Experimental Organic Chemistry A Miniscale and Microscale Approach

by Gilbert, John C.; Martin, Stephen F.

• ISBN13: 9780495013341
• ISBN10: 049501334X
• Edition: 4th
• Format: Hardcover
• Copyright: 2005-11-11
• Publisher: Brooks Cole

Summary

This proven and well-tested laboratory manual for organic chemistry students contains procedures for both miniscale (also known as small scale) and microscale users. This lab manual gives students all the necessary background to enter the laboratory with the knowledge to perform the experiments with confidence. For the microscale labs, experiments were chosen to provide tangible quantities of material, which can then be analyzed. Chapters 1-2 introduce students to the equipment, record keeping, and safety of the laboratory. Chapters 3-6, and 8 are designed to introduce students to laboratory techniques needed to perform all experiments. In Chapters 7 and 9 through 20, students are required to use the techniques to synthesize compounds and analyze their properties. In Chapter 21, students are introduced to multi-step syntheses of organic compounds, a practice well known in chemical industry. In Chapter 23, students are asked to solve structures of unknown compounds. The new chapter 24 introduces a meaningful experiment into the textbook that reflects the increasing emphasis on bioorganic chemistry in the sophomore-level organic lecture course. This experiment not only gives students the opportunity to accomplish a mechanistically interesting and synthetically important coupling of two a-amino acids to produce a dipeptide but also provides valuable experience regarding the role of protecting groups in effecting synthetic transformations with multiple functionalized molecules.

Table of Contents

Introduction, Record Keeping, and Laboratory Safety	1	(26)
Introduction	1	(1)
Preparing for the Laboratory	2	(1)
Working in the Laboratory	3	(1)
The Laboratory Notebook	4	(1)
General Protocol for the Laboratory Notebook	4	(1)
Types of Organic Experiments and Notebook Formats	5	(9)
Sample Calculations for Notebook Records	14	(2)
Safe Laboratory Practice: Overview	16	(1)
Safety: General Discussion	17	(2)
Safety: Material Safety Data Sheets	19	(2)
Safety: Disposal of Chemicals	21	(6)
Historical Highlights: The Importance of Record Keeping	24	(3)
Techniques and Apparatus	27	(66)
Glassware: Precautions and Cleaning	27	(1)
Standard-Taper Glassware for Miniscale Procedures	28	(1)
Standard-Taper Glassware for Microscale Procedures	29	(2)
Assembling Apparatus	31	(1)
Measuring and Transferring Liquids	32	(5)
Weighing Methods	37	(1)
Melting-Point Methods and Apparatus	38	(3)
Boiling-Point Methods and Apparatus	41	(2)
Heating Methods	43	(8)
Cooling Techniques	51	(1)
Stirring Methods	52	(2)
Centrifugation	54	(1)
Simple Distillation	55	(3)
Fractional Distillation	58	(2)
Vacuum Distillation	60	(4)
Steam Distillation	64	(2)
Filtration Apparatus and Techniques	66	(6)
Decolorizing Carbon	72	(1)
Decanting Solutions	73	(1)
Sublimation	73	(2)
Extraction	75	(6)
Heating Under Reflux	81	(2)
Gas Traps	83	(2)
Drying Agents	85	(2)
Drying Organic Solutions	87	(1)
Drying Solids	87	(1)
Drying Tubes	88	(1)
