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Microscale Techniques for the Organic Laboratory, 2nd Edition
by
Mayo, Dana W., Bowdoin College; Pike, Ronald M., Merrimack College; Trumper, Peter K., Univ. of Maine School of Law
Publisher: John Wiley & Sons
Publishing Date: 2001/06/29
eText ISBN-10
0-470-26630-9
eText ISBN-13
978-0-470-26630-4
Print ISBN-10
0-471-24909-2
Print ISBN-13
978-0-471-24909-2
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Microscale Techniques for the Organic Laboratory, 2nd Edition
by
Mayo, Dana W., Bowdoin College; Pike, Ronald M., Merrimack College; Trumper, Peter K., Univ. of Maine School of Law
eTextbook $39.50
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Copyright, iv
Preface, vii
Chapter 1. Introduction, ...
Chapter 2. Safety, 6
Chapter 3. Introduction t...
Chapter 4. Determination ...
Chapter 5. Microscale Lab...
Chapter 6.
TECHNIQUE 10:
...
Chapter 7.
TECHNIQUE 11:
...
Chapter 8.
TECHNIQUE 12:
...
Chapter 9.
TECHNIQUE 13:
...
Chapter 10. Qualitative I...
Glossary, 303
Index, 307
Table of Contents
Copyright, iv
Preface, vii
Chapter 1. Introduction, 1
General Rules for the Microscale Laboratory, 3
The Organic Chemistry Laboratory, 4
Chapter 2. Safety, 6
Making the Laboratory a Safer Place, 6
Nature of Hazards
, 7
Reduction of Risks
, 7
Precautionary Measures
, 9
Thinking about the Risks in Using Chemicals, 9
Disposal of Chemicals
, 10
Material Safety Data Sheets
, 10
Alternate Sources of Information
, 14
Estimating the Risks from Vapors
, 14
Concluding Thoughts
, 16
Chapter 3. Introduction to Microscale Organic Laboratory Equipment and Techniques, 19
Microglassware Equipment, 20
Standard Taper Joints
, 20
Conical Vials
, 22
Condensers
, 22
Distillation Heads
, 22
Recrystallization Tubes
, 22
Miscellaneous Items
, 23
Gas Chromatographic Fraction Collection Items
, 23
Standard Experimental Apparatus, 23
Heating and Stirring Arrangements
, 23
Sand Bath Technique/Hotplate Calibration
, 23
Metal Heat-Transfer Devices
, 25
Stirring
, 25
Reflux Apparatus, 25
Distillation Apparatus, 27
Moisture-Protected Reaction Apparatus, 29
Specialized Pieces of Equipment, 30
Microscale Laws, 32
Rules of the Trade for Handling Organic Materials at the Microscale Level
, 32
Rules for Working with Liquids at the Microscale Level
, 32
Rules for Working with Solids at the Microscale Level
, 36
The Laboratory Notebook, 36
Example of a Laboratory Notebook Entry, 38
Calculation of Yields, 40
Chapter 4. Determination of Physical Properties, 42
Liquids, 43
Ultramicro-Boiling Point, 43
Density, 47
Refractive Index, 49
Solids, 52
Melting Points, 52
Simple Capillary Melting Point
, 52
Evacuated Melting Points
, 53
Mixture Melting Points
, 55
Chapter 5. Microscale Laboratory Techniques, 57
TECHNIQUE 1:
Microscale Separation of Liquid Mixtures by Preparative Gas Chromatography, 57
GC Instrumentation, 58
Procedure for Preparative Collection, 62
EXAMPLE [1A]: The Separation of a 25-μL Mixture of Heptanol (bp 153 °C) and Cyclohexanol (bp 160 °C) by Gas Chromatography, 64
EXAMPLE [1B]: The Separation of a 40-μL Mixture of (1
S
)-(–)–-α- Pinene (bp 156 °C) and (1
S
)-(–)– -β-Pinene (bp 165 °C) by Gas Chromatography, 69
EXAMPLE [1C]: The Separation of a 40-μL Mixture of 2-Heptanone (bp 149-150 °C) and Cyclohexanol (bp 160-161 °C) by Gas Chromatography, 70
EXAMPLE [1D]: The Separation of a 40-μL Mixture of
d
-Limonene (bp 175-176 °C) and Cyclohexyl acetate (bp 173 °C) by Gas Chromatography, 70
TECHNIQUES 2
and
3:
Distillation, 72
TECHNIQUE 2:
Simple Distillation at the Semimicroscale Level, 73
EXAMPLE [2A]: Simple Semimicroscale Distillation: Separation of Hexane and Toluene, 76
TECHNIQUE 3:
Fractional Semimicroscale Distillation, 79
EXAMPLE [3A]: Fractional Semimicroscale Distillation: Separation of 2-Methylpentane and Cyclohexane Using a Spinning-Band Column, 83
EXAMPLE [3B]: Fractional Semimicroscale Distillation: Separation of 2-Methylpentane and Cyclohexane Using a Spinning-Band in a Hickman-Hinkle Still, 87
TECHNIQUE 4:
Solvent Extraction, 90
Solubility, 90
Partition Coefficient, 94
Extraction, 96
Liquid–Liquid Extraction, 96
Microscale Extraction, 96
Separatory Funnel—Semimicroscale Macroscale Extraction, 100
Continuous Liquid-Liquid Extraction, 101
Separation of Acids and Bases, 102
Salting Out, 104
Solid–Liquid Extraction, 104
Drying Agents, 106
Solid-Phase Extraction, 108
TECHNIQUE 5:
Crystallization, 110
General Crystallization Procedure, 111
Simple Crystallization, 112
Filtration Techniques, 113
Use of the Hirsch Funnel, 113
A Hirsch Funnel Alternative—Nail-filter Funnel, 116
Craig Tube Crystallizations, 116
TECHNIQUE 6:
Chromatography, 119
TECHNIQUE 6A:
Column, Flash, High-Performance, Liquid, Paper, and Thin-Layer Chromatography, 119
Column Chromatography, 119
Packing the Column, 120
Sample Application, 121
Elution of the Column, 122
Fraction Collection, 123
Flash Chromatography, 123
Thin-Layer Chromatography, 125
Paper Chromatography, 128
High-Performance Liquid Chromatography, 128
TECHNIQUE 6B:
Concentration of Solutions, 130
Distillation, 130
Evaporation with Nitrogen Gas, 130
Removal of Solvent Under Reduced Pressure, 131
TECHNIQUE 7:
Collection and Control of Gaseous Products, 134
Water Insoluble Gases, 134
Trapping Byproduct Gases, 135
TECHNIQUE 8:
Measurement Of Specific Rotation, 137
Theory, 137
The Polarimeter, 139
Inaccurate Measurements, 141
High-Performance Polarimeters and Optical Rotary Dispersion, 141
Applications to Structure Determination in Natural Products, 141
TECHNIQUE 9:
Sublimation, 142
Sublimation Theory, 143
Experimental Set-up, 143
Precautions, 144
Chapter 6.
