Organic Chemistry Laboratory Standard and Microscale Experiments,9780030292729

Organic Chemistry Laboratory Standard and Microscale Experiments

by ; ;
Edition: 3rd
ISBN13: 9780030292729
ISBN10: 0030292727
Format: Hardcover
Pub. Date: 2000-08-09
Publisher(s): Brooks Cole
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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

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