Laboratory Methods of Organic Chemistry - Sciencemadness Dot Org

More documents

Recommendations

Info

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 progress 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. linolenic 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 rewritten 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
Page 1: L A B O R A T O R Y M E T H O D S O
Page 5 and 6: PEEFACE TO THE EEVISED (NINETEENTH)
Page 7 and 8: CONTENTS A. SOME GENERAL LABORATORY
Page 9 and 10: CONTENTS x III. NlTBO-COMPOUNDS AND
Page 11 and 12: CONTENTS xiii B. Aromatic Diazo-Com
Page 13 and 14: CONTENTS xv PAGE 5. Lactose and cas
Page 15 and 16: A. SOME GENERAL LABORATORY RULES Re
Page 17 and 18: PUKIFICATION OF OEGANIC SUBSTANCES
Page 19 and 20: CHOICE OF SOLVENT 5 The choice of t
Page 21 and 22: DISSOLVING THE SUBSTANCE then be di
Page 23 and 24: ISOLATION OF CEYSTALS 9 The steam-h
Page 25 and 26: FILTKATION 11 In order to remove th
Page 27 and 28: VACUUM DESICCATOKS 13 The consisten
Page 29 and 30: DISTILLATION 15 filter tube filled
Page 31 and 32: BATHS AND CONDENSEKS 17 may be allo
Page 33 and 34: FKACTIONAL DISTILLATION 19 The near
Page 35 and 36: VACUUM DISTILLATION 21 during vacuu
Page 37 and 38: HEATING 23 The two pieces of appara
Page 39 and 40: EFFECT OF PEESSUEE ON BOILING POINT
Page 41 and 42: DISTILLATION WITH STEAM 27 retorts,
Page 43 and 44: THEOKY OF STEAM DISTILLATION 29 On
Page 45 and 46: EVAPOKATION IN A VACUUM 31 to the p
Page 47 and 48: DEYING OF SOLUTIONS 33 determined b
Page 49 and 50: EXTKACTION APPAEATUS 35 The extract
Page 51 and 52: HEATING UNDEK PEESSUEE 37 in hydrog
Page 53 and 54:
STIEEING AND SHAKING 39 reaction lo
Page 55 and 56:
SINTEKING 41 the middle of the merc
Page 57 and 58:
B. ORGANIC ANALYTICAL METHODS DETEC
Page 59 and 60:
BBILSTBIN'S TEST 45 case remove gla
Page 61 and 62:
DETEKMINATION OF NITKOGEN 47 rapid-
Page 63 and 64:
FILLING THE COMBUSTION TUBE 49 Fill
Page 65 and 66:
THE DUMAS METHOD 51 FIG. 34 CARRYIN
Page 67 and 68:
THE DUMAS METHOD 53 bulb lowered fo
Page 69 and 70:
DETEKMINATION OF CAKBON AND HYDEOGB
Page 71 and 72:
THE DEYING APPAEATUS 57 cotton wool
Page 73 and 74:
FILLING THE COMBUSTION TUBE 59 amou
Page 75 and 76:
THE ABSOKPTION APPAEATUS 61 grease
Page 77 and 78:
CAEEYING OUT THE COMBUSTION 63 Duri
Page 79 and 80:
THE COMBUSTION 65 ously been specia
Page 81 and 82:
THE COMBUSTION 67 the tube immediat
Page 83 and 84:
DETERMINATION OF HALOGEN, SULPHUR,
Page 85 and 86:
HALOGEN BY THE CAEIUS METHOD 71 out
Page 87 and 88:
DETEKMINATION OF CHLOKINE AND BROMI
Page 89 and 90:
DETEKMINATION OF CHLOKINE AND BROMI
Page 91 and 92:
DETEKMINATION OF SULPHUE 77 tube. B
Page 93 and 94:
DETEKMINATION OP HALOGEN 79 solutio
Page 95 and 96:
DETEKMINATION OF THE METHOXY GEOUP
Page 97 and 98:
DETEKMINATION OF THE ACETYL GKOUP 8
Page 99 and 100:
