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EBOOK - A Small Scale Approach to Organic Laboratory Techniques (Donald L. Pavia)
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The purpose of this lab book is to teach students the techniques of organic chemistry. We desire to share our love of the organic chemistry lab and the joy it brings us with our students! In this edition, we have provided many new, up-to-date experi-ments that will demonstrate how organic chemistry is evolving. We have updated and improved many of the standard experiments from previous editions, and we have added some new ones.
For example, we have included some experiments in-volving dyes. For fun, we have added a project experiment that asks the students to formulate a paint and then use it in an art project. We think that you will be en-thusiastic about this new edition. Many of the new experiments will not be found in other laboratory manuals, but we have been careful to retain all of the standard reactions and techniques, such as the Friedel-Crafts reaction, aldol condensation, Grignard synthesis, and basic experiments designed to teach crystallization, chro-matography, and distillation.
CONTENTS:
p A r T 1
Introduction to Basic Laboratory Techniques 1
1 Solubility 2
2 Crystallization 9
2A Macroscale Crystallization 11
2B Selecting a Solvent to Crystallize a Substance 13
2c Mixture Melting Points 14
2D Critical-Thinking Application 14
3 Extraction 18
3A Extraction of Caffeine 19
3B Distribution of a Solute between Two Immiscible Solvents 20
3c How Do You Determine Which One Is the Organic Layer? 22
3D Use of Extraction to Isolate a Neutral Compound
from a Mixture Containing an Acid or Base Impurity 22
3e Critical-Thinking Application 25
4 A Separation and Purification Scheme 27
4A Extractions with a Separatory Funnel 28
4B Extractions with a Screw-Cap Centrifuge Tube 29
5 Chromatography 30
5A Thin-Layer Chromatography 31
5B Selecting the Correct Solvent for Thin-Layer Chromatography 33
5c Monitoring a Reaction with Thin-Layer Chromatography 34
5D Column Chromatography 35
6 Simple and Fractional Distillation 38
7 Infrared Spectroscopy and Boiling-Point Determination 43
essay Aspirin 47
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
xii Contents
8 Acetylsalicylic Acid 50
essay Analgesics 53
9 Acetaminophen 57
essay Identification of Drugs 60
10 TLC Analysis of Analgesic Drugs 62
essay Caffeine 67
11 Isolation of Caffeine from Tea Leaves 70
11A Isolation of Caffeine from Tea Leaves 73
11B Isolation of Caffeine from a Tea Bag 75
essay Esters—Flavors and Fragrances 77
12 Isopentyl Acetate (Banana Oil) 81
essay Terpenes and Phenylpropanoids 84
13 Isolation of Eugenol from Cloves 88
essay Stereochemical Theory of Odor 91
14 Spearmint and Caraway Oil: (+)-and (–)-Carvones 96
essay The Chemistry of Vision 104
15 Isolation of Chlorophyll and Carotenoid Pigments from Spinach 109
essay Ethanol and Fermentation Chemistry 116
16 Ethanol from Sucrose 119
p A r T 2
Introduction to Molecular Modeling 125
essay Molecular Modeling and Molecular Mechanics 126
17 An Introduction to Molecular Modeling 130
17A The Conformations of n-Butane: Local Minima 131
17B Cyclohexane Chair and Boat Conformations 132
17c Substituted Cyclohexane Rings (Critical Thinking Exercises) 133
17D cis- and trans-2-Butene 134
essay Computational Chemistry—ab Initio and Semiempirical Methods 135
18 Computational Chemistry 143
18A Heats of Formation: Isomerism, Tautomerism, and Regioselectivity 144
18B Heats of Reaction: SN1 Reaction Rates 146
18c Density–Electrostatic Potential Maps: Acidities of Carboxylic Acids 147
18D Density–Electrostatic Potential Maps: Carbocations 147
18e Density–LUMO Maps: Reactivities of Carbonyl Groups 148
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Contents xiii
p A r T 3
Properties and Reactions of Organic Compounds 151
19 Reactivities of Some Alkyl Halides 152
20 Nucleophilic Substitution Reactions: Competing Nucleophiles 156