Drying Apparatus	88	(1)
Evaporating Solvents	89	(4)
Solids: Recrystallization and Melting Points	93	(30)
Introduction	93	(1)
Recrystallization	94	(19)
Recrystallization	101	(1)
Solvent Selection	101	(2)
Recrystallizing Impure Solids	103	(1)
Miniscale Procedures	103	(3)
Microscale Procedures	106	(7)
Physical Constants: Melting Points	113	(10)
Melting Points	117	(1)
Calibration of Thermometer	117	(1)
Determining Capillary-Tube Melting Points	118	(1)
Discovery Experiment	119	(1)
Melting-Point Depression	119	(4)
Liquids: Distillation and Boiling Points	123	(26)
Introduction	123	(1)
Boiling Points of Pure Liquids	123	(4)
Boiling Points of Pure Liquids	125	(1)
Miniscale Procedure	125	(1)
Microscale Procedure	125	(2)
Simple Distillation	127	(4)
Simple Distillation	129	(1)
Miniscale Procedure	129	(1)
Optional Procedure	130	(1)
Microscale Procedure	130	(1)
Fractional Distillation	131	(10)
Fractional Distillation of a Binary Mixture	137	(1)
Miniscale Procedure	137	(1)
Discovery Experiment	138	(1)
Comparative Fractional Distillations	138	(1)
Fractionation of Alternative Binary Mixtures	138	(3)
Steam Distillation	141	(2)
Steam Distillation: Isolation of Citral from Lemon Grass Oil	143	(6)
Steam Distillation of Citral from Lemon Grass Oil	144	(1)
Miniscale Procedure	145	(2)
Historical Highlights: Reducing Automobile Emissions	147	(2)
Extraction	149	(26)
Introduction	149	(1)
Theory of Extraction	150	(2)
Base and Acid Extractions	152	(15)
Base and Acid Extractions	157	(1)
Miniscale Procedures	157	(3)
Microscale Procedures	160	(3)
Discovery Experiment	163	(1)
Separation of Unknown Mixture by Extraction	163	(1)
Isolation of Ibuprofen	163	(4)
Extraction of a Natural Product: Trimyristin	167	(8)
Isolation of Trimyristin from Nutmeg	168	(1)
Miniscale Procedure	168	(1)
Microscale Procedure	169	(2)
Historical Highlights: Natural Products	171	(4)
Chromatography	175	(34)
Introduction	175	(1)
Thin-Layer Chromatography	176	(8)
Separation of Spinach Pigments by TLC	180	(2)
Discovery Experiment	182	(1)
Effect of Solvent Polarity on Efficiency of Separation	182	(1)
Analysis of Plant Pigments from Various Sources	182	(1)
Separation of Syn- and Anti-Azobenzenes by TLC	182	(1)
Discovery Experiment	183	(1)
Analysis of Analgesics by TLC	183	(1)
Column Chromatography	184	(8)
Column Chromatography	188	(2)
Discovery Experiment	190	(1)
Column Chromatographic Separation of Benzyl Alcohol and Methyl Benzoate	190	(2)
Gas-Liquid Chromatography	192	(17)
Qualitative and Quantitative Analyses of a Mixture of Compounds by GLC	202	(1)
Discovery Experiment	203	(1)
Analysis of Factors Affecting Retention Times	203	(1)
Effect of Stationary Phase on Separation of a Mixture	203	(1)
Determining GLC Response Factors	203	(1)
Discovery Experiment	204	(1)
Molar Response Factors of Isomers	204	(1)
Molar Response Factors of Nonisomeric Compounds	204	(2)
Historical Highlights: Who's Taking What? Analysis of Biological Fluids for Illegal Substances	206	(3)
Stereoisomers	209	(24)
Introduction	209	(3)
Separation of Diastereomeric 1,2-Cyclohexanediols	212	(3)
Separation of Diastereomeric 1,2-Cyclohexanediols	213	(2)
Isomerization of Dimethyl Maleate to Dimethyl Fumarate	215	(4)
