Chapter 1 Safety First, Last, and Always 1
Accidents Will Not Happen 5
Disposing of Waste 5
Mixed Waste 7
Material Safety Data Sheet (Msds) 8
Green Chemistry and Planning an Organic Synthesis 8
An iBag for Your iThing 10
Exercises 10
Chapter 2 Keeping a Notebook 11
A Technique Experiment 12
Notebook Notes 12
A Synthesis Experiment 16
Notebook Notes 17
The Six Maybe Seven Elements in Your Experimental Write-Up 20
The Acid Test 21
Notebook Mortal Sin 21
Calculation of Percent Yield (Not Yeild!) 22
Estimation Is Your Friend 24
Exercises 24
Chapter 3 Mining Your Own Data 25
Google and the Wiki 26
The Terphenyl Anomaly 29
Exercises 29
Chapter 4 Jointware 30
Stoppers With Only One Number 31
Another Episode of Love of Laboratory 33
Hall of Blunders and Things Not Quite Right 34
Round-Bottom Flasks 34
Columns and Condensers 34
The Adapter with Lots of Names 35
Forgetting the Glass 36
Inserting Adapter Upside Down 36
Inserting Adapter Upside Down sans Glass 37
The O-Ring and Cap Branch Out 38
Greasing the Joints 38
To Grease or Not to Grease 38
Preparation of the Joints 39
Into the Grease Pit 39
Storing Stuff and Sticking Stoppers 40
Corking a Vessel 40
Chapter 5 Microscale Jointware 41
Microscale: A Few Words 41
Uh-Oh Rings 42
The O-Ring Cap Seal 42
Skinny Apparatus 42
Not-So-Skinny Apparatus 43
Sizing Up the Situation 43
Why I Don’t Really Know How Vacuum-Tight These Seals Are 44
The Comical Vial (That’s Conical!) 45
The Conical Vial as Vial 45
Packaging Oops 46
Tare to the Analytical Balance 46
The Electronic Analytical Balance 46
Heating These Vials 47
The Microscale Drying Tube 48
Gas Collection Apparatus 48
Generating the Gas 49
Isolating the Product 51
Chapter 6 Other Interesting Equipment 52
Funnels, and Beakers, and Flasks—Oh My! 53
The Flexible Double-Ended Stainless Steel Spatula 54
Transferring a Powdered Solid with the Spatula 55
Chapter 7 Pipet Tips 56
Pre-Preparing Pasteur Pipets 56
Calibration 56
Operation 57
Amelioration 58
Pipet Cutting 58
Pipet Filtering—Liquids 60
Pipet Filtering—Solids 61
Chapter 8 Syringes, Needles, and Septa 63
The Rubber Septum 65
Chapter 9 Clean and Dry 66
Drying Your Glassware When You Don’t Need To 67
Drying Your Glassware When You Do Need To 67
Chapter 10 Drying Agents 68
Typical Drying Agents 68
Using a Drying Agent 69
Following Directions and Losing Product Anyway 70
Drying Agents: Microscale 70
Drying in Stages: The Capacity and Efficiency of Drying Agents 70
Exercises 71
Chapter 11 On Products 72
Solid Product Problems 72
Liquid Product Problems 72
The Sample Vial 73
Hold It! Don’t Touch That Vial 73
Chapter 12 The Melting-Point Experiment 74
Sample Preparation 75
Loading the Melting-Point Tube 75
Closing Off Melting-Point Tubes 76
Melting-Point Hints 77
The Mel-Temp Apparatus 77
Operation of the Mel-Temp Apparatus 79
The SRS DigiMelt 80
The Fisher-Johns Apparatus 82
Operation of the Fisher-Johns Apparatus 83
The Thomas-Hoover Apparatus 84
Operation of the Thomas-Hoover Apparatus 85
Using the Thiele Tube 88
Cleaning the Tube 89
Getting the Sample Ready 89
Dunking the Melting-Point Tube 90
Heating the Sample 91
Exercises 91
Chapter 13 Recrystallization 92
Finding a Good Solvent 93
General Guidelines for a Recrystallization 94
My Product Disappeared 95
Gravity Filtration 95
The Buchner Funnel and Filter Flask 97
