIEDEL
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ACETOPHBNONB FKOM BKOMOBBNZBNE 339
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THE GRIGNARD KBACTION 341 Formaldeh
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BBNZOPHBNONB 343 necked bottle in s
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THE BBCKMANN KEAKKANGBMBNT 345 abou
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TKIPHBNYLCHLOKOMBTHANB 347 of 80 g.
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THE FKIEDEL-CKAFTS KBACTION 349 Whe
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THE FKIEDEL-CKAFTS KBACTION 351 H \
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HEXAPHENYLETHANE 353 a folded paper
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TBTKAPHBNYLHYDKAZINB 355 sibly as a
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FIXATION OF DIPHENYLNITKOGEN 357 go
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QUADKIVALBNT NITROGEN 359 sponding
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CHAPTBK X HETEEOCYCLIC COMPOUNDS 1.
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KNOEVENAGEL'S SYNTHESIS E JH II /-
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a-AMINOPYKIDINB 365 rH2 I 2 I -+ I
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QUINALDINB 367 the liberated quinol
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ATOPHAN. PHENYLGLYCINE 369 a-phenyl
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INDIGO FKOM o-NITKOBBNZALDBHYDB 371
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VAT DYEING 373 by reduction in alka
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ISATIN 375 The beautiful preparatio
Page 391 and 392: CATALYTIC HYDKOGBNATION 377 the sle
Page 393 and 394: USB OF NICKEL 379 Preparation of Pl
Page 395 and 396: CYCLOHEXANE 381 potassium carbonate
Page 397 and 398: CLEMMBNSEN'S METHOD 383 the higher
Page 399 and 400: ADIPIC ALDEHYDE FROM CYCLOHEXENE 38
Page 401 and 402: FURFURAL 387 product is complete. R
Page 403 and 404: HYDKOLYSIS OF CANE SUGAK 389 50 c.c
Page 405 and 406: LACTOSE AND CASEIN FKOM MILK 391 of
Page 407 and 408: d-GALACTOSE FKOM LACTOSE 393 Millon
Page 409 and 410: SOME KBMAKKS ON CAKBOHYDKATBS 395 n
Page 411 and 412: SOME KBMAKKS ON CAKBOHYDKATBS A hex
Page 413 and 414: I 0 III SOME KBMAKKS ON CAKBOHYDKAT
Page 415 and 416: SACCHAKIFICATION OF STAKCH 401 8. S
Page 417 and 418: MECHANISM OF FBKMBNTATION 403 ferme
Page 419 and 420: CAFFEINE FKOM TEA 405 cools the arg
Page 421 and 422: HABMIN FKOM OX BLOOD 407 12. HAEMIN
Page 423 and 424: PKOTOPOKPHYKIN 409 chemistry of the
Page 425 and 426: GLYCOCHOLIC ACID 411 plate to fit a
Page 427 and 428: DBSOXYCHOLIC ACID 413 the solid) is
Page 429 and 430: CHOLBSTBKOL 415 From a little alcoh
Page 431: BAKIUM DBSOXYCHOLATB 417 of desoxyc
Page 434 and 435: 420 LITBKATUKB OF ORGANIC CHEMISTKY
Page 436 and 437: 422 LITBKATUEB OF OKGANIC CHBMISTKY
Page 438 and 439: TABLE FOR CALCULATIONS IN THE DETER
Page 441: SUBJECT INDEX (The page numbers whi
Page 445 and 446: Fluorene 260 Fluorescein 326 Formal
Page 447 and 448: Nerolin 244 New fuchsine 329 Nickel
Page 449: Sublimation 26, 27 Substitution, ru
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