Organic Chemistry Laboratory Techniques, 2016a

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Chapter 4: Extraction 201 4.1 Overview of Extraction 203 4.5 Step-by-Step Procedures 215 4.2 Uses of Extraction 204 4.5.A Single Extraction 215 4.2.A Extracting Natural Compounds 204 4.5.B Single Extraction Summary 221 4.2.B Transferring Compounds from Layers 204 4.5.C Multiple Extractions 222 4.2.C Selective Removal of Components 205 Organic Layer is on the Top 222 Organic Layer is on the Bottom 224 4.3 Which Layer is Which? 206 4.5.D Troubleshooting 225 4.3.A Density 206 There is Only One Layer 225 4.3.B How To Determine the Aqueous Layer 207 There are Three Layers 225 There in Insoluble Material at the 225 Interface 4.4 Extraction Theory 208 The Interface Cannot Be Seen 226 4.4.A Partition / Distribution Coefficient (K) 208 The Layers Don't Separate Well 226 (An Emulsion Formed) 4.4.B Choosing a Solvent with Solubility Data 209 4.5.E Microscale Extractions 228 4.4.C Quantitating Single Extraction 210 4.4.D Multiple Extractions 211 4.6 Reaction Work-ups 230 Overview of Multiple Extraction 211 4.6.A Purpose of a Work-up 230 Quantitating Multiple Extraction 213 4.6.B Common Washes 230 Water 230 Sodium Bicarbonate and Sodium 232 Carbonate Brine (Saturated NaCl) 234 4.6.C Drying Agents 237 Why They are Used 237 Types of Drying Agents 238 Drying Agents Procedure 240 4.7 Acid-Base Extraction 242 4.7.A How They Work 242 4.7.B Sodium Bicarbonate Washes 243 4.7.C Mixtures of Acids and Bases 244 Extracting Bases 244 Extracting Carboxylic Acids Vs. 244 Phenols Extracting Acid, Base, and Neutral Components 245 Organic Chemistry Laboratory Techniques | Nichols | Page 8
Chapter 5: Distillation 247 5.1 Overview of Distillation 249 5.4 Vacuum Distillation 285 5.2 Simple Distillation 251 5.4.A Overview of Vacuum Distillation 285 5.2.A Uses of Simple Distillation 251 5.4.B Predicting the Boiling Temperature 286 Concentration of Alcohol 251 5.3.C Step-by-Step Procedures 287 Distilled Water 252 Vacuum Distillation Procedure 287 Purification of Reagents + Products 252 Vacuum Distillation Summary 291 5.2.B Separation Theory 254 Raoult’s and Dalton’s Laws 254 5.5 Steam Distillation 292 Purification Potential 255 5.5.A Overview of Steam Distillation 292 Distillation Curves 258 5.5.B Uses of Steam Distillation 292 Distilling Temperatures 260 5.5.C Separation Theory 293 Azeotropes 262 5.5.D Step-by-Step Procedures 294 5.2.C Step-by-Step Procedures 264 Steam Distillation Procedure 294 Condenser Hoses 264 Steam Distillation Summary 299 Simple Distillation Procedure 265 Simple Distillation Summary 272 5.6 Rotary Evaporation 300 Variations 273 5.6.A Overview of Rotary Evaporation 300 Troubleshooting 274 5.6.B Step-by-Step Procedures 301 Insulation 274 Rotary Evaporation Procedure 301 5.2.D Microscale Distillation 276 Rotary Evaporation Summary 304 Semi-Microscale 276 5.6.C Troubleshooting 305 Hickman Head 276 Short-Path Distillation 277 5.3 Fractional Distillation 278 5.3.A Theory of Fractional Distillation 278 5.3.B Fractionating Columns 279 5.3.C Uses of Fractional Distillation 281 Oil Refining 281 Purification of Reagents + Products 281 5.3.D Step-by-Step Procedures 282 Fractional Distillation Procedure 282 Fractional Distillation Summary 284 Organic Chemistry Laboratory Techniques | Nichols | Page 9
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: Chapter 3: Crystallization 155 3.1
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 and 48: 1.3.B.2 BOILING STICKS (WOOD SPLINT
Page 49 and 50: 1.3.D BUNSEN BURNERS Bunsen burners
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
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1.4.D SUCTION FILTRATION 1.4.D.1 SU
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1.4.D.3 WATER ASPIRATOR A vacuum so
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Figure 1.75: a) Placing the Buchner
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9. Rinse the solid on the filter pa
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1.4.E HOT FILTRATION 1.4.E.1 HOT FI
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1.4.E.2 STEP-BY-STEP PROCEDURES Hot
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1.4.E.3 HOT FILTRATION SUMMARY Prep
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1.4.G CENTRIFUGATION Centrifugation
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CHAPTER 2 CHROMATOGRAPHY A mixture
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2.1 CHROMATOGRAPHY GENERALITIES Chr
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2.1.B GENERAL SEPARATION THEORY The
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2.2.B USES OF TLC TLC is a common t
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2.2.B.2.B MONITORING A REACTION BY
Page 91 and 92:
2.2.C THE RETENTION FACTOR (R F ) A
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2.2.D SEPARATION THEORY 2.2.D.1 GEN
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2.2.D.2 STRUCTURAL CONSIDERATIONS T
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2.2.D.3 MOBILE PHASE POLARITY The a
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Prepare the TLC Chamber and Plate 2
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Figure 2.26: a) Using forceps to pl
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2.2.E.3 TLC TROUBLESHOOTING 2.2.E.3
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2.2.E.5 NOTEBOOK RECORD OF TLC’S
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2.2.F.2 ULTRAVIOLET ABSORPTION The
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2.2.F.4 CHEMICAL STAINS There are a
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2) REACTION PATHWAYS The p-anisalde
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2.2.F.4.D PHOSPHOMOLYBDIC ACID STAI
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2.2.F.5 VISUALIZATION TROUBLESHOOTI
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2.2.F.5.C A STAIN’S COLOR FADED O
