Organic Chemistry Laboratory Standard and Microscale Experiments

by Bell, Charles E.; Taber, Douglas; Clark, K.

• ISBN13: 9780030292729
• ISBN10: 0030292727
• Edition: 3rd
• Format: Hardcover
• Copyright: 2000-08-09
• Publisher: Brooks Cole

Summary

The new edition continues to offer a wide variety of organic lab experiments for both standard and microscale formats and features unusually strong coverage of spectroscopy.

Table of Contents

Preface	xiii
Introduction	1	(16)
Laboratory Safety	1	(3)
Disposal	4	(1)
Laboratory Equipment and Techniques	5	(7)
Reports and Records	12	(5)
Melting Points	17	(6)
Melting Point of a Pure Known Compound	20	(1)
Melting Points as a Thermometer Calibration	21	(1)
Melting Point of an Unknown Compound	21	(2)
Recrystallization	23	(10)
Recrystallization of Benzoic Acid (Microscale)	29	(1)
Crystallization of Impure Acetanilide (Macroscale)	29	(1)
Preparation of Acetanilide (Microscale)	30	(1)
Preparation of N-Acetylanthranilic Acid: A Triboluminescent Material (Macroscale)	31	(2)
Extraction	33	(14)
Determination of a Distribution Coefficient (Macroscale)	41	(1)
Separation of Acidic, Basic, and Neutral Compounds (Macroscale)	42	(2)
Separation of Acidic, Basic, and Neutral Compounds (Microscale)	44	(3)
Distillation	47	(12)
Distillation of a Pure Compound (Macroscale)	54	(1)
Simple Distillation of a Mixture (Macroscale)	54	(1)
Fractional Distillation (Macroscale)	54	(1)
Fractional Distillation (Microscale)	55	(1)
Boiling Points (Reflux Boiling Point Method)	55	(1)
Micro Boiling Point Determination (Thiele--Dennis Tube Method)	55	(2)
Micro Boiling Point Determination (Capillary Method)	57	(2)
Gas Chromatography	59	(8)
Examination of an Unknown Mixture	64	(1)
GC of Fractions from Fractional Distillation	65	(2)
Column Chromatography	67	(6)
Separation of Ferrocene and Acetylferrocene (Microscale)	69	(1)
Isolation of Caffeine	70	(3)
Thin Layer Chromatography	73	(8)
TLC of Nitroanilines	75	(1)
TLC of Analgesic Drugs	76	(5)
High Performance Liquid Chromatography (HPLC)	81	(4)
Caffeine in Beverages	82	(3)
Steam Distillation of Essential Oils	85	(8)
Isolation of the Essential Oils of Caraway, Clove, or Cumin (Macroscale)	88	(1)
Isolation of the Essential Oil of Caraway (Microscale)	88	(1)
Caraway Oil (Macro- and Microscale)	89	(1)
Clove Oil (Macroscale)	90	(1)
Cumin Oil (Macroscale)	91	(2)
Infrared Absorption Spectroscopy	93	(14)
Spectroscopic Structure Determination: A Lifelong Quest	107	(18)
H- Nuclear Magnetic Resonance	125	(18)
Proton Spectrum of Ethylbenzene	132	(1)
Proton Spectra of Alcohols	132	(1)
Carbon-13 Spectrum of Ethylbenzene	133	(1)
Acquire the Spectra of an Unknown Compound Supplied by Your Instructor, and Determine the Structure	133	(10)
Advanced Structure Determination	143	(28)
The Literature of Organic Chemistry	171	(12)
Properties of Hydrocarbons	183	(4)
Solubility	184	(1)
Relative Density	184	(1)