Just a Note 100
The Hirsch Funnel and Friends 101
Activated Charcoal 101
The Water Aspirator: A Vacuum Source 102
The Water Trap 102
Working with a Mixed-Solvent System—The Good Part 103
The Ethanol—Water System 103
A Mixed-Solvent System—The Bad Part 104
Salting Out 105
World-Famous Fan-Folded Fluted Paper 105
Exercises 107
Chapter 14 Recrystallization: Microscale 108
Isolating the Crystals 109
Craig Tube Filtration 109
Centrifuging the Craig Tube 113
Getting the Crystals Out 113
Chapter 15 Extraction and Washing 114
Never-Ever Land 115
Starting an Extraction 115
Dutch Uncle Advice 116
The Separatory Funnel 117
The Stopper 117
The Teflon Stopcock 118
How to Extract and Wash What 119
The Road to Recovery—Back-Extraction 120
A Sample Extraction 121
Performing an Extraction or Washing 123
Extraction Hints 124
Theory of Extraction 125
Exercises 127
Chapter 16 Extraction and Washing: Microscale 128
Mixing 128
Separation: Removing the Bottom Layer 128
Separation: Removing the Top Layer 129
Separation: Removing Both Layers 130
Chapter 17 Sources of Heat 131
Boiling Stones 131
The Steam Bath 132
The Bunsen Burner 133
Burner Hints 134
The Heating Mantle 135
Proportional Heaters and Stepless Controllers 137
Exercise 139
Chapter 18 Clamps and Clamping 140
Clamping a Distillation Setup 142
Clipping a Distillation Setup 147
CHAPTER 19 Distillation 150
Distillation Notes 151
Class 1: Simple Distillation 151
Sources of Heat 151
The Three-Way Adapter 152
The Distilling Flask 152
The Thermometer Adapter 153
The Ubiquitous Clamp 153
The Thermometer 154
The Condenser 154
The Vacuum Adapter 154
The Receiving Flask 154
The Ice Bath 154
The Distillation Example 155
The Distillation Mistake 155
Class 2: Vacuum Distillation 156
Pressure Measurement 157
Manometer Hints 158
Leaks 158
Pressure and Temperature Corrections 159
Vacuum Distillation Notes 162
Class 3: Fractional Distillation 164
How This Works 164
Fractional Distillation Notes 167
Azeotropes 168
Class 4: Steam Distillation 168
External Steam Distillation 168
Internal Steam Distillation 170
Steam Distillation Notes 171
Simulated Bulb-to-Bulb Distillation: Fakelrohr 172
Exercises 173
Chapter 20 Microscale Distillation 175
Like the Big Guy 175
Class 1: Simple Distillation 175
Class 2: Vacuum Distillation 175
Class 3: Fractional Distillation 176
Class 4: Steam Distillation 176
Microscale Distillation II: The Hickman Still 176
The Hickman Still Setup 176
Hickman Still Heating 177
Recovering Your Product 178
A Port in a Storm 178
Chapter 21 The Rotary Evaporator 179
Exercises 182
Chapter 22 Reflux and Addition 183
Standard Reflux 183
A Dry Reflux 185
Addition and Reflux 186
Funnel Fun 186
How to Set Up 188
Exercise 189
Chapter 23 Reflux: Microscale 190
Addition and Reflux: Microscale 190
Chapter 24 Sublimation 192
Chapter 25 Microscale Boiling Point 195
Microscale Boiling Point 195
Ultramicroscale Boiling Point 197
Chapter 26 Chromatography: Some Generalities 199
Adsorbents 199
Separation or Development 200
The Eluatropic Series 200
Chapter 27 Thin-Layer Chromatography: TLC 202
We Don’t Make Our Own TLC Plates Any More, But… 202
Pre-prepared TLC Plates 203
The Plate Spotter 203
Spotting the Plates 204
Developing a Plate 205
Visualization 206
Interpretation 207
Multiple Spotting 209
Cospotting 210
Other TLC Problems 210