20A Competing Nucleophiles with 1-Butanol or 2-Butanol 159
20B Competing Nucleophiles with 2-Methyl-2-Propanol 161
20c Analysis 162
21 Synthesis of n-Butyl Bromide and t-Pentyl Chloride 165
21A n-Butyl Bromide 167
21B t-Pentyl Chloride 169
22 4-Methylcyclohexene 171
essay Fats and Oils 175
23 Methyl Stearate from Methyl Oleate 181
essay Soap 186
24 Preparation of Soap 190
24A Preparation of Soap from 70% Lard and 30% Coconut Oil 192
24B Preparation of Several Soaps with a Given % Composition 194
essay Petroleum and Fossil Fuels 196
25 Gas-Chromatographic Analysis of Gasolines 205
essay Biofuels 209
26 Biodiesel 213
26A Biodiesel from Coconut Oil 215
26B Biodiesel from Other Oils 216
26c Analysis of Biodiesel 216
essay Green Chemistry 218
27 Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination 224
27A Chiral Reduction of Ethyl Acetoacetate 225
27B NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate 228
28 Nitration of Aromatic Compounds Using a Recyclable Catalyst 234
29 Reduction of Ketones Using Carrots as Biological Reducing Agents 238
30 Resolution of (6)-a-Phenylethylamine and Determination of Optical Purity 240
30A Resolution of (6)-a-Phenylethylamine 243
30B Determination of Optical Purity Using NMR and a Chiral Resolving Agent 246
31 An Oxidation–Reduction Scheme: Borneol, Camphor, Isoborneol 248
32 Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid 262
32A Preparation of Benzoin by Thiamine Catalysis 263
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
xiv Contents
32B Preparation of Benzil 269
32c Preparation of Benzilic Acid 271
33 Triphenylmethanol and Benzoic Acid 274
33A Triphenylmethanol 281
33B Benzoic Acid 283
34 Aqueous-Based Organozinc Reactions 286
35 Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium
Catalyst 289
36 Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product 299
37 The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones) 306
38 A Green Enantioselective Aldol Condensation Reaction 310
39 Preparation of an a, b-Unsaturated Ketone via Michael and Aldol Condensation Reactions 317
40 Preparation of Triphenylpyridine 321
41 1,4-Diphenyl-1,3-Butadiene 324
42 Relative Reactivities of Several Aromatic Compounds 330
43 Nitration of Methyl Benzoate 335
essay Synthetic Dyes 340
44 Preparation of Methyl Orange 345
45 Preparation of Indigo 349
46 Formulation of a Paint and Art Project 352
essay Local Anesthetics 354
47 Benzocaine 358
essay Pheromones: Insect Attractants and Repellents 361
48 N,N-Diethyl-m-toluamide: The Insect Repellent “OFF” 369
essay Sulfa Drugs 374
49 Sulfa Drugs: Preparation of Sulfanilamide 377
essay Polymers and Plastics 382
50 Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene 393
50A Polyesters 394
50B Polyamide (Nylon) 396
50c Polystyrene 397
50D Infrared Spectra of Polymer Samples 399
51 Ring-Opening Metathesis Polymerization (ROMP) Using a Grubbs Catalyst: A Three-Step Synthesis
of a Polymer 401
51A Diels-Alder Reaction 404
51B Conversion of the Diels-Alder Adduct to the Diester 405
51c Synthesizing a Polymer by Ring-Opening Metathesis Polymerization (ROMP) 407
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Contents xv
essay Diels–Alder Reaction and Insecticides 411
52 The Diels–Alder Reaction of Cyclopentadiene with Maleic Anhydride 416
53 The Diels-Alder Reaction with Anthracene-9-Methanol 421
54 Photoreduction of Benzophenone and Rearrangement of Benzopinacol to
Benzopinacolone 423
54A Photoreduction of Benzophenone 424
54B Synthesis of b-Benzopinacolone: The Acid-Catalyzed Rearrangement
of Benzopinacol 431
essay Fireflies and Photochemistry 433
55 Luminol 436
essay The Chemistry of Sweeteners 440
56 Carbohydrates 445
57 Analysis of a Diet Soft Drink by HPLC 454
p A r T 4
Identification of Organic Substances 457
58 Identification of Unknowns 458
58A Solubility Tests 465
58B Tests for the Elements (N, S, X) 472
58c Tests for Unsaturation 478
58D Aldehydes and Ketones 482
58e Carboxylic Acids 488
58F Phenols 490
58G Amines 493
58h Alcohols 497