Isomerization of Dimethyl Maleate to Dimethyl Fumarate	216	(1)
Miniscale Procedure	217	(1)
Microscale Procedure	217	(1)
Discovery Experiment	218	(1)
Assessing Purities of Dimethyl Maleate and Fumarate	218	(1)
Properties of the Enantiomers of Carvone	219	(4)
Properties of the Enantiomeric Carvones	221	(2)
Polarimetry	223	(2)
Resolution of Racemic 1-Phenylethanamine	225	(8)
Resolution of Racemic 1-Phenylethanamine	226	(1)
Miniscale Procedure	227	(2)
Historical Highlights: Discovery of Stereoisomers	229	(4)
Spectral Methods	233	(76)
Introduction	233	(3)
Infrared (IR) Spectroscopy	236	(21)
Nuclear Magnetic Resonance (NMR) Spectroscopy	257	(36)
Ultraviolet and Visible Spectroscopy	293	(7)
Mass Spectrometry	300	(9)
Historical Highlights: Medical Diagnostics via Nuclear Magnetic Resonance Spectroscopy	307	(2)
Alkanes	309	(24)
Introduction	309	(1)
Chlorination Using Sulfuryl Chloride	310	(10)
Free-Radical Chain Chlorination of 1-Chlorobutane	313	(1)
Miniscale Procedure	313	(1)
Microscale Procedure	314	(1)
Discovery Experiment	315	(1)
Chlorination of Heptane	315	(5)
Bromination: Selectivity of Hydrogen Atom Abstraction	320	(13)
Relative Rates of Free-Radical Chain Bromination	322	(7)
Historical Highlights: Keeping It Cool	329	(4)
Alkenes	333	(62)
Introduction	333	(1)
Dehydrohalogenation of Alkyl Halides	334	(10)
Base-Promoted Elimination of an Alkyl Halide	336	(1)
Elimination with Alcoholic Potassium Hydroxide	337	(1)
Miniscale Procedure	337	(1)
Microscale Procedure	337	(2)
Elimination with Potassium tert-Butoxide	339	(1)
Miniscale Procedure	339	(1)
Discovery Experiment	340	(1)
Elimination of Alternate Non-terminal Alkyl Halides	340	(4)
Dehydration of Alcohols	344	(16)
Dehydration of Alcohols	348	(1)
Dehydration of 4-Methyl-2-Pentanol	348	(1)
Miniscale Procedure	348	(1)
Dehydration of Cyclohexanol	349	(1)
Miniscale Procedure	349	(1)
Microscale Procedure	350	(1)
Discovery Experiment	351	(1)
Elimination of Stereoisomeric Alcohols	351	(9)
Addition Reactions of Alkenes: Overview	360	(3)
Addition of Hydrobromic Acid to Alkenes	363	(9)
Addition of Hydrogen Bromide to 1-Hexene	364	(1)
Miniscale Procedure	365	(1)
Microscale Procedure	366	(6)
Bromination of Alkenes	372	(5)
Bromination of (E)-Stilbene	372	(1)
Miniscale Procedure	373	(1)
Microscale Procedure	373	(4)
Acid-Catalyzed Hydration of Alkenes	377	(5)
Hydration of Norbornene	378	(1)
Miniscale Procedure	378	(4)
Hydroboration-Oxidation of Alkenes	382	(13)
Hydroboration-Oxidation of (+)-α-Pinene	385	(1)
Miniscale Procedure	386	(1)
Microscale Procedure	387	(4)
Historical Highlights: Additions Across Carbon-Carbon π-Bonds	391	(4)
Alkynes	395	(16)
Introduction	395	(1)
Dehydrohalogenation of 1,2-Dihaloalkanes	396	(5)
Dehydrobromination of Meso-Stilbene Dibromide	397	(1)
Miniscale Procedure	398	(1)
Microscale Procedure	398	(1)
Miniscale Procedure for Microwave Option	399	(2)
Addition Reactions of Alkynes	401	(7)
Preparation of 3-Methyl-3-hydroxy-2-butanone	404	(1)
Miniscale Procedure	404	(4)
Terminal Alkynes as Acids	408	(3)
Formation of a Silver Acetylide and Its Decomposition	409	(2)
Dienes: The Diels-Alder Reaction	411	(24)
Introduction	411	(1)
Mechanistic and Stereochemical Aspects	412	(2)
