The Organic Chemistry Lab Survival Guide

by Zubrick, James W.

• ISBN13: 9780471387329
• ISBN10: 0471387320
• Format: Paperback
• Copyright: 2000-08-01
• Publisher: John Wiley & Sons Inc

Summary

A paperback guide to the basic techniques of the organic chemistry lab. Zubrick includes practical lab advice presented with clarity and humor. The book describes the instruments and techniques used in organic chemistry lab. Diagrams show the reader how to make measurements, set up labs and perform meaningful experiments.

Table of Contents

Safety First, Last, and Always	1	(8)
Accidents Will Not Happen	4	(1)
Disposing of Waste	4	(4)
Mixed Waste	6	(2)
Keeping a Notebook	8	(11)
A Technique Experiment	9	(3)
Notebook Notes	10	(2)
A Synthesis Experiment	12	(6)
Notebook Notes	14	(4)
The Acid Test	18	(1)
Interpreting a Handbook	19	(13)
CRC Handbook	19	(4)
Entry: 1-Bromobutane	19	(2)
Entry: Benzoic Acid	21	(2)
Lange's	23	(2)
Entry: 1-Bromobutane	23	(1)
Entry: Benzoic Acid	24	(1)
Merck Index	25	(3)
Entry: 1-Bromobutane	25	(3)
Entry: Benzoic Acid	28	(1)
The Aldrich Catalog	28	(3)
Entry: 1-Bromobutane	29	(1)
Entry: Benzoic Acid	30	(1)
Not Clear-Clear?	31	(1)
Info on the Internet	31	(1)
Jointware	32	(12)
Stoppers with Only One Number	32	(1)
Another Episode of Love of Laboratory	33	(2)
Hall of Blunders and Things Not Quite Right	35	(4)
Round-Bottom Flasks	35	(1)
Columns and Condensers	36	(1)
The Adapter with Lots of Names	36	(2)
Forgetting the Glass	38	(1)
Inserting Adapter Upside Down	39	(1)
Inserting Adapter Upside Down sans Glass	39	(1)
Greasing the Joints	39	(2)
To Grease or Not to Grease	39	(1)
Preparation of the Joints	40	(1)
Into the Grease Pit	40	(1)
Storing Stuff and Sticking Stoppers	41	(1)
Corking a Vessel	41	(2)
The Cork Press	43	(1)
The O-Ring & Cap Branch Out	43	(1)
Microscale Jointware	44	(11)
Microscale: A Few Words	44	(1)
Uh-Oh Rings	45	(1)
The O-Ring Cap Seal	45	(2)
Sizing Up the Situation	46	(1)
Why I Don't Really Know How Vacuum Tight These Seals Are	47	(1)
The Comical Vial (That's Conical!)	47	(4)
The Conical Vial as Vial	48	(1)
Packaging Oops	49	(1)
Tare to the Analytical Balance	49	(1)
The Electronic Analytical Balance	49	(1)
Heating These Vials	50	(1)
The Microscale Drying Tube	51	(1)
Gas Collection Apparatus	51	(4)
Generating the Gas	52	(2)
Isolating the Product	54	(1)
Other Interesting Equipment	55	(2)
Pipet Tips	57	(6)
Pre-preparing Pasteur Pipets	57	(3)
Calibration	57	(1)
Operation	57	(1)
Amelioration	58	(2)
Pipet Cutting	60	(1)
Pipet Filtering-Liquids	60	(1)
Pipet Filtering-Solids	61	(2)
Syringes, Needles, and Septa	63	(3)
The Rubber Septum	65	(1)
Clean and Dry	66	(2)
Drying Your Glassware When You Don't Need To	66	(1)
Drying Your Glassware When You Need To	67	(1)
Drying Agents	68	(3)
Typical Drying Agents	68	(1)
Using a Drying Agent	69	(1)
Following Directions and Losing Product Anyway	69	(1)
Drying Agents: Microscale	70	(1)
On Products	71	(2)
Solid Product Problems	71	(1)
Liquid Product Problems	71	(1)
The Sample Vial	72	(1)
Hold It! Don't Touch That Vial	72	(1)
The Melting Point Experiment	73	(16)
Sample Preparation	74	(2)
Loading the Melting Point Tube	74	(1)
Closing Off Melting Point Tubes	75	(1)
Melting Point Hints	76	(1)
The Mel-Temp Apparatus	76	(1)
Operation of the Mel-Temp Apparatus	76	(3)
The Fisher-Johns Apparatus	79	(1)
