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The Organic Chem Lab Survival Manual

by: Zubrick, James W.

The Organic Chem Lab Survival Manual

by: Zubrick, James W.

ISBN 13:
9781118875780
ISBN 10:
1118875788
Edition: 10th
Format: Paperback
Copyright: 01/19/2016
Publisher: Wiley
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The Organic Chem Lab Survival Manual > ISBN13: 9781118875780

Summary

Written for the laboratory that accompanies the sophomore/junior level courses in Organic Chemistry, Zubrick provides students with a valuable guide to the basic techniques of the Organic Chemistry lab. The book will help students understand and practice good lab safety. It will also help students become familiar with basic instrumentation, techniques and apparatus and help them master the latest techniques such as interpretation of infrared spectroscopy. The guide is mostly macroscale in its orientation.

Author Biography

James W. Zubrick is the author of The Organic Chem Lab Survival Manual: A Student's Guide to Techniques, 10th Edition, published by Wiley.

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

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