58I Esters 501
p A r T 5
Project-Based Experiments 505
59 Preparation of a C-4 or C-5 Acetate Ester 506
60 Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using
2-Pentanol and 3-Pentanol 509
61 Friedel–Crafts Acylation 514
62 The Analysis of Antihistamine Drugs by Gas Chromatography–Mass Spectrometry 521
63 Carbonation of an Unknown Aromatic Halide 523
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
xvi Contents
64 The Aldehyde Enigma 526
65 Synthesis of Substituted Chalcones: A Guided-Inquiry Experience 528
66 Green Epoxidation of Chalcones 533
67 Cyclopropanation of Chalcones 537
68 Michael and Aldol Condensation Reactions 540
69 Esterification Reactions of Vanillin: The Use of NMR to Determine a Structure 544
p A r T 6
The Techniques 547
1 Laboratory Safety 548
2 The Laboratory Notebook, Calculations, and Laboratory Records 566
3 Laboratory Glassware: Care and Cleaning 573
4 How to Find Data for Compounds: Handbooks and Catalogs 581
5 Measurement of Volume and Weight 588
6 Heating and Cooling Methods 600
7 Reaction Methods 610
8 Filtration 632
9 Physical Constants of Solids: The Melting Point 645
10 Solubility 655
11 Crystallization: Purification of Solids 664
12 Extractions, Separations, and Drying Agents 683
13 Physical Constants of Liquids: The Boiling Point and Density 711
14 Simple Distillation 722
15 Fractional Distillation, Azeotropes 733
16 Vacuum Distillation, Manometers 752
17 Sublimation 766
18 Steam Distillation 773
19 Column Chromatography 780
20 Thin-Layer Chromatography 804
21 High-Performance Liquid Chromatography (HPLC) 815
22 Gas Chromatography 820
23 Polarimetry 840
24 Refractometry 848
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Contents xvii
25 Infrared Spectroscopy 854
26 Nuclear Magnetic Resonance Spectroscopy (Proton NMR) 888
27 Carbon-13 Nuclear Magnetic Resonance Spectroscopy 929
28 Mass Spectrometry 946
29 Guide to the Chemical Literature 964
A ppe NDI ces 979
1 Tables of Unknowns and Derivatives 980
2 Procedures for Preparing Derivatives 994
3 Index of Spectra 998
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The purpose of this lab book is to teach students the techniques of organic chemistry. We desire to share our love of the organic chemistry lab and the joy it brings us with our students! In this edition, we have provided many new, up-to-date experi-ments that will demonstrate how organic chemistry is evolving. We have updated and improved many of the standard experiments from previous editions, and we have added some new ones.
For example, we have included some experiments in-volving dyes. For fun, we have added a project experiment that asks the students to formulate a paint and then use it in an art project. We think that you will be en-thusiastic about this new edition. Many of the new experiments will not be found in other laboratory manuals, but we have been careful to retain all of the standard reactions and techniques, such as the Friedel-Crafts reaction, aldol condensation, Grignard synthesis, and basic experiments designed to teach crystallization, chro-matography, and distillation.
CONTENTS:
p A r T 1
Introduction to Basic Laboratory Techniques 1
1 Solubility 2
2 Crystallization 9
2A Macroscale Crystallization 11
2B Selecting a Solvent to Crystallize a Substance 13
2c Mixture Melting Points 14
2D Critical-Thinking Application 14
3 Extraction 18
3A Extraction of Caffeine 19
3B Distribution of a Solute between Two Immiscible Solvents 20
3c How Do You Determine Which One Is the Organic Layer? 22
3D Use of Extraction to Isolate a Neutral Compound
from a Mixture Containing an Acid or Base Impurity 22
3e Critical-Thinking Application 25
4 A Separation and Purification Scheme 27
4A Extractions with a Separatory Funnel 28
4B Extractions with a Screw-Cap Centrifuge Tube 29
5 Chromatography 30
5A Thin-Layer Chromatography 31
5B Selecting the Correct Solvent for Thin-Layer Chromatography 33
5c Monitoring a Reaction with Thin-Layer Chromatography 34
5D Column Chromatography 35