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2.3 COLUMN CHROMATOGRAPHY Column ch
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2.3.A.2 STEP-BY-STEP PROCEDURES Fig
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Figure 2.55: a) Jostling the column
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16.Gently rinse the sides of the co
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Figure 2.60: a) Elution, b) Additio
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Figure 2.63: a) Eluted TLC plates o
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2.3.A.3 MACROSCALE COLUMN SUMMARY M
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2.3.A.4 C THE BANDS ARE ELUTING UNE
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4. Gently clamp the pipette column
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Elute the Column and Collect Fracti
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2.4 GAS CHROMATOGRAPHY (GC) 2.4.A O
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2.4.B.2 IDENTIFYING COMPONENTS Due
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IMF’s with the column coating spe
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2.4.D QUANTITATING WITH GC 2.4.D.1
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2.4.D.2 USING A CALIBRATION CURVE O
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2.4.E GC PARAMETERS There are many
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2.4.E.3 OVEN TEMPERATURE The temper
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2.4.F SAMPLE PREPARATION Liquid GC
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CHAPTER 3 CRYSTALLIZATION Time-laps
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3.1 OVERVIEW OF CRYSTALLIZATION In
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To demonstrate, a mixture containin
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3.3.B GENERAL PROCEDURES FOR REMOVI
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3.3.D USING SOLUBILITY DATA If you
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3.3.F MIXED SOLVENTS When no single
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3.4 CRYSTALLIZATION THEORY 3.4.A PU
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3.4.C USING THE MINIMUM AMOUNT OF H
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To demonstrate the importance of us
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3.4.E QUANTITATING CRYSTALLIZATION
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3.4.E.2 WITH AN IMPURITY OF SIMILAR
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A “second crop” solid should al
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3.5 PROCEDURAL GENERALITIES 3.5.A G
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3.5.C CHARCOAL Activated charcoal i
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3.5.D COOLING SLOWLY After a soluti
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There are a few others methods that
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Figure 3.50: a) Impure NBS added to
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Figure 3.53: a-c) Cooling and cryst
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3.6.C USING SOLVENTS OTHER THAN WAT
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3.6.D MIXED SOLVENT CRYSTALLIZATION
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3.6.E MIXED SOLVENT SUMMARY Find a
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3.6.F.2 CRYSTALLIZATION DOESN’T H
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3.6.F.4 LIQUID DROPLETS FORM (THE S
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CHAPTER 4 EXTRACTION Organic solven
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4.1 OVERVIEW OF EXTRACTION “Extra
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4.2.C SELECTIVE REMOVAL OF COMPONEN
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4.3.B HOW TO DETERMINE THE AQUEOUS
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4.4.B CHOOSING A SOLVENT WITH SOLUB
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4.4.D MULTIPLE EXTRACTIONS 4.4.D.1
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4.4.D.2 QUANTITATING MULTIPLE EXTRA
Page 215 and 216:
4.5 STEP-BY-STEP PROCEDURES 4.5.A S
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Figure 4.24: a) Closed and open sto
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Figure 4.27: a) Taking the stopper
Page 221 and 222:
4.5.B SINGLE EXTRACTION SUMMARY Use
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If the organic layer (incorrect) wa
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4.5.D TROUBLESHOOTING This section
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Figure 4.34: a) An emulsion with bi
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3. Gently mix the two solutions usi
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O + cat. H 2 SO 4 O OH HO O acetic
Page 233 and 234:
Testing the pH After a Wash To test
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If drying agents are used to remove
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4.6.C DRYING AGENTS 4.6.C.1 WHY THE
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In some procedures Na 2 SO 4 or CaC
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Figure 4.53: a) Wet hydrate of Na 2
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4.7.B SODIUM BICARBONATE WASHES An
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4.7.C.3 EXTRACTING ACID, BASE, AND
Page 247 and 248:
CHAPTER 5 DISTILLATION Steam distil
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5.1 OVERVIEW OF DISTILLATION Distil
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5.2 SIMPLE DISTILLATION 5.2.A USES
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Figure 5.7: a) Benzaldehyde reagent
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5.2.B.2 PURIFICATION POTENTIAL A si