Applications of Diels-Alder Reactions	414	(21)
Diels-Alder Reaction	416	(1)
Reaction of 1,3-Butadiene and Maleic Anhydride	416	(1)
Miniscale Procedure	416	(1)
Microscale Procedure	417	(1)
Miniscale Procedure for Microwave Option	417	(1)
Reaction of 1,3-Cyclopentadiene and Maleic Anhydride	418	(1)
Miniscale Procedure	418	(1)
Microscale Procedure	419	(1)
Hydrolysis of Anhydrides	420	(1)
1,4-Cyclohexene-cis-1,2-dicarboxylic Acid	420	(1)
Miniscale Procedure	420	(1)
Microscale Procedure	421	(1)
Bicyclo[2.2.1]hept-5-ene-endo-2,3-dicarboxylic Acid	421	(1)
Miniscale Procedure	421	(1)
Microscale Procedure	422	(1)
Discovery Experiment	422	(1)
Hydrolysis of Anhydrides	422	(10)
Historical Highlights: Discovery of the Diels-Alder Reaction	432	(3)
Kinetic and Thermodynamic Control of a Reaction	435	(16)
Introduction	435	(3)
Formation of Semicarbazones Under Kinetic and Thermodynamic Control	438	(13)
Kinetic and Thermodynamic Control of a Reaction	440	(1)
Preparation of Cyclohexanone Semicarbazone	441	(1)
Preparation of 2-Furaldehyde Semicarbazone	441	(1)
Reactions of Semicarbazide with Cyclohexanone and 2-Furaldehyde in Phosphate Buffer Solution	441	(1)
Reactions of Semicarbazide with Cyclohexanone and 2-Furaldehyde in Bicarbonate Buffer Solution	442	(1)
Tests of Reversibility of Semicarbazone Formation	442	(9)
Nucleophilic Aliphatic Substitution: Preparation of Alkyl Halides	451	(30)
General Concepts	451	(1)
Classification of Nucleophilic Substitution Reactions	452	(2)
Competition Between Substitution and Elimination	454	(1)
Preparation of 1-Bromobutane: An SN2 Reaction	455	(8)
Preparation of 1-Bromobutane	457	(1)
Miniscale Procedure	457	(1)
Microscale Procedure	458	(1)
Discovery Experiment	459	(1)
Analysis of SN Reactions as a Function of Substrate	459	(4)
Preparation of 2-Chloro-2-methybutane: An SN1 Reaction	463	(8)
Preparation of 2-Chloro-2-methylbutane	465	(1)
Miniscale Procedure	465	(1)
Microscale Procedure	466	(1)
Discovery Experiment	467	(1)
Analysis of SN Reactions as a Function of Substrate	467	(4)
Chemical Kinetics: Evidence for Nucleophilic Substitution Mechanisms	471	(10)
Kinetics of Solvolysis of 2-Chloro-2-methylbutane	474	(1)
Miniscale Procedure	475	(2)
Discovery Experiment	477	(1)
Effect of Temperature on Rates of Solvolysis	477	(1)
Effect of Leaving Group on Rates of Solvolysis	477	(4)
Electrophilic Aromatic Substitution	481	(44)
Introduction	481	(1)
Friedel-Crafts Alkylation of p-Xylene with 1-Bromopropane	482	(11)
Friedel-Crafts Alkylation of p-Xylene	485	(1)
Miniscale Procedure	485	(2)
Microscale Procedure	487	(6)
Friedel-Crafts Acylation of m-Xylene	493	(9)
Friedel-Crafts Acylation of m-Xylene with Phthalic Anhydride	495	(1)
Miniscale Procedures	495	(2)
Microscale Procedure	497	(5)
Nitration of Bromobenzene	502	(9)
Nitration of Bromobenzene	504	(1)
Nitration	504	(1)
Miniscale Procedure	504	(1)
Microscale Procedures	505	(1)
Thin-Layer Chromatography	506	(1)
Column Chromatography	507	(1)
Miniscale Procedure	507	(4)
Relative Rates of Electrophilic Aromatic Substitution	511	(14)
Relative Rates of Electrophilic Aromatic Bromination	514	(1)
Qualitative Measurements	514	(1)
