- Page 1 and 2: ORGANIC CHEMISTRY LABORATORY TECHNI
- Page 3 and 4: TABLE OF CONTENTS, IN BRIEF Preface
- Page 5 and 6: TABLE OF CONTENTS, IN DETAIL Chapte
- Page 7 and 8: Chapter 3: Crystallization 155 3.1
- Page 9 and 10: Chapter 5: Distillation 247 5.1 Ove
- Page 11 and 12: ABOUT THE AUTHOR LISA NICHOLS This
- Page 13 and 14: NOTE TO STUDENTS This resource is a
- Page 15 and 16: CHAPTER 1 GENERAL TECHNIQUES A Grig
- Page 17 and 18: 1.1 GLASSWARE AND EQUIPMENT 1.1.A P
- Page 19 and 20: Burners and tubing: Item Name: 1. T
- Page 21 and 22: 1.1.C CLAMPING Organic chemistry gl
- Page 23 and 24: 1.1.D GREASING JOINTS Ground glass
- Page 25 and 26: inside a hot oven (> 100 ˚C) as ac
- Page 27 and 28: 1.2 TRANSFERRING METHODS 1.2.A SOLI
- Page 29 and 30: 1.2.B.3 USING PASTEUR PIPETTES Past
- Page 31 and 32: The volume markings on a graduated
- Page 33 and 34: Figure 1.25: a) Red liquid to the 0
- Page 35 and 36: 1.2.B.5 DISPENSING HIGHLY VOLATILE
- Page 37 and 38: 1.2.C.1 STEP-BY-STEP PROCEDURES The
- Page 39 and 40: Figure 1.33: a) Screwing the needle
- Page 41 and 42: 20.The needle should be full of the
- Page 43 and 44: 1.2.C.2 INERT ATMOSPHERIC METHODS S
- Page 45 and 46: As safety is an important factor in
- Page 47: 1.3.B.2 BOILING STICKS (WOOD SPLINT
- Page 51 and 52: 1.3.E HOTPLATES Hotplates are perha
- Page 53 and 54: 1.3.G HEATING MANTLES Heating mantl
- Page 55 and 56: Oil baths are much like water baths
- Page 57 and 58: 1.3.J COOLING BATHS On occasion a s
- Page 59 and 60: Figure 1.60: a) Reflux apparatus, w
- Page 61 and 62: Figure 1.64: a+b) Condensation seen
- Page 63 and 64: 1.4 FILTERING METHODS 1.4.A OVERVIE
- Page 65 and 66: 1.4.D SUCTION FILTRATION 1.4.D.1 SU
- Page 67 and 68: 1.4.D.3 WATER ASPIRATOR A vacuum so
- Page 69 and 70: Figure 1.75: a) Placing the Buchner
- Page 71 and 72: 9. Rinse the solid on the filter pa
- Page 73 and 74: 1.4.E HOT FILTRATION 1.4.E.1 HOT FI
- Page 75 and 76: 1.4.E.2 STEP-BY-STEP PROCEDURES Hot
- Page 77 and 78: 1.4.E.3 HOT FILTRATION SUMMARY Prep
- Page 79 and 80: 1.4.G CENTRIFUGATION Centrifugation
- Page 81 and 82: CHAPTER 2 CHROMATOGRAPHY A mixture
- Page 83 and 84: 2.1 CHROMATOGRAPHY GENERALITIES Chr
- Page 85 and 86: 2.1.B GENERAL SEPARATION THEORY The
- Page 87 and 88: 2.2.B USES OF TLC TLC is a common t
- Page 89 and 90: 2.2.B.2.B MONITORING A REACTION BY
- Page 91 and 92: 2.2.C THE RETENTION FACTOR (R F ) A
- Page 93 and 94: 2.2.D SEPARATION THEORY 2.2.D.1 GEN
- Page 95 and 96: 2.2.D.2 STRUCTURAL CONSIDERATIONS T
- Page 97 and 98: 2.2.D.3 MOBILE PHASE POLARITY The a
- Page 99 and 100:
Prepare the TLC Chamber and Plate 2
- Page 101 and 102:
Figure 2.26: a) Using forceps to pl