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In this distillation, the differenc
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Every mixture has its own distillat
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Figure 5.15: a) Distillation curve
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Azeotropic mixtures come in two for
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5.2.C.2 SIMPLE DISTILLATION PROCEDU
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5. Attach a three-way adapter (or
Page 269 and 270:
15.A completed distillation apparat
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The thermometer bulb must be fully
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5.2.C.4 VARIATIONS A few variations
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If glass wool is unavailable, alumi
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5.2.D.3 SHORT-PATH DISTILLATION An
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The concepts of a fractional distil
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5.3.C USES OF FRACTIONAL DISTILLATI
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Figure 5.44: a) Removal of glass wo
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5.4 VACUUM DISTILLATION 5.4.A OVERV
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5.4.C STEP-BY-STEP PROCEDURES 5.4.C
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Figure 5.52: a) Stir plate with woo
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5.4.C.2 VACUUM DISTILLATION SUMMARY
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5.5.C SEPARATION THEORY Although st
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Figure 5.59: Steam distillation var
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Figure 5.62: a+b) Distillate with o
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5.5.D.2 STEAM DISTILLATION SUMMARY
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5.6.B STEP-BY-STEP PROCEDURES 5.6.B
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. If the expected compound is a liq
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5.6.C TROUBLESHOOTING 1. If the sol
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CHAPTER 6 MISCELLANEOUS TECHNIQUES
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6.1 MELTING POINT 6.1.A OVERVIEW OF
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6.1.B.2 ASSESSING PURITY A second r
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6.1.C MELTING POINT THEORY 6.1.C.1
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6.1.C.2.B BROADENING OF THE MELTING
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6.1.D.2 MELTING POINT APPARATUS Fig
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. The sample may sublime instead of
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7. If the expected melting point of
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6.1.E MIXED MELTING POINTS As previ
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6.2.B.2 REFLUX METHOD A reflux setu
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6.2.B.3.B THIELE TUBE PROCEDURE Fig
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6.2.B.3.C THIELE TUBE SUMMARY Fill
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6.3.A OVERVIEW OF SUBLIMATION Some
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Figure 6.31: Time-lapse sublimation
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Figure 6.34: a) Small scale sublima
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6.3.B.3 VACUUM SUBLIMATION SUMMARY
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6.4.B FLOWCHARTS In some teaching l
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3. Unsaturated Hydrocarbons (Alkene
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Permanganate (Baeyer) Test pH Test
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6.4.D.2 BENEDICT’S TEST The Bened
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6.4.D.3 BICARBONATE TEST Carboxylic
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6.4.D.5 CHROMIC ACID (JONES) TEST A
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6.4.D.7 FERRIC HYDROXAMATE TEST The
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6.4.D.9 LUCAS TEST The Lucas Reagen
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6.4.D.11 pH TEST Carboxylic acids a
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6.4.D.13 SILVER NITRATE TEST A dilu
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6.4.D.15 TOLLENS TEST The Tollens r
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CHAPTER 7 SUMMARIES 7.1 Flame-Dryin
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7.2 USING CALIBRATED GLASS PIPETTES
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7.4 REFLUX Pour liquid into the fla
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7.6 HOT FILTRATION Prepare a fluted
Page 369 and 370:
7.8 TLC VISUALIZATION METHODS Ultra
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7.10 PIPETTE COLUMN CHROMATOGRAPHY
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7.12 TESTING MIXED SOLVENTS FOR CRY
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7.14 MIXED SOLVENT CRYSTALLIZATION
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7.16 MULTIPLE EXTRACTIONS Organic l
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7.18 TESTING THE pH AFTER A WASH If
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7.20 ACID-BASE EXTRACTION a) Extrac
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7.22 FRACTIONAL DISTILLATION Figure
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7.24 STEAM DISTILLATION Figure 7.12
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7.26 MELTING POINTS Load the sample
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7.28 VACUUM SUBLIMATION Figure 7.14
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