Preparative TLC 212
Exercises 212
Chapter 28 Wet-Column Chromatography 214
Preparing the Column 214
Compounds on the Column 216
Visualization and Collection 217
Wet-Column Chromatography: Microscale 218
Flash Chromatography 219
Microscale Flash Chromatography 220
Exercises 221
Chapter 29 Refractometry 222
The Abbé Refractometer 223
Before Using the Abbé Refractometer: A Little Practice 224
Using the Abbé Refractometer 225
Refractometry Hints 226
Chapter 30 Gas Chromatography 227
The Mobile Phase: Gas 227
GC Sample Preparation 228
GC Sample Introduction 228
Sample in the Column 230
Sample at the Detector 231
Electronic Interlude 232
Sample on the Computer 233
Parameters, Parameters 234
Gas Flow Rate 234
Temperature 234
Exercises 235
Chapter 31 HP Liquid Chromatography 236
The Mobile Phase: Liquid 237
A Bubble Trap 238
The Pump and Pulse Dampener Module 239
HPLC Sample Preparation 239
HPLC Sample Introduction 241
Sample in the Column 242
Sample at the Detector 242
Sample on the Computer 243
Parameters, Parameters 243
Eluent Flow Rate 244
Temperature 244
Eluent Composition 244
Exercises 244
Chapter 32 Infrared Spectroscopy (and a bit of uv-vis, too ) 245
Molecules As Balls On Springs 245
Ah, Quantum Mechanics 247
The Dissonant Oscillator 247
But Wait! There’s More 248
More Complicated Molecules 248
Correlation Tables to the Rescue 250
Troughs and Reciprocal Centimeters 254
Some Functional Group Analysis 254
A Systematic Interpretation 256
Infrared Sample Preparation 258
Liquid Samples 258
Solid Samples 259
Running the Spectrum 262
Interpreting IR Spectra—Finishing Touches 263
The Fourier Transform Infrared (FTIR) 264
The Optical System 264
A Reflectance Attachment: Something to Think About 268
And UV-VIS Too! 268
Electrons Get to Jump 268
Instrument Configuration 269
Source 270
Sample (and Reference) Cells 270
Solvents 270
Exercises 271
Chapter 32 On The Dual -Beam Infra-Red Instrument (ONLINE)1
The Perkin-Elmer 710B IR 2
Using the Perkin-Elmer 710B 4
The 100% Control: An Important Aside 5
Calibration of the Spectrum 6
IR Spectra: The Finishing Touches 7
Chapter 33 Nuclear Magnetic Resonance 272
Nuclei Have Spin, Too 272
The Magnetic Catch 273
Everybody Line Up, Flip, and Relax 273
A More Sensitive Census 274
The Chemical Shift 274
T For One and Two 275
Be It Better Resolved... 275
Incredibly Basic Ft-Nmr 276
Nmr Sample Preparation 276
Some Nmr Terms and Interpretations 280
The Chemical Shift and Tms Zero 280
Integration and Labeling 282
Threaded Interpretations: Spectrum #1 (t-butyl alcohol) 283
Threaded Interpretations: Spectrum #2 (Toluene) and Spectrum #3 (p-Dichlorobenzene) 283
Threaded Interpretations: Spectrum #4 (Ethylbenzene) and Spectrum #5 (A Double Resonance Experiment) 285
Use a Correlation Chart 288
Exercises 290
Chapter 34 Theory of Distillation (Online) 1
Class 1: Simple Distillation 1
Clausius and Clapeyron 3
Class 3: Fractional Distillation 5
A Hint from Dalton 5
Dalton and Raoult 5
A Little Algebra 6
Clausius and Clapeyron Meet Dalton and Raoult 7
Dalton Again 8
What Does It All Mean? 10
Reality Intrudes I: Changing Composition 12
Reality Intrudes II: Nonequilibrium Conditions 12
Reality Intrudes III: Azeotropes 13
Other Deviations 16
Class 4: Steam Distillation 16
Index 291
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