The Organic Chem Lab Survival Manual: A Student's Guide to Techniques

by Zubrick, James W.

• ISBN13: 9780471129486
• ISBN10: 0471129488
• Edition: 4th
• Format: Paperback
• Copyright: 1997-01-01
• Publisher: John Wiley & Sons Inc

Summary

This book describes the instruments and techniques that are used in an organic lab. It contains vital directions for obtaining information on organic chemistry labs from the Internet.

Table of Contents

1. Safety First, Last, and Always	1	(10)
Accidents Will Not Happen	5	(1)
Disposing of Waste	6	(5)
Mixed Waste	8	(3)
2. Keeping a Notebook	11	(14)
A Technique Experiment	13	(1)
Notebook Notes	13	(1)
A Synthesis Experiment	13	(11)
Notebook Notes	17	(7)
The Acid Test	24	(1)
3. Interpreting a Handbook	25	(20)
CRC Handbook	26	(5)
Entry: 1-Bromobutane	26	(2)
Entry: Benzoic Acid	28	(1)
Nostalgia	29	(2)
Lange's	31	(3)
Entry: 1-Bromobutane	31	(1)
Entry: Benzoic Acid	31	(3)
Merck Index	34	(5)
Entry: 1-Bromobutane	35	(3)
Entry: Benzoic Acid	38	(1)
The Aldrich Catalog	39	(2)
Entry: 1-Bromobutane	39	(1)
Entry: Benzoic Acid	40	(1)
Not Clear--Clear?	41	(1)
Info on the Internet	41	(4)
How to Start	42	(1)
I'm Logged On--Now What?	42	(2)
So Talk to Me	44	(1)
4. Jointware	45	(14)
Stoppers with Only One Number	46	(1)
Another Episode of Love of Laboratory	47	(2)
Hall of Blunders and Things Not Quite Right	49	(4)
Round-Bottom Flasks	49	(1)
Columns and Condensers	50	(1)
The Adapter with Lots of Names	51	(2)
Forgetting the Glass	53	(1)
Inserting Adapter Upside Down	53	(1)
Inserting Adapter Upside Down sans Glass	53	(1)
Greasing the Joints	53	(2)
To Grease or Not to Grease	54	(1)
Preparation of the Joints	54	(1)
Into the Grease Pit	55	(1)
Storing Stuff and Sticking Stoppers	55	(3)
Corking a Vessel	58	(1)
The Cork Press	58	(1)
5. Microscale Jointware	59	(14)
Microscale: A Few Words	60	(1)
The O-Ring Cap Seal	61	(3)
Sizing Up the Situation	62	(1)
Why I Don't Really Know How Vacuum Tight These Seals Are	63	(1)
The Comical Vial (That's Conical!)	64	(4)
The Conical Vial as Vial	64	(1)
Packaging Oops	65	(1)
Tare to the Analytical Balance	65	(1)
The Electronic Analytical Balance	66	(1)
Heating These Vials	67	(1)
The Microscale Drying Tube	68	(1)
Gas Collection Apparatus	68	(5)
Generating the Gas	70	(2)
Isolating the Product	72	(1)
Some Present-day Gas-Collecting Ironies	72	(1)
6. Other Interesting Equipment	73	(4)
7. Pipet Tips	77	(8)
Pre-preparing Pasteur Pipets	78	(3)
Calibration	79	(1)
Operation	79	(1)
Amelioration	79	(2)
Pipet Cutting	81	(1)
Pipet Filtering--Liquids	82	(1)
Pipet Filtering--Solids	82	(3)
8. Syringes, Needles, and Septa	85	(4)
The Rubber Septum	87	(2)
9. Clean and Dry	89	(4)
Drying Your Glassware When You Don't Need To	90	(1)
Drying Your Glassware When You Need To	90	(3)
10. Drying Agents	93	(4)
Typical Drying Agents	94	(1)
Using a Drying Agent	95	(1)
Following Directions and Losing Product Anyway	95	(1)
Drying Agents: Microscale	96	(1)
11. On Products	97	(4)
Solid Product Problems	98	(1)
Liquid Product Problems	98	(1)
The Sample Vial	98	(1)
Hold It! Don't Touch That Vial	99	(2)
12. The Melting Point Experiment	101	(20)
Sample Preparation	102	(3)
Loading the Melting Point Tube	103	(1)
Closing Off Melting Point Tubes	104	(1)
Melting Point Hints	105	(1)
The Mel-Temp Apparatus	105	(2)
Operation of the Mel-Temp Apparatus	107	(1)
The Fisher-Johns Apparatus	108	(1)