Flammability	184	(1)
Addition of Bromine	184	(1)
Reaction with Potassium Permanganate	184	(1)
Reaction with Sulfuric Acid	184	(3)
Nucleophilic Substitution of Alkyl Halides	187	(6)
Structural Effects on SN1 and SN2 Reactivity	188	(1)
Effects of Solvent on SN1 Reactivity	189	(1)
Effect of Temperature on Reaction Rates	190	(1)
Reaction of Ethyl Bromide with Hydroxide Ion, an SN2 Reaction	191	(2)
Properties of Alcohols	193	(4)
Reaction with Sodium (Demonstation)	193	(1)
Solubility in Water	194	(1)
Lucas Test	194	(1)
Oxidation Using Chromic Acid	195	(1)
Ester Formation	195	(2)
The Grignard Reaction	197	(8)
Triphenylmethanol and Benzoic Acid (Macro- and Microscale)	198	(2)
Preparation of Triphenylmethanol (Macro- and Microscale)	200	(2)
Preparation of Benzoic Acid (Macro- and Microscale)	202	(1)
Preparation of Malachite Green	203	(2)
Dehydration of Alcohols	205	(6)
Preparation of Cyclohexene (Macroscale)	206	(1)
Dehydration of 2-Methylcyclohexanol (Macroscale)	207	(1)
Dehydration of 2-Methylcyclohexanol (Microscale)	208	(3)
Oxidation and Reduction	211	(8)
Preparation of Cyclohexanone (Macroscale)	213	(1)
Preparation of Adipic Acid (Microscale)	214	(1)
Oxidation of para-Nitrobenzyl alcohol (Microscale)	214	(1)
Haloform Reaction (Microscale)	215	(1)
Reduction of Benzophenone (Microscale)	216	(1)
Reduction of para-Nitrobenzyaldehyde (Microscale)	216	(3)
Aldehydes and Ketones	219	(6)
Reactions with Nitrogen Compounds	220	(1)
Oxidation Reactions	221	(1)
Iodoform Test	222	(1)
Infrared Spectra	222	(1)
Crossed Aldol Condensation (Microscale)	222	(3)
Determination of pKa: Effects of Substituents on Acidity	225	(4)
Determination of the pKa of Unknown Substituted Benzoic Acid (Microscale)	226	(3)
Carboxylic Acid Mini-Unknown	229	(4)
Esterification and Saponification: Effects of Substituents on Reactivity	233	(4)
Preparation of Methyl Benzoates (Microscale)	233	(1)
Rate Measurements	234	(1)
Calculation of the Rate Constant for Hydrolysis	235	(2)
Friedel-Crafts Alkylation and Acylation	237	(6)
Preparation of BHT (Macroscale)	238	(2)
Preparation of p-di-t-Butylbenzene (Microscale)	240	(1)
Friedel-Crafts Synthesis of an Unsymmetrical Diaryl Ketone	241	(2)
Aromatic Nitration	243	(6)
Preparation and Separation of o- and p-Nitroaniline (Macroscale)	244	(2)
Nitration of Toluene and Analysis of Products (Microscale)	246	(3)
Aromatic Nucleophilic Substitution	249	(6)
Preparation of 2,4-Dinitrophenol (Microscale)	251	(1)
Reaction of 2,4-Dinitrohalobenzenes with Ammonia and Hydrazine (Microscale)	251	(4)
Properties of Amines	255	(4)
Solubility in Water	255	(1)
Basicity	256	(1)
Hinsberg Test	256	(1)
Reactions of Diazonium Salts (Microscale)	256	(3)
Chemiluminescence	259	(6)
Bis-(2,4-Dinitrophenyl) Oxalate (Microscale)	261	(1)
Chemiluminescence (Microscale)	262	(3)
Photodimerization of Benzophenone	265	(4)
Photochemical Preparation of Benzopinacol (Microscale)	266	(1)