- Page 103 and 104:
2.2.E.3 TLC TROUBLESHOOTING 2.2.E.3
- Page 105 and 106:
2.2.E.5 NOTEBOOK RECORD OF TLC’S
- Page 107 and 108:
2.2.F.2 ULTRAVIOLET ABSORPTION The
- Page 109 and 110:
2.2.F.4 CHEMICAL STAINS There are a
- Page 111 and 112:
2) REACTION PATHWAYS The p-anisalde
- Page 113 and 114:
2.2.F.4.D PHOSPHOMOLYBDIC ACID STAI
- Page 115 and 116:
2.2.F.5 VISUALIZATION TROUBLESHOOTI
- Page 117 and 118:
2.2.F.5.C A STAIN’S COLOR FADED O
- Page 119 and 120:
2.3 COLUMN CHROMATOGRAPHY Column ch
- Page 121 and 122:
2.3.A.2 STEP-BY-STEP PROCEDURES Fig
- Page 123 and 124:
Figure 2.55: a) Jostling the column
- Page 125 and 126:
16.Gently rinse the sides of the co
- Page 127 and 128:
Figure 2.60: a) Elution, b) Additio
- Page 129 and 130:
Figure 2.63: a) Eluted TLC plates o
- Page 131 and 132:
2.3.A.3 MACROSCALE COLUMN SUMMARY M
- Page 133 and 134:
2.3.A.4 C THE BANDS ARE ELUTING UNE
- Page 135 and 136:
4. Gently clamp the pipette column
- Page 137 and 138:
Elute the Column and Collect Fracti
- Page 139 and 140:
2.4 GAS CHROMATOGRAPHY (GC) 2.4.A O
- Page 141 and 142:
2.4.B.2 IDENTIFYING COMPONENTS Due
- Page 143 and 144:
IMF’s with the column coating spe
- Page 145 and 146:
2.4.D QUANTITATING WITH GC 2.4.D.1
- Page 147 and 148:
2.4.D.2 USING A CALIBRATION CURVE O
- Page 149 and 150:
2.4.E GC PARAMETERS There are many
- Page 151 and 152:
2.4.E.3 OVEN TEMPERATURE The temper
- Page 153 and 154:
2.4.F SAMPLE PREPARATION Liquid GC
- Page 155 and 156:
CHAPTER 3 CRYSTALLIZATION Time-laps
- Page 157 and 158:
3.1 OVERVIEW OF CRYSTALLIZATION In
- Page 159 and 160:
To demonstrate, a mixture containin
- Page 161 and 162:
3.3.B GENERAL PROCEDURES FOR REMOVI
- Page 163 and 164:
3.3.D USING SOLUBILITY DATA If you
- Page 165 and 166:
3.3.F MIXED SOLVENTS When no single
- Page 167 and 168:
3.4 CRYSTALLIZATION THEORY 3.4.A PU
- Page 169 and 170:
3.4.C USING THE MINIMUM AMOUNT OF H
- Page 171 and 172:
To demonstrate the importance of us
- Page 173 and 174:
3.4.E QUANTITATING CRYSTALLIZATION
- Page 175 and 176:
3.4.E.2 WITH AN IMPURITY OF SIMILAR
- Page 177 and 178:
A “second crop” solid should al
- Page 179 and 180:
3.5 PROCEDURAL GENERALITIES 3.5.A G
- Page 181 and 182:
3.5.C CHARCOAL Activated charcoal i
- Page 183 and 184:
3.5.D COOLING SLOWLY After a soluti
- Page 185 and 186:
There are a few others methods that
- Page 187 and 188:
Figure 3.50: a) Impure NBS added to
- Page 189 and 190:
Figure 3.53: a-c) Cooling and cryst
- Page 191 and 192:
3.6.C USING SOLVENTS OTHER THAN WAT
- Page 193 and 194:
3.6.D MIXED SOLVENT CRYSTALLIZATION
- Page 195 and 196:
3.6.E MIXED SOLVENT SUMMARY Find a
- Page 197 and 198:
3.6.F.2 CRYSTALLIZATION DOESN’T H