6 Simple and Fractional Distillation 38
7 Infrared Spectroscopy and Boiling-Point Determination 43
essay Aspirin 47
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
xii Contents
8 Acetylsalicylic Acid 50
essay Analgesics 53
9 Acetaminophen 57
essay Identification of Drugs 60
10 TLC Analysis of Analgesic Drugs 62
essay Caffeine 67
11 Isolation of Caffeine from Tea Leaves 70
11A Isolation of Caffeine from Tea Leaves 73
11B Isolation of Caffeine from a Tea Bag 75
essay Esters—Flavors and Fragrances 77
12 Isopentyl Acetate (Banana Oil) 81
essay Terpenes and Phenylpropanoids 84
13 Isolation of Eugenol from Cloves 88
essay Stereochemical Theory of Odor 91
14 Spearmint and Caraway Oil: (+)-and (–)-Carvones 96
essay The Chemistry of Vision 104
15 Isolation of Chlorophyll and Carotenoid Pigments from Spinach 109
essay Ethanol and Fermentation Chemistry 116
16 Ethanol from Sucrose 119
p A r T 2
Introduction to Molecular Modeling 125
essay Molecular Modeling and Molecular Mechanics 126
17 An Introduction to Molecular Modeling 130
17A The Conformations of n-Butane: Local Minima 131
17B Cyclohexane Chair and Boat Conformations 132
17c Substituted Cyclohexane Rings (Critical Thinking Exercises) 133
17D cis- and trans-2-Butene 134
essay Computational Chemistry—ab Initio and Semiempirical Methods 135
18 Computational Chemistry 143
18A Heats of Formation: Isomerism, Tautomerism, and Regioselectivity 144
18B Heats of Reaction: SN1 Reaction Rates 146
18c Density–Electrostatic Potential Maps: Acidities of Carboxylic Acids 147
18D Density–Electrostatic Potential Maps: Carbocations 147
18e Density–LUMO Maps: Reactivities of Carbonyl Groups 148
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Contents xiii
p A r T 3
Properties and Reactions of Organic Compounds 151
19 Reactivities of Some Alkyl Halides 152
20 Nucleophilic Substitution Reactions: Competing Nucleophiles 156
20A Competing Nucleophiles with 1-Butanol or 2-Butanol 159
20B Competing Nucleophiles with 2-Methyl-2-Propanol 161
20c Analysis 162
21 Synthesis of n-Butyl Bromide and t-Pentyl Chloride 165
21A n-Butyl Bromide 167
21B t-Pentyl Chloride 169
22 4-Methylcyclohexene 171
essay Fats and Oils 175
23 Methyl Stearate from Methyl Oleate 181
essay Soap 186
24 Preparation of Soap 190
24A Preparation of Soap from 70% Lard and 30% Coconut Oil 192
24B Preparation of Several Soaps with a Given % Composition 194
essay Petroleum and Fossil Fuels 196
25 Gas-Chromatographic Analysis of Gasolines 205
essay Biofuels 209
26 Biodiesel 213
26A Biodiesel from Coconut Oil 215
26B Biodiesel from Other Oils 216
26c Analysis of Biodiesel 216
essay Green Chemistry 218
27 Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination 224
27A Chiral Reduction of Ethyl Acetoacetate 225
27B NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate 228
28 Nitration of Aromatic Compounds Using a Recyclable Catalyst 234
29 Reduction of Ketones Using Carrots as Biological Reducing Agents 238
30 Resolution of (6)-a-Phenylethylamine and Determination of Optical Purity 240
30A Resolution of (6)-a-Phenylethylamine 243
30B Determination of Optical Purity Using NMR and a Chiral Resolving Agent 246
31 An Oxidation–Reduction Scheme: Borneol, Camphor, Isoborneol 248
32 Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid 262
32A Preparation of Benzoin by Thiamine Catalysis 263
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
xiv Contents
32B Preparation of Benzil 269
32c Preparation of Benzilic Acid 271
33 Triphenylmethanol and Benzoic Acid 274
33A Triphenylmethanol 281
33B Benzoic Acid 283
34 Aqueous-Based Organozinc Reactions 286
35 Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium
Catalyst 289
36 Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product 299
37 The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones) 306
38 A Green Enantioselective Aldol Condensation Reaction 310
39 Preparation of an a, b-Unsaturated Ketone via Michael and Aldol Condensation Reactions 317
40 Preparation of Triphenylpyridine 321