TECHNIQUE 10:
Introduction to Infrared Spectroscopy, 146
Introduction to Group Frequencies: Interpretation of Infrared Spectra, 148
Strategies for Interpreting Infrared Spectra, 149
A Survey of Group Frequencies Identified in Organic Molecules, 150
Group Frequencies of the Hydrocarbons
, 151
Alkanes, 151
Alkenes C═C Stretching, 153
Alkene C—H, 153
Alkynes, 153
Arenes, 154
Group Frequencies of Carbonyl Groups
, 154
Factors that Raise the C═O Frequency, 154
Factors that Lower the C═O Frequency, 155
Group Frequencies of the Heteroatom Functional Groups
, 156
Hexane, 156
Alcohols, 156
Aldehydes, 157
Ketones, 157
Esters, 157
Acyl Halides, 157
Carboxylic Acids, 157
Anhydrides, 158
Ethers, 159
Primary Amines, 159
Nitriles, 159
Primary Amides, 159
Secondary Amides, 160
Isocyanates, 161
Thiols, 161
Alkyl Halides, 161
Aryl Halides (Chlorobenzene), 162
Infrared Spectroscopy: Instrumentation and Sample Handling, 162
Instrumentation, 162
Sample Handling in the Infrared, 163
Liquid Samples, 163
Solution Spectra and Spectra of Materials Boiling Below 100 °C, 164
Solid Samples, 164
Infrared Analysis: Reduction of Ketones Using a Metal Hydride Reagent: Cyclohexanone to Cyclohexanol, 166
A Spectral Comparison of Reactant and Product, 166
Infrared Analysis: An Additional Example of the Reduction of t-Butylcyclohexanone, 168
Chapter 7.
TECHNIQUE 11:
Introduction to Nuclear Magnetic Resonance Spectroscopy:, 179
Nuclear Spin, 179
Instrumentation, 180
Chemical Shift, 183
Spin-Spin Coupling, 184
Intensities, 188
Second-Order Effects, 188
Interpretation of
1
H NMR Spectra, 189
1
H Chemical Shifts, 192
Spin-Spin Coupling, 194
Geminal Coupling, 194
Vicinal Coupling, 194
Long-Range Coupling, 195
Examples of Complex, Yet First-Order, Coupling, 196
Ethyl Vinyl Ether, 196
Allyl Acetate, 198
4-
tert
-Butylcyclohexanol, 201
13
C NMR Spectroscopy, 203
Two-Dimensional Nuclear Magnetic Resonance Spectroscopy, 209
Nuclear Magnetic Resonance Spectroscopy Sampling, 212
Chapter 8.
TECHNIQUE 12:
Introduction to Ultraviolet-Visible Spectroscopy Absorption Spectroscopy: Theory, 218
UV-Vis Spectroscopy, 220
Applications to Organic Molecules, 222
Instrumentation, 231
Sample Preparation, 234
Chapter 9.
TECHNIQUE 13:
Introduction to Mass Spectrometry, 237
Instrumentation
, 240
Ion Source, 240
Mass Analyzer, 241
Detector, 243
Tuning the Mass Spectrometer, 244
Sample Introduction, 244
Gas Chromatography/Mass Spectrometry, 245
Capillary Columns, 245
Split Injection, 246
Split/Splitless Injection, 246
Features of the Mass Spectrum
, 248
Terms, 248
Isotope Peaks, 248
Recognizing the Molecular Ion, 249
Mass Spectral Interpretation, 252
Case Study: Synthesis of Methyl Benzoate
, 253
Chapter 10. Qualitative Identification of Organic Compounds, 259
Organic Qualitative Analysis, 259
Preliminary Tests, 261
Separation of Impurities, 264
Detection of Elements Other Than Carbon, Hydrogen, and Oxygen, 264
Solubility Characteristics, 270
The Classification Tests, 272
Preparation of Derivatives, 289
Carboxylic Acids, 290
Alcohols, 292
Aldehydes and Ketones, 294
Amines, 295
Acid Chlorides and Anhydrides, 296
Aromatic Hydrocarbons, 297
Nitriles, 297
Phenols, 298
Aliphatic Hydrocarbons, Halogenated, Hydrocarbons, Amides, Nitro Compounds, Ethers, and Esters, 298
Glossary, 303
Index, 307
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