- Page 199 and 200:
3.6.F.4 LIQUID DROPLETS FORM (THE S
- Page 201 and 202:
CHAPTER 4 EXTRACTION Organic solven
- Page 203 and 204:
4.1 OVERVIEW OF EXTRACTION “Extra
- Page 205 and 206:
4.2.C SELECTIVE REMOVAL OF COMPONEN
- Page 207 and 208:
4.3.B HOW TO DETERMINE THE AQUEOUS
- Page 209 and 210:
4.4.B CHOOSING A SOLVENT WITH SOLUB
- Page 211 and 212:
4.4.D MULTIPLE EXTRACTIONS 4.4.D.1
- Page 213 and 214:
4.4.D.2 QUANTITATING MULTIPLE EXTRA
- Page 215 and 216:
4.5 STEP-BY-STEP PROCEDURES 4.5.A S
- Page 217 and 218:
Figure 4.24: a) Closed and open sto
- Page 219 and 220:
Figure 4.27: a) Taking the stopper
- Page 221 and 222:
4.5.B SINGLE EXTRACTION SUMMARY Use
- Page 223 and 224:
If the organic layer (incorrect) wa
- Page 225 and 226:
4.5.D TROUBLESHOOTING This section
- Page 227 and 228:
Figure 4.34: a) An emulsion with bi
- Page 229 and 230:
3. Gently mix the two solutions usi
- Page 231 and 232:
O + cat. H 2 SO 4 O OH HO O acetic
- Page 233 and 234:
Testing the pH After a Wash To test
- Page 235 and 236:
If drying agents are used to remove
- Page 237 and 238:
4.6.C DRYING AGENTS 4.6.C.1 WHY THE
- Page 239 and 240:
In some procedures Na 2 SO 4 or CaC
- Page 241 and 242:
Figure 4.53: a) Wet hydrate of Na 2
- Page 243 and 244:
4.7.B SODIUM BICARBONATE WASHES An
- Page 245 and 246:
4.7.C.3 EXTRACTING ACID, BASE, AND
- Page 247 and 248:
CHAPTER 5 DISTILLATION Steam distil
- Page 249 and 250:
5.1 OVERVIEW OF DISTILLATION Distil
- Page 251 and 252:
5.2 SIMPLE DISTILLATION 5.2.A USES
- Page 253 and 254:
Figure 5.7: a) Benzaldehyde reagent
- Page 255 and 256:
5.2.B.2 PURIFICATION POTENTIAL A si
- Page 257 and 258:
In this distillation, the differenc
- Page 259 and 260:
Every mixture has its own distillat
- Page 261 and 262:
Figure 5.15: a) Distillation curve
- Page 263 and 264:
Azeotropic mixtures come in two for
- Page 265 and 266:
5.2.C.2 SIMPLE DISTILLATION PROCEDU
- Page 267 and 268:
5. Attach a three-way adapter (or
- Page 269 and 270:
15.A completed distillation apparat
- Page 271 and 272:
The thermometer bulb must be fully
- Page 273 and 274:
5.2.C.4 VARIATIONS A few variations
- Page 275 and 276:
If glass wool is unavailable, alumi
- Page 277 and 278:
5.2.D.3 SHORT-PATH DISTILLATION An
- Page 279 and 280:
The concepts of a fractional distil
- Page 281 and 282:
5.3.C USES OF FRACTIONAL DISTILLATI
- Page 283 and 284:
Figure 5.44: a) Removal of glass wo
- Page 285 and 286:
5.4 VACUUM DISTILLATION 5.4.A OVERV
- Page 287 and 288:
5.4.C STEP-BY-STEP PROCEDURES 5.4.C
- Page 289 and 290:
Figure 5.52: a) Stir plate with woo
- Page 291 and 292:
5.4.C.2 VACUUM DISTILLATION SUMMARY
- Page 293 and 294:
5.5.C SEPARATION THEORY Although st