Miniscale Procedures	514	(1)
Quantitative Measurements	515	(1)
Miniscale Procedures	515	(7)
Historical Highlights: Discovery of the Friedel-Crafts Reaction	522	(3)
Oxidation of Alcohols and Carbonyl Compounds	525	(26)
Introduction	525	(2)
Preparation of Aldehydes and Ketones by Oxidation of Alcohols	527	(14)
Oxidation of Alcohols	531	(1)
Oxidation of Cyclododecanol to Cyclododecanone	531	(1)
Miniscale Procedure	531	(4)
Oxidation of 4-Chlorobenzyl Alcohol to 4-Chlorobenzoic Acid	535	(1)
Miniscale Procedure	536	(1)
Microscale Procedure	536	(5)
Base-Catalyzed Oxidation-Reduction of Aldehydes: The Cannizzaro Reaction	541	(10)
Base-Catalyzed Oxidation-Reduction of Aldehydes by the Cannizzaro Reaction	543	(1)
Miniscale Procedure	543	(1)
Microscale Procedure	544	(4)
Historical Highlights: Green Chemistry	548	(3)
Reduction Reactions of Double Bonds: Alkenes, Carbonyl Compounds, and Imines	551	(34)
Introduction	551	(2)
Catalytic Hydrogenation of the Carbon-Carbon Double Bond	553	(6)
Hydrogenation of 4-Cyclohexene-cis-1,2-dicarboxylic Acid	555	(1)
Miniscale Procedure	555	(4)
Reduction of Imines; Preparation of Amines	559	(10)
Formation and Reduction of N-Cinnamylidene-m-nitroaniline	561	(1)
Miniscale Procedure	562	(1)
Microscale Procedure	563	(6)
Reduction of Carbonyl Compounds; Preparation of Alcohols	569	(6)
Reduction of 9-Fluorenone	570	(1)
Miniscale Procedure	570	(1)
Microscale Procedure	571	(1)
Discovery Experiment	571	(1)
Reduction of 4-tert-Butylcyclohexanone	571	(1)
Reduction of Benzoin	572	(3)
Enzymatic Reduction: A Chiral Alcohol from a Ketone	575	(6)
Enzymatic Reduction of Methyl Acetoacetate	576	(1)
Miniscale Procedure	576	(5)
Determining Optical Purity	581	(4)
Determining Optical Purity of Methyl (S)-(+)-3-Hydroxybutanoate	582	(3)
Reactions of Carbonyl Compounds	585	(38)
Introduction	585	(2)
The Wittig and Related Reactions	587	(14)
Wittig and Wadsworth-Emmons Reactions	590	(1)
Synthesis of (Z)- and (E)-Stilbenes by a Wittig Reaction	590	(1)
Miniscale Procedure	590	(1)
Microscale Procedure	591	(2)
Discovery Experiment	593	(1)
Wittig Reaction of 9-Anthraldehyde	593	(1)
Synthesis of a Stilbene by the Wadsworth-Emmons Reaction	594	(1)
Miniscale Procedure	594	(1)
Microscale Procedure	595	(6)
Reactions of Stabilized Carbanions from Carbonyl Compounds	601	(8)
Synthesis of trans-p-Anisalacetophenone	603	(1)
Miniscale Procedure	603	(1)
Microscale Procedure	604	(1)
Discovery Experiment	605	(1)
Synthesis of trans, trans-Dibenzylideneacetone	605	(4)
Conjugate Addition to an α,β-Unsaturated Ketone	609	(14)
Preparation of 4,4-Dimethyl-2-cyclohexen-1-one	612	(1)
Miniscale Procedure	612	(1)
Microscale Procedure	613	(7)
Historical Highlights: The Wittig Reaction	620	(3)
Organometallic Chemistry	623	(28)
Introduction	623	(1)
Grignard Reagents: Preparation	624	(9)
Preparation of Grignard Reagents	627	(1)
Miniscale Procedure	628	(1)
Microscale Procedure	629	(4)
Grignard Reagents: Reactions	633	(2)
Special Experimental Techniques	635	(16)
Reactions of Grignard Reagents	636	(1)
Preparation of Triphenylmethanol	636	(1)
Miniscale Procedure	636	(1)
Microscale Procedure	637	(2)
Preparation of Benzoic Acid	639	(1)
Miniscale Procedure	639	(1)