DETEKMINATION OF ACTIVE HYDKOGEN 85
Page 101 and 102:
DETEKMINATION OF MOLECULAK WEIGHT 8
Page 103 and 104:
PKEVENTION OF ACCIDENTS 89 stances
Page 105 and 106:
EQUIPMENT EEQUIEED BY THE BEGINNEE
Page 107 and 108:
CHAPTBE I THE REPLACEMENT OF HYDROX
Page 109 and 110:
ETHYL IODIDE FKOM ETHYL ALCOHOL 95
Page 111 and 112:
EBPLACBMBNT OF HYDKOXYL BY HALOGEN
Page 113 and 114:
EBPLACBMENT OF HYDKOXYL BY HALOGEN
Page 115 and 116:
BENZYL CHLOKIDE FKOM TOLUENE 101 Us
Page 117 and 118:
BKOMOBENZENE 103 The intermediate p
Page 119 and 120:
BKOMOBENZENE 105 Grignard reaction
Page 121 and 122:
PKEPAKATION OF AN OLEFINE 107 HC1 H
Page 123 and 124:
PKEPAKATION OF AN OLEFINE 109 the c
Page 125 and 126:
EBACTIONS OF OLEFINES 111 Thus ethy
Page 127 and 128:
DIBNB SYNTHESIS' OF DIBLS 113 and,
Page 129 and 130:
GLYCOL FKOM BTHYLBNB DIBKOMIDE 115
Page 131 and 132:
ISOAMYL BTHBE 117 formaldehyde are
Page 133 and 134:
HALOGEN CAEEIBES 119 The introducti
Page 135 and 136:
CHAPTBE II CARBOXYLIC ACIDS AND THE
Page 137 and 138:
ACID CHLOKIDES 123 The course of th
Page 139 and 140:
BENZOYL PEKOXIDE 125 Experiments.
Page 141 and 142:
ACID ANHYDKIDES 127 an excess of ac
Page 143 and 144:
ACBTAMIDB 129 The - intermediate pr
Page 145 and 146:
ACETAMIDE 131 Owing to the acyi gro
Page 147 and 148:
POTASSIUM CYANATB AND UEBA 133 cool
Page 149 and 150:
UEBA AND UEIC ACID FKOM UEINB 135 s
Page 151 and 152:
ACETONITKILE 137 5. NITRILES (a) AC
Page 153 and 154:
KEACTIONS OF NITEILBS 139 CH3.CN +
Page 155 and 156:
BSTBES 141 pouring into 50 c.c. of
Page 157 and 158:
BSTBES 143 the temperature, whilst
Page 159 and 160:
INFLUENCE OF THE CATALYST 145 form
Page 161 and 162:
ETHYL NITEITB 147 solution and then
Page 163 and 164:
SAPONIFICATION 149 increases contin
Page 165 and 166:
IODINE AND SAPONIFICATION VALUES 15
Page 167 and 168:
THE CUETIUS KEACTION 153 (b) THE CU
Page 169 and 170:
THE HOFMANN AND CURTIUS EBACTIONS 1
Page 171 and 172:
NITEOMETHANB 157 to those used to e
Page 173 and 174:
SILVBE FULMINATE 159 concentrated s
Page 175 and 176:
NITKOBENZENE 161 if the reaction pr
Page 177 and 178:
METHODS OF NITEATION 163 Nitro-grou
Page 179 and 180:
ANILINE 165 3. REDUCTION OF A NITRO
Page 181 and 182:
KEACTIONS OF ANILINE 167 three drop
Page 183 and 184:
DIPHEJSTYLTHIOUKEA 169 a result of
Page 185 and 186:
MBTA-NITEANILINB 171 with an equal
Page 187 and 188:
BASICITY OF THE NITEANILINBS 173 On
Page 189 and 190:
A K Y L H Y D K O X Y L A M I N E S
Page 191 and 192:
NITKOSOHYDKOXYLAMINES 177 CH3 CH3 H
Page 193 and 194:
NITKOSOBENZENE 179 5. NITROSOBENZEN
Page 195 and 196:
CONDENSATION OF NITEOSO-COMPOUNDS 1
Page 197 and 198:
HYDKAZOBENZENE 183 I H5C6.N-N.C6H5,
Page 199 and 200:
AZOBENZENE 185 (75 c.c. of 22V-sodi
Page 201 and 202:
THE BBNZIDINB KBAKKANGBMBNT HH HH H
Page 203 and 204:
AZOXYBBNZBNB TO HYDKAZOBENZENE 189
Page 205 and 206:
CHAPTBK IV 8ULPH0NIC ACIDS 1. BENZE