41 1,4-Diphenyl-1,3-Butadiene 324
42 Relative Reactivities of Several Aromatic Compounds 330
43 Nitration of Methyl Benzoate 335
essay Synthetic Dyes 340
44 Preparation of Methyl Orange 345
45 Preparation of Indigo 349
46 Formulation of a Paint and Art Project 352
essay Local Anesthetics 354
47 Benzocaine 358
essay Pheromones: Insect Attractants and Repellents 361
48 N,N-Diethyl-m-toluamide: The Insect Repellent “OFF” 369
essay Sulfa Drugs 374
49 Sulfa Drugs: Preparation of Sulfanilamide 377
essay Polymers and Plastics 382
50 Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene 393
50A Polyesters 394
50B Polyamide (Nylon) 396
50c Polystyrene 397
50D Infrared Spectra of Polymer Samples 399
51 Ring-Opening Metathesis Polymerization (ROMP) Using a Grubbs Catalyst: A Three-Step Synthesis
of a Polymer 401
51A Diels-Alder Reaction 404
51B Conversion of the Diels-Alder Adduct to the Diester 405
51c Synthesizing a Polymer by Ring-Opening Metathesis Polymerization (ROMP) 407
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Contents xv
essay Diels–Alder Reaction and Insecticides 411
52 The Diels–Alder Reaction of Cyclopentadiene with Maleic Anhydride 416
53 The Diels-Alder Reaction with Anthracene-9-Methanol 421
54 Photoreduction of Benzophenone and Rearrangement of Benzopinacol to
Benzopinacolone 423
54A Photoreduction of Benzophenone 424
54B Synthesis of b-Benzopinacolone: The Acid-Catalyzed Rearrangement
of Benzopinacol 431
essay Fireflies and Photochemistry 433
55 Luminol 436
essay The Chemistry of Sweeteners 440
56 Carbohydrates 445
57 Analysis of a Diet Soft Drink by HPLC 454
p A r T 4
Identification of Organic Substances 457
58 Identification of Unknowns 458
58A Solubility Tests 465
58B Tests for the Elements (N, S, X) 472
58c Tests for Unsaturation 478
58D Aldehydes and Ketones 482
58e Carboxylic Acids 488
58F Phenols 490
58G Amines 493
58h Alcohols 497
58I Esters 501
p A r T 5
Project-Based Experiments 505
59 Preparation of a C-4 or C-5 Acetate Ester 506
60 Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using
2-Pentanol and 3-Pentanol 509
61 Friedel–Crafts Acylation 514
62 The Analysis of Antihistamine Drugs by Gas Chromatography–Mass Spectrometry 521
63 Carbonation of an Unknown Aromatic Halide 523
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
xvi Contents
64 The Aldehyde Enigma 526
65 Synthesis of Substituted Chalcones: A Guided-Inquiry Experience 528
66 Green Epoxidation of Chalcones 533
67 Cyclopropanation of Chalcones 537
68 Michael and Aldol Condensation Reactions 540
69 Esterification Reactions of Vanillin: The Use of NMR to Determine a Structure 544
p A r T 6
The Techniques 547
1 Laboratory Safety 548
2 The Laboratory Notebook, Calculations, and Laboratory Records 566
3 Laboratory Glassware: Care and Cleaning 573
4 How to Find Data for Compounds: Handbooks and Catalogs 581
5 Measurement of Volume and Weight 588
6 Heating and Cooling Methods 600
7 Reaction Methods 610
8 Filtration 632
9 Physical Constants of Solids: The Melting Point 645
10 Solubility 655
11 Crystallization: Purification of Solids 664
12 Extractions, Separations, and Drying Agents 683
13 Physical Constants of Liquids: The Boiling Point and Density 711
14 Simple Distillation 722
15 Fractional Distillation, Azeotropes 733
16 Vacuum Distillation, Manometers 752
17 Sublimation 766
18 Steam Distillation 773
19 Column Chromatography 780
20 Thin-Layer Chromatography 804
21 High-Performance Liquid Chromatography (HPLC) 815
22 Gas Chromatography 820
23 Polarimetry 840
24 Refractometry 848
Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Contents xvii
25 Infrared Spectroscopy 854
26 Nuclear Magnetic Resonance Spectroscopy (Proton NMR) 888
27 Carbon-13 Nuclear Magnetic Resonance Spectroscopy 929
28 Mass Spectrometry 946
29 Guide to the Chemical Literature 964
A ppe NDI ces 979
1 Tables of Unknowns and Derivatives 980
2 Procedures for Preparing Derivatives 994
3 Index of Spectra 998
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