Operation of the Fisher-Johns Apparatus	109	(1)
The Thomas-Hoover Apparatus	110	(2)
Operation of the Thomas--Hoover Apparatus	112	(3)
Using The Thiele Tube	115	(6)
Cleaning the Tube	117	(1)
Getting the Sample Ready	117	(1)
Dunking the Melting Point Tube	118	(1)
Heating the Sample	118	(3)
13. Recrystallization	121	(18)
Finding a Good Solvent	122	(1)
General Guidelines for a Recrystallization	123	(1)
Gravity Filtration	124	(3)
The Buchner Funnel and Filter Flask	127	(3)
Just a Note	129	(1)
Activated Charcoal	130	(1)
The Water Aspirator: A Vacuum Source	131	(1)
The Water Trap	132	(1)
Working with a Mixed-Solvent System--The Good Part	132	(2)
The Ethanol-Water System	133	(1)
A Mixed-Solvent System--The Bad Part	134	(1)
Salting Out	135	(1)
World Famous Fan-Folded Fluted Paper	136	(3)
14. Recrystallization: Microscale	139	(8)
Isolating the Crystals	141	(1)
Craig Tube Filtration	141	(3)
Centrifuging the Craig Tube	144	(3)
Getting the Crystals Out	147	(1)
15. Extraction and Washing	147	(18)
Never-Ever Land	149	(1)
Starting an Extraction	149	(2)
Dutch Uncle Advice	151	(1)
The Separatory Funnel	152	(3)
The Stopper	153	(1)
The Glass Stopcock	153	(1)
The Teflon Stopcock	154	(1)
The Stem	155	(1)
Washing and Extracting Various Things	155	(1)
How to Extract and Wash What	156	(9)
The Road to Recovery--Back-Extraction	157	(1)
A Sample Extraction	158	(2)
Performing an Extraction or Washing	160	(2)
Extraction Hints	162	(3)
16. Extraction and Washing: Microscale	165	(4)
Mixing	166	(1)
Separation: Removing the Bottom Layer	166	(1)
Separation: Removing the Top Layer	166	(3)
17. And Now--Boiling Stones	169	(2)
18. Sources of Heat	171	(10)
The Steam Bath	172	(1)
The Bunsen Burner	173	(3)
Burner Hints	174	(2)
The Heating Mantle	176	(1)
Proportional Heaters and Stepless Controllers	177	(4)
19. Clamps and Clamping	181	(12)
Clamping a Distillation Setup	184	(3)
Clipping a Distillation Setup	187	(6)
20. Distillation	193	(28)
Distillation Notes	195	(1)
Class 1: Simple Distillation	195	(4)
Sources of Heat	195	(1)
The Three-Way Adapter	195	(1)
The Distilling Flask	196	(2)
The Thermometer Adapter	198	(1)
The Ubiquitous Clamp	198	(1)
The Thermometer	198	(1)
The Condenser	198	(1)
The Vacuum Adapter	198	(1)
The Receiving Flask	199	(1)
The Ice Bath	199	(1)
The Distillation Example	199	(1)
The Distillation Mistake	200	(1)
Class 2: Vacuum Distillation	201	(10)
Pressure Measurement	201	(1)
Manometer Hints	202	(2)
Leaks	204	(1)
Pressure and Temperature Corrections	205	(3)
Vacuum Distillation Notes	208	(3)
Class 3: Fractional Distillation	211	(3)
How This Works	213	(1)
Fractional Distillation Notes	214	(1)
Azeotropes	214	(1)
Class 4: Steam Distillation	215	(6)
External Steam Distillation	216	(1)
Internal Steam Distillation	217	(2)
Steam Distillation Notes	219	(2)
21. Microscale Distillation	221	(6)
Like the Big Guy	222	(1)
Class 1: Simple Distillation	222	(1)
Class 2: Vacuum Distillation	222	(1)
Class 3: Fractional Distillation	223	(1)
Class 4: Steam Distillation	223	(1)
Microscale Distillation II: The Hickman Still	223	(4)
The Hickman Still Setup	223	(2)
The Hickman Still Heating	225	(1)
Recovering Your Product	225	(2)
22. Reflux & Addition	227	(10)
Standard Reflux	228	(1)
A Dry Reflux	229	(2)
Addition and Reflux	231	(6)
Funnel Fun	232	(1)
How to Set Up	233	(4)
23. Reflux: Microscale	237	(4)
Addition and Reflux: Microscale	238	(3)
24. Sublimation	241	(4)