Page 207 and 208:
TOLUENE-^-SULPHONIC ACID 193 toluen
Page 209 and 210:
SULPHANILIC ACID 195 paste when rub
Page 211 and 212:
SULPHONATION 197 and the aliphatic
Page 213 and 214:
SULPHONATION 199 That this is the c
Page 215 and 216:
SULPHINIC ACIDS 201 V SO2.NH2 / \ S
Page 217 and 218:
CHAPTBK V ALDEHYDES 1. FORMALDEHYDE
Page 219 and 220:
DBTEKMINATION OF FOKMALDEHYDE 205 e
Page 221 and 222:
ACBTALDBHYDB 207 just-boiling mixtu
Page 223 and 224:
ACBTALDBHYDB FKOM ACETYLENE 209 (6)
Page 225 and 226:
ALDEHYDES 211 The aromatic aldehyde
Page 227 and 228:
AUTOXIDATION 213 Thus the autoxidat
Page 229 and 230:
KBACTION WITH AMMONIA 215 of an ald
Page 231 and 232:
PAKALDBHYDB 217 more rapidly on hea
Page 233 and 234:
CONDENSATION 219 a-acrose (dl-iiuct
Page 235 and 236:
CANNIZZAKO'S KBACTION 221 tracted b
Page 237 and 238:
THE ACYLOIN CONDENSATION 223 duct.
Page 239 and 240:
THE PINACOLINE KEAKKANGEMENT 225 Th
Page 241 and 242:
MANDELIC ACID 227 diphenylketene by
Page 243 and 244:
ALANINB 229 rfZ-mandelic acid. Howe
Page 245 and 246:
MOLBCULAK ASYMMBTKY 231 The amygdal
Page 247 and 248:
CAKOTBNOIDS 233 used, with lead oxi
Page 249 and 250:
SALICYLALDBHYDB 235 ing. While stil
Page 251 and 252:
MECHANISM OF THE SYNTHESIS 237 This
Page 253 and 254:
CHAPTBK VI PHENOLS AND ENOL8. KETO-
Page 255 and 256:
PHENOLS AND BNOLS 241 Simple ketone
Page 257 and 258:
OH BKOMINATION OF PHENOL 243 HOBr T
Page 259 and 260:
BTHBKS OF PHENOLS 245 acids (method
Page 261 and 262:
NITKOPHBNOLS 247 concentrated on a
Page 263 and 264:
SALICYLIC ACID 249 In trinitrochlor
Page 265 and 266:
ETHEL ACETOACETATE 251 Salicylic ac
Page 267 and 268:
ACBTYLACBTONB. BBNZOYLACBTONB 253 m
Page 269 and 270:
DIBTHYL MALONATB 255 bath at 40°-5
Page 271 and 272:
KBTO-BNOL TAUTOMBKISM 257 separates
Page 273 and 274:
ANALOGIES TO ACETOACETATE SYNTHESIS
Page 275 and 276:
BKOMINATION AND BNOL CONTENT 261 th
Page 277 and 278:
ALIPHATIC NITKO-COMPOUNDS 263 In be
Page 279 and 280:
ACBTOACBTATB AND MALONATB SYNTHESES
Page 281 and 282:
DBHYDKACBTIC ACID 267 HgC.CO.CH.COO
Page 283 and 284:
CHAPTBK VII THE DIAZO-COMPOUNDS GEN
Page 285 and 286:
DIAZOMBTHANB 271 a base, the salt o
Page 287 and 288:
EBACTIONS OF DIAZOMBTHANB 273 it is
Page 289 and 290:
GLYCINE BSTBK HYDKOCHLOKIDB 275 The
Page 291 and 292:
HIPPUKIC ACID 277 This procedure wa
Page 293 and 294:
STEAM DISTILLATION IN A PAKTIAL VAC
Page 295 and 296:
DIAZOTISATION OF ANILINE 281 Benzen
Page 297 and 298:
IODOBBNZBNE FKOM ANILINE 283 For pr
Page 299 and 300:
IODOXYBBNZBNB 285 into a test tube,
Page 301 and 302:
SOLID PHENYLDIAZONIUM CHLOKIDE 287
Page 303 and 304:
PHENYLDIAZONIUM PBKBKOMIDB 289 Phen
Page 305 and 306:
^-TOLUNITKILE FKOM ^-TOLUIDINE 291
Page 307 and 308:
THE SANDMBYEK KBACTION 293 By perma
Page 309 and 310:
SALVAKSAN 295 hydroxide solution, a
Page 311 and 312:
PHBNYLHYDKAZINB 297 out turbidity.