Microscale Procedure	640	(2)
Preparation of 2-Methyl-3-heptanol	642	(1)
Miniscale Procedure	642	(8)
Historical Highlights: Grignard and the Beginnings of Modern Organometallic Chemistry	650	(1)
Carboxylic Acids and Their Derivatives	651	(34)
Introduction	651	(3)
Esters and the Fischer Esterification	654	(7)
Preparation of Benzocaine	655	(1)
Miniscale Procedure	655	(1)
Miniscale Procedure for Microwave Option	656	(1)
Microscale Procedure	657	(4)
Amides and Insect Repellents	661	(10)
Preparation of N,N-Diethyl-m-toluamide	664	(1)
Miniscale Procedure	664	(2)
Microscale Procedure	666	(5)
Amides and Chemiluminescence	671	(14)
Preparation and Chemiluminescence of Luminol	676	(1)
Preparation of Luminol	676	(1)
Miniscale Procedure	676	(1)
Microscale Procedure	677	(1)
Chemiluminescence	677	(1)
Miniscale Procedure	677	(1)
Microscale Procedure	678	(4)
Historical Highlights: Evolution of Man-Made Analgesics	682	(3)
Multistep Organic Synthesis	685	(64)
Introduction	685	(1)
Sulfanilamide: Discovery and Synthesis of the First Antibiotic	686	(22)
Synthesis of Sulfanilamide	693	(1)
Preparation of Aniline	693	(1)
Miniscale Procedure	694	(1)
Preparation of Acetanilide	695	(1)
Miniscale Procedure	695	(1)
Preparation of 4-Acetamidobenzenesulfonyl Chloride	696	(1)
Miniscale Procedure	697	(1)
Preparation of 4-Acetamidobenzenesulfonamide	698	(1)
Miniscale Procedure	698	(1)
Preparation of Sulfanilamide	699	(1)
Miniscale Procedure	699	(9)
Synthesis of 1-Bromo-3-Chloro-5-iodobenzene	708	(21)
Synthesis of 1-Bromo-3-Chloro-5-iodobenzene	713	(1)
Preparation of Aniline and Acetanilide	713	(1)
Preparation of 4-Bromoacetanilide	713	(1)
Miniscale Procedure	714	(1)
Microscale Procedure	714	(1)
Preparation of 4-Bromo-2-chloroacetanilide	715	(1)
Miniscale Procedure	715	(1)
Microscale Procedure	715	(1)
Preparation of 4-Bromo-2-chloroaniline	716	(1)
Miniscale Procedure	716	(1)
Microscale Procedure	717	(1)
Preparation of 4-Bromo-2-chloro-6-iodoaniline	718	(1)
Miniscale Procedure	718	(1)
Microscale Procedure	718	(1)
Preparation of 4-Bromo-2-chloro-6-iodobenzene	719	(1)
Miniscale Procedure	719	(1)
Microscale Procedure	720	(9)
Lidocaine: Synthesis of an Anesthetic Agent	729	(20)
Synthesis of Lidocaine	733	(1)
Preparation of 2,6-Dimethylaniline	733	(1)
Miniscale Procedure	733	(1)
Microscale Procedure	734	(1)
Preparation of α-Chloro-2,6-dimethylacetanilide	735	(1)
Miniscale Procedure	735	(1)
Microscale Procedure	736	(1)
Preparation of Lidocaine	736	(1)
Miniscale Procedure	737	(1)
Microscale Procedure	738	(7)
Historical Highlights: Discovery of Sulfa Drugs	745	(4)
Polymers	749	(22)
Introduction	749	(2)
Chain-Reaction Polymerization	751	(9)
Preparation of Polystyrene	754	(1)
Miniscale Procedure	754	(1)
Removal of the Inhibitor from Commercial Styrene	754	(1)
Polymerization of Pure Styrene	755	(1)
Solution Polymerization of Styrene	755	(1)
Discovery Experiment	756	(1)
Stability of Polystyrene Toward Organic Solvents	756	(1)
Polymers and Water	756	(1)
Cross-Linking of Polymers	756	(4)
Step-Growth Polymerization	760	(11)
Preparation of Nylon-6,10	764	(1)
Miniscale Procedure	764	(1)
Alternative Procedure	765	(4)
Historical Highlights: Discovery of Polyethylene and Nylon	769	(2)