- Page 295 and 296:
Figure 5.59: Steam distillation var
- Page 297 and 298:
Figure 5.62: a+b) Distillate with o
- Page 299 and 300:
5.5.D.2 STEAM DISTILLATION SUMMARY
- Page 301 and 302:
5.6.B STEP-BY-STEP PROCEDURES 5.6.B
- Page 303 and 304:
. If the expected compound is a liq
- Page 305 and 306:
5.6.C TROUBLESHOOTING 1. If the sol
- Page 307 and 308:
CHAPTER 6 MISCELLANEOUS TECHNIQUES
- Page 309 and 310:
6.1 MELTING POINT 6.1.A OVERVIEW OF
- Page 311 and 312:
6.1.B.2 ASSESSING PURITY A second r
- Page 313 and 314:
6.1.C MELTING POINT THEORY 6.1.C.1
- Page 315 and 316:
6.1.C.2.B BROADENING OF THE MELTING
- Page 317 and 318:
6.1.D.2 MELTING POINT APPARATUS Fig
- Page 319 and 320:
. The sample may sublime instead of
- Page 321 and 322:
7. If the expected melting point of
- Page 323 and 324:
6.1.E MIXED MELTING POINTS As previ
- Page 325 and 326:
6.2.B.2 REFLUX METHOD A reflux setu
- Page 327 and 328:
6.2.B.3.B THIELE TUBE PROCEDURE Fig
- Page 329 and 330:
6.2.B.3.C THIELE TUBE SUMMARY Fill
- Page 331 and 332:
6.3.A OVERVIEW OF SUBLIMATION Some
- Page 333 and 334:
Figure 6.31: Time-lapse sublimation
- Page 335 and 336:
Figure 6.34: a) Small scale sublima
- Page 337 and 338:
6.3.B.3 VACUUM SUBLIMATION SUMMARY
- Page 339 and 340:
6.4.B FLOWCHARTS In some teaching l
- Page 341 and 342:
3. Unsaturated Hydrocarbons (Alkene
- Page 343 and 344:
Permanganate (Baeyer) Test pH Test
- Page 345 and 346:
6.4.D.2 BENEDICT’S TEST The Bened
- Page 347 and 348:
6.4.D.3 BICARBONATE TEST Carboxylic
- Page 349 and 350:
6.4.D.5 CHROMIC ACID (JONES) TEST A
- Page 351 and 352:
6.4.D.7 FERRIC HYDROXAMATE TEST The
- Page 353 and 354:
6.4.D.9 LUCAS TEST The Lucas Reagen
- Page 355 and 356:
6.4.D.11 pH TEST Carboxylic acids a
- Page 357 and 358:
6.4.D.13 SILVER NITRATE TEST A dilu
- Page 359 and 360:
6.4.D.15 TOLLENS TEST The Tollens r
- Page 361 and 362:
CHAPTER 7 SUMMARIES 7.1 Flame-Dryin
- Page 363 and 364:
7.2 USING CALIBRATED GLASS PIPETTES
- Page 365 and 366:
7.4 REFLUX Pour liquid into the fla
- Page 367 and 368:
7.6 HOT FILTRATION Prepare a fluted
- Page 369 and 370:
7.8 TLC VISUALIZATION METHODS Ultra
- Page 371 and 372:
7.10 PIPETTE COLUMN CHROMATOGRAPHY
- Page 373 and 374:
7.12 TESTING MIXED SOLVENTS FOR CRY
- Page 375 and 376:
7.14 MIXED SOLVENT CRYSTALLIZATION
- Page 377 and 378:
7.16 MULTIPLE EXTRACTIONS Organic l
- Page 379 and 380:
7.18 TESTING THE pH AFTER A WASH If
- Page 381 and 382:
7.20 ACID-BASE EXTRACTION a) Extrac
- Page 383 and 384:
7.22 FRACTIONAL DISTILLATION Figure
- Page 385 and 386:
7.24 STEAM DISTILLATION Figure 7.12
- Page 387 and 388:
7.26 MELTING POINTS Load the sample
- Page 389:
7.28 VACUUM SUBLIMATION Figure 7.14