Page 313 and 314:
SYNTHESIS OF INDOLES 299 mentioned
Page 315 and 316:
ANALYSIS OF AZO-DYBS 301 The coupli
Page 317 and 318:
COUPLING OF ANILINE 303 Congo red i
Page 319 and 320:
COUPLING KBACTION OF DIAZO-COMPOUND
Page 321 and 322:
ANALOGOUS ACTION OF NITKOUS ACID 30
Page 323 and 324:
CHAPTEK VIII QUINONOID COMPOUNDS 1.
Page 325 and 326:
ANILINOQUINONE 0 0 The great affini
Page 327 and 328:
2H '°> O=/~\=O + NH3 + H2N QUINONB
Page 329 and 330:
^-NITKOSOBASES AND THBIK SALTS 315
Page 331 and 332:
DETECTION OF NITKOSO-GKOUPS 317 mon
Page 333 and 334:
QUINONBDIIMINBS 319 base (or of a s
Page 335 and 336:
BINDSCHBDLBK'S GKEBN 321 disappear
Page 337 and 338:
VI MBTHYLBNE BLUB 323 Methylene blu
Page 339 and 340:
MALACHITE GKBBN 325 Oxidation of th
Page 341 and 342:
TKIPHBNYLMBTHANB DYES 327 obtained
Page 343 and 344:
TKIPHBNYLMBTHANB DYES 329 C,H,.NHj
Page 345 and 346:
PHTHALBINS 331 of fuchsonimine. Thu
Page 347 and 348:
COOH Since fluorescein is coloured
Page 349 and 350:
QUINIZAKIN 335 collecting the subst
Page 351 and 352:
CHAPTBK IX THE GEIGNAED AND FEIEDEL
Page 353 and 354:
ACETOPHBNONB FKOM BKOMOBBNZBNE 339
Page 355 and 356:
THE GRIGNARD KBACTION 341 Formaldeh
Page 357 and 358:
BBNZOPHBNONB 343 necked bottle in s
Page 359 and 360:
THE BBCKMANN KEAKKANGBMBNT 345 abou
Page 361 and 362:
TKIPHBNYLCHLOKOMBTHANB 347 of 80 g.
Page 363 and 364:
THE FKIEDEL-CKAFTS KBACTION 349 Whe
Page 365 and 366:
THE FKIEDEL-CKAFTS KBACTION 351 H \
Page 367 and 368:
HEXAPHENYLETHANE 353 a folded paper
Page 369 and 370:
TBTKAPHBNYLHYDKAZINB 355 sibly as a
Page 371 and 372:
FIXATION OF DIPHENYLNITKOGEN 357 go
Page 373 and 374:
QUADKIVALBNT NITROGEN 359 sponding
Page 375 and 376:
CHAPTBK X HETEEOCYCLIC COMPOUNDS 1.
Page 377 and 378:
KNOEVENAGEL'S SYNTHESIS E JH II /-
Page 379 and 380:
a-AMINOPYKIDINB 365 rH2 I 2 I -+ I
Page 381 and 382:
QUINALDINB 367 the liberated quinol
Page 383 and 384:
ATOPHAN. PHENYLGLYCINE 369 a-phenyl
Page 385 and 386:
INDIGO FKOM o-NITKOBBNZALDBHYDB 371
Page 387 and 388:
VAT DYEING 373 by reduction in alka
Page 389 and 390:
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 and 442:
SUBJECT INDEX (The page numbers whi
Page 443 and 444:
Cannizzaro's reaction 220 Carbimide
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
show all

Laboratory Methods of Organic Chemistry - Sciencemadness Dot Org

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?