Preparation of Benzopinacolone (Microscale)	266	(3)
The Diels-Alder Reaction	269	(6)
Endo-Norbornene-5,6-cis-Dicarboxylic Anhydride (Macroscale)	271	(1)
Endo-Norbornene-5,6-cis-Dicarboxylic Anhydride (Microscale)	271	(4)
Phase Transfer Catalysis	275	(4)
Preparation of Nerolin (Macroscale)	276	(3)
Derivatives of Carboxylic Acids: Synthesis of a Plant Hormone	279	(4)
Acid Chloride Method (Microscale)	281	(1)
Nitrile Method (Microscale)	281	(2)
Synthesis of Coumarin	283	(6)
Ethyl Coumarin-3-carboxylate (Macroscale)	284	(1)
Coumarin-3-carboxylic Acid	285	(1)
Coumarin	285	(4)
Benzyne	289	(4)
1,4-Dihydronaphthalene- 1,4-endoxide (Microscale)	290	(1)
1-Naphthol (Microscale)	290	(3)
Heterocyclic Syntheses: Pyrimidines, Pyridones, Isoxazoles, Quinolines, and Indoles	293	(8)
Reactions of Acetylacetone with Nucleophiles	294	(2)
Reaction with Cyanoacetamide	295	(1)
Reaction with Guanidine	295	(1)
Reaction with Hydrazine	295	(1)
Reaction with Hydroxylamine	295	(1)
4-(p-Toluidino)-3-penten-2-one (Microscale)	296	(1)
2,4,6-Trimethylquinoline (Microscale)	296	(1)
3-Acetyl-2-methyl-4-phenylpyrrole (Macroscale)	297	(1)
3-Acetyl-2,4,6-trimethylpyridine (Macroscale)	298	(1)
3,5-Diacetyl-2,4,6-trimethyl-1,4-dihydropyridine (Macroscale)	298	(3)
Heterocyclic Synthesis: Phenytoin	301	(4)
Preparation of Phenytoin (Microscale)	302	(3)
Synthesis of Sulfanilamide	305	(4)
Synthesis of para-Acetamidobenzenesulfonyl Chloride	307	(1)
Amination of p-Acetamidobenzenesulfonyl Chloride	307	(1)
Sulfanilamide	307	(2)
Resolution of α-Phenylethylamine	309	(6)
Chemistry of Sugars	315	(8)
Thin-Layer Chromatography of Sugars	318	(1)
Characterization Reactions	319	(1)
Isomerization of Glucose	319	(1)
N-p-Tolyl-D-glucosylamine and N-p-Tolyl-1-amino-1-deoxy-D-fructose	320	(3)
Acid-Catalyzed and Enzyme-Catalyzed Hydrolysis of Polysaccharides	323	(4)
Enzymatic Hydrolysis of Starch	324	(1)
Acid Hydrolysis of Starch	324	(3)
Analysis of Fats and Oils	327	(4)
Transesterification of Triglycerides (Microscale)	329	(1)
GC Analysis of Methyl Esters	329	(1)
Isolation of Trimyristin (Microscale)	329	(1)
Hydrolysis of Trimyristin	329	(2)
Synthetic Organic Polymers	331	(8)
Polystyrene (Microscale)	332	(2)
Nylon (Microscale)	334	(1)
Polyurethanes (Microscale)	335	(4)
Dyes and Dyeing	339	(8)
Dyeing the Fiber (Microscale)	343	(1)
Comparison of Mono- and Dis-Azo Dyes in Neutral and Acid Solution (Microscale)	344	(1)
Disperse and Cross-Dyeing (Microscale)	344	(1)
Cationic Dyes (Microscale)	344	(3)
Qualitative Organic Analysis	347	(34)
Physical Properties	348	(3)
Solubility Classification	351	(2)
Analytical Data	353	(1)
Detection of Other Elements	354	(2)
Equivalent Weights	356	(1)
Miscellaneous Chemical Tests	357	(1)
Derivatives	358	(23)
Appendix A Selected Atomic Weights	381	(1)
Appendix B Common Acids and Bases	382	(1)
Appendix C Common Organic Liquids	383	(1)
Appendix D Representative Calculations	384	(3)
Index	387