Operation of the Fisher-Johns Apparatus	79	(1)
The Thomas-Hoover Apparatus	80	(2)
Operation of the Thomas-Hoover Apparatus	82	(3)
Using the Thiele Tube	85	(4)
Cleaning the Tube	85	(1)
Getting the Sample Ready	85	(2)
Dunking the Melting Point Tube	87	(1)
Heating the Sample	87	(2)
Recrystallization	89	(15)
Finding a Good Solvent	90	(1)
General Guidelines for a Recrystallization	90	(1)
Gravity Filtration	91	(3)
The Buchner Funnel and Filter Flask	94	(2)
Just a Note	96	(1)
The Hirsch Funnel and Friends	96	(1)
Activated Charcoal	97	(1)
The Water Aspirator: A Vacuum Source	97	(2)
The Water Trap	99	(1)
Working with a Mixed-Solvent System---The Good Part	100	(1)
The Ethanol-Water System	100	(1)
A Mixed-Solvent System---The Bad Part	101	(1)
Salting Out	101	(1)
World Famous Fan-Folded Fluted Paper	102	(2)
Recrystallization: Microscale	104	(6)
Isolating the Crystals	105	(1)
Craig Tube Filtration	105	(3)
Centrifuging the Craig Tube	108	(2)
Getting the Crystals Out	109	(1)
Extraction and Washing	110	(13)
Never-Ever Land	111	(1)
Starting an Extraction	111	(1)
Dutch Uncle Advice	112	(1)
The Separatory Funnel	113	(3)
The Stopper	113	(1)
The Glass Stopcock	114	(1)
The Teflon Stopcock	115	(1)
The Stem	116	(1)
Washing and Extracting Various Things	116	(1)
How to Extract and Wash What	117	(6)
The Road to Recovery---Back-Extraction	118	(1)
A Sample Extraction	118	(2)
Performing an Extraction or Washing	120	(2)
Extraction Hints	122	(1)
Extraction and Washing: Microscale	123	(3)
Mixing	123	(1)
Separation: Removing the Bottom Layer	123	(1)
Separation: Removing the Top Layer	124	(2)
And Now---Boiling Stones	126	(1)
Sources of Heat	127	(8)
The Steam Bath	127	(1)
The Bunsen Burner	128	(2)
Burner Hints	129	(1)
The Heating Mantle	130	(2)
Proportional Heaters and Stepless Controllers	132	(3)
Clamps and Clamping	135	(9)
Clamping a Distillation Setup	137	(4)
Clipping a Distillation Setup	141	(3)
Distillation	144	(23)
Distillation Notes	145	(3)
Simple Distillation	145	(1)
Sources of Heat	146	(1)
The Three-Way Adapter	146	(1)
The Distilling Flask	146	(1)
The Thermometer Adapter	147	(1)
The Ubiquitous Clamp	147	(1)
The Thermometer	147	(1)
The Condenser	147	(1)
The Vacuum Adapter	148	(1)
The Receiving Flask	148	(1)
The Ice Bath	148	(1)
The Distillation Example	148	(1)
The Distillation Mistake	149	(13)
Vacuum Distillation	150	(1)
Pressure Measurement	150	(2)
Manometer Hints	152	(1)
Leaks	152	(1)
Pressure and Temperature Corrections	153	(2)
Vacuum Distillation Notes	155	(3)
Fractional Distillation	158	(1)
How This Works	158	(3)
Fractional Distillation Notes	161	(1)
Azeotropes	162	(2)
Steam Distillation	162	(1)
External Steam Distillation	162	(1)
Internal Steam Distillation	163	(1)
Steam Distillation Notes	164	(3)
Microscale Distillation	167	(4)
Like the Big Guy	167	(1)
Simple Distillation	167	(1)
Vacuum Distillation	167	(1)
Fractional Distillation	168	(1)
Steam Distillation	168	(1)
Microscale Distillation II: The Hickman Still	168	(3)
The Hickman Still Setup	168	(1)
Hickman Still Heating	169	(1)
Recovering Your Product	170	(1)
Reflux & Addition	171	(7)
Standard Reflux	171	(1)
A Dry Reflux	172	(2)
Addition and Reflux	174	(4)
Funnel Fun	174	(1)
How to Set Up	175	(3)
Reflux: Microscale	178	(2)
Addition and Reflux: Microscale	178	(2)
Sublimation	180	(2)
Microscale Boiling Point	182	(3)