25. Microscale Boiling Point	245	(6)
Microscale B.P.	246	(1)
Ultramicroscale B.P.	247	(4)
26. Chromatography: Some Generalities	251	(4)
Adsorbents	252	(1)
Separation or Development	252	(1)
The Eluatropic Series	253	(2)
27. Thin-Layer Chromatography: TLC	255	(14)
Preparation of TLC Plates	256	(1)
The Plate Spotter	257	(1)
Spotting the Plates	258	(1)
Developing a Plate	259	(2)
Visualization	261	(1)
Interpretation	262	(2)
Multiple Spotting	264	(1)
Pre-prepared TLC Plates	264	(1)
Cospotting	265	(1)
Other TLC Problems	266	(1)
Preparative TLC	267	(2)
28. Wet-Column Chromatography	269	(10)
Preparing the Column	270	(2)
Compounds on the Column	272	(1)
Visualization and Collection	273	(1)
Wet-Column Chromatography: Microscale	274	(2)
Flash Chromatography	276	(1)
Microscale Flash Chromatography	277	(2)
29. Refractometry	279	(6)
The Abbe Refractometer	280	(2)
Using the Abbe Refractometer	282	(1)
Refractometry Hints	283	(2)
30. Instrumentation in the Lab	285	(4)
31. Gas Chromatography	289	(12)
The Mobile Phase: Gas	290	(1)
GC Sample Preparation	290	(1)
GC Sample Introduction	291	(1)
Sample in the Column	292	(2)
Sample at the Detector	294	(2)
Electronic Interlude	296	(1)
Sample on the Chart Recorder	297	(1)
Parameters, Parameters	298	(3)
Gas Flow Rate	298	(1)
Temperature	299	(2)
32. HP Liquid Chromatography	301	(12)
The Mobile Phase: Liquid	302	(4)
A Bubble Trap	304	(1)
The Pump	305	(1)
The Pulse Dampener	305	(1)
HPLC Sample Preparation	306	(2)
HPLC Sample Introduction	308	(1)
Sample in the Column	309	(1)
Sample at the Detector	310	(1)
Sample on the Chart Recorder	311	(1)
Parameters, Parameters	311	(2)
Eluent Flow Rate	311	(1)
Temperature	312	(1)
Eluent Composition	312	(1)
33. Infrared Spectroscopy	313	(26)
Infrared Sample Preparation	318	(6)
Liquid Samples	318	(2)
Solid Samples	320	(1)
The Nujol Mull	320	(1)
Solid KBr Methods	320	(2)
Preparing the Solid Solution	322	(1)
Pressing a KBr Disk--The Minipress	322	(1)
Pressing a KBr Disk--The Hydraulic Press	323	(1)
Running the Spectrum	324	(2)
The Perkin-Elmer 710B IR	326	(2)
Using the Perkin-Elmer 710B	328	(2)
The 100% Control: An Important Aside	328	(2)
Calibration of the Spectrum	330	(2)
IR Spectra: The Finishing Touches	332	(1)
Interpreting IRs	333	(1)
The Fourier Transform Infrared (FTIR)	334	(5)
The Optical System	334	(5)
34. Nuclear Magnetic Resonance (NMR)	339	(12)
Liquid Sample Preparation	340	(2)
Solid Samples	342	(1)
Protonless Solvents	342	(1)
Deuterated Solvents	342	(1)
FT-NMR Sample Preparation	343	(1)
Some NMR Interpretation	344	(7)
The Zero Point	344	(1)
The Chemical Shift	344	(3)
Some Anisotropy	347	(1)
Spin-Spin Splitting	348	(2)
Integration	350	(1)
A Final Note	350	(1)
35. Theory of Distillation	351	(22)
Class 1: Simple Distillation	352	(4)
Clausius and Clapeyron	353	(3)
Class 3: Fractional Distillation	356	(14)
A Hint from Dalton	356	(1)
Dalton and Raoult	356	(1)
A Little Algebra	357	(2)
Clausius and Clapeyron Meet Dalton and Raoult	359	(1)
Dalton Again	360	(3)
What Does It All Mean?	363	(2)
Reality Intrudes I: Changing Composition	365	(1)
Reality Intrudes II: Nonequilibrium Conditions	365	(1)
Reality Intrudes III: Azeotropes	366	(1)
Minimum-Boiling Azeotropes	367	(1)
Maximum-Boiling Azeotropes	367	(1)
Azeotropes on Purpose	367	(3)
Other Deviations	370	(1)
Class 4: Steam Distillation	370	(3)
36. Theory of Extraction	373	(4)
Index	377