Microscale BP	182	(1)
Ultramicroscale BP	183	(2)
Chromatography: Some Generalities	185	(3)
Adsorbents	185	(1)
Separation or Development	185	(1)
The Eluatropic Series	186	(2)
Thin-Layer Chromatography: TLC	188	(11)
Preparation of TLC Plates	188	(2)
Pre-prepared TLC Plates	189	(1)
The Plate Spotter	190	(1)
Spotting the Plates	190	(1)
Developing a Plate	191	(2)
Visualization	193	(1)
Interpretation	193	(2)
Multiple Spotting	195	(1)
Cospotting	196	(1)
Other TLC Problems	196	(2)
Preparative TLC	198	(1)
Wet-Column Chromatography	199	(7)
Preparing the Column	199	(2)
Compounds on the Column	201	(1)
Visualization and Collection	202	(1)
Wet-Column Chromatography: Microscale	203	(1)
Flash Chromatography	204	(1)
Microscale Flash Chromatography	205	(1)
Refractometry	206	(5)
The Abbe Refractometer	207	(1)
Using the Abbe Refractometer	208	(1)
Refractometry Hints	209	(2)
Instrumentation in the Lab	211	(2)
Gas Chromatography	213	(9)
The Mobile Phase: Gas	213	(1)
GC Sample Preparation	213	(1)
GC Sample Introduction	214	(2)
Sample in the Column	216	(1)
Sample at the Detector	216	(2)
Electronic Interlude	218	(1)
Sample on the Chart Recorder	219	(1)
Sample on the Computer Recorder	220	(1)
Parameters, Parameters	220	(2)
Gas Flow Rate	220	(1)
Temperature	220	(2)
HP Liquid Chromatography	222	(9)
The Mobile Phase: Liquid	222	(4)
A Bubble Trap	224	(1)
The Pump	224	(1)
The Pulse Dampener	224	(2)
HPLC Sample Preparation	226	(1)
HPLC Sample Introduction	227	(1)
Sample in the Column	228	(1)
Sample at the Detector	228	(1)
Sample on the Chart Recorder	229	(1)
Sample on the Computer Recorder	230	(1)
Parameters, Parameters	230	(1)
Eluent Flow Rate	230	(1)
Temperature	230	(1)
Eluent Composition	230	(1)
Infrared Spectroscopy	231	(23)
Infrared Sample Preparation	235	(5)
Liquid Samples	235	(1)
Solid Samples	236	(1)
The Nujol Mull	236	(2)
Solid KBr Methods	238	(1)
Preparing the Solid Solution	238	(1)
Pressing a KBr Disk---The Minipress	238	(1)
Pressing a KBr Disk---The Hydraulic Press	239	(1)
Running the Spectrum	240	(2)
The Perkin-Elmer 710B IR	242	(2)
Using the Perkin-Elmer 710B	244	(2)
The 100% Control: An Important Aside	244	(2)
Calibration of the Spectrum	246	(2)
IR Spectra: The Finishing Touches	248	(1)
Interpreting IRs	248	(1)
The Fourier Transform Infrared (FTIR)	249	(5)
The Optical System	249	(5)
Nuclear Magnetic Resonance	254	(10)
Liquid Sample Preparation	254	(2)
Solid Samples	256	(1)
Protonless Solvents	256	(1)
Deuterated Solvents	257	(1)
FT-NMR Sample Preparation	257	(1)
Some NMR Interpretation	258	(6)
The Zero Point	258	(1)
The Chemical Shift	258	(3)
Some Anisotropy	261	(1)
Spin-Spin Splitting	261	(2)
Integration	263	(1)
A Final Note	263	(1)
Theory of Distillation	264	(17)
Simple Distillation	264	(1)
Clausius and Clapeyron	265	(2)
Fractional Distillation	267	(1)
A Hint from Dalton	267	(1)
Dalton and Raoult	268	(1)
A Little Algebra	268	(1)
Clausius and Clapeyron Meet Dalton and Raoult	269	(1)
Dalton Again	270	(1)
What Does It All Mean?	271	(3)
Reality Intrudes I: Changing Composition	274	(1)
Reality Intrudes II: Nonequilibrium Conditions	275	(1)
Reality Intrudes III: Azeotropes	275	(3)
Minimum-Boiling Azeotropes	276	(1)
Maximum-Boiling Azeotropes	277	(1)
Azeotropes on Purpose	277	(1)
Other Deviations	278	(3)
Steam Distillation	279	(2)
Theory of Extraction	281	(3)
Index	284