Carbohydrates	771	(16)
Introduction	771	(1)
Monosaccharides: General Principles	772	(1)
Disaccharides: Hydrolysis of Sucrose	773	(5)
Hydrolysis of Sucrose	775	(1)
Miniscale Procedure	775	(3)
Carbohydrates: Their Characterization and Identification	778	(9)
Classification Tests for Carbohydrates	779	(1)
Microscale Procedure	779	(3)
Formation of Osazones	782	(1)
Microscale Procedure	782	(1)
Historical Highlights: Emil Fischer: Carbohydrate Chemist Extraordinaire	783	(4)
α-Amino Acids and Peptides	787	(30)
Introduction	787	(3)
Synthesis of Peptides and Polypeptides	790	(1)
Synthesis of the Protected Dipeptide Ala---Phe---OMe	791	(26)
Preparation of N-tert-Butoxycarbonyl L-Alanine	795	(1)
Miniscale Procedure	795	(1)
Microscale Procedure	796	(1)
Preparation of Methyl L-Phenylalaninate Hydrochloride	797	(1)
Miniscale Procedure	798	(1)
Microscale Procedure	798	(1)
Preparation of Methyl N-tert-Butoxycarbonyl L-Alanyl-L-phenylalaninate	799	(1)
Miniscale Procedure	799	(1)
Microscale Procedure	800	(1)
Preparation of Methyl L-Alanylphenyl-L-alaninate Trifluoroacetate	801	(1)
Miniscale Procedure	802	(1)
Microscale Procedure	802	(1)
Discovery Experiment	803	(1)
Synthesis of L-Alanyl-L-phenylalanine	803	(9)
Historical Highlights: Invention of a Method for Solid-Phase Peptide Synthesis	812	(5)
Identifying Organic Compounds	817	(72)
Introduction	817	(1)
Overview of Organic Analysis	818	(1)
Classic Qualitative Analysis Procedure to Identify a Pure Compound	819	(12)
Elemental Analysis	821	(1)
Sodium Fusion	822	(1)
Sodium-lead Alloy Method	822	(1)
Sodium Metal Method	822	(1)
Qualitative Analysis for Halogens, Sulfur, and Nitrogen	823	(8)
Separating Mixtures of Organic Compounds	831	(3)
Separating Mixtures on the Basis of Solubility	832	(2)
Applying Spectroscopic Methods to Qualitative Organic Analysis	834	(6)
Qualitative Classification Tests and Preparation of Derivatives	840	(1)
Aldehydes and Ketones	840	(11)
2,4-Dinitrophenylhydrazine Test for Aldehydes and Ketones	841	(2)
Schiff's Test for Aldehydes	843	(1)
Tollens' Test for Aldehydes	844	(1)
Chromic Acid Test for Aldehydes and 1° and 2° Alcohols	845	(3)
Iodoform Test	848	(1)
Preparation of Semicarbazones	849	(1)
Preparation of Oximes	850	(1)
Alkenes and Alkynes	851	(2)
Bromine Test for Unsaturation	851	(2)
Baeyer Test for Unsaturation	853	(1)
Alkyl Halides	853	(3)
Silver Nitrate Test for Alkyl Halides	854	(1)
Sodium Iodide Test for Alkyl Chlorides and Bromides	855	(1)
Aromatic Hydrocarbons and Aryl Halides	856	(5)
Friedel-Crafts Reaction for Detecting Arenes	857	(1)
Preparation of Nitroarenes	858	(1)
Side-Chain Oxidation of Arenes	859	(2)
Alcohols	861	(5)
Lucas Test for Alcohols	862	(1)
Preparation of Urethanes	863	(1)
Preparation of 3,5-Dinitrobenzoates	864	(2)
Phenols	866	(4)
Bromine Water Test for Phenols	867	(1)
Ceric Nitrate Test for Alcohols and Phenols	868	(1)
Ferric Chloride Test for Phenols and Enols	868	(1)
Preparation of Bromophenols	869	(1)
Carboxylic Acids	870	(3)
Determination of Equivalent Mass of an Acid	870	(1)
Preparation of Amides	871	(2)
Amines	873	(6)
Hinsberg Test for Amines	875	(2)
Ramini and Simon Tests for Amines	877	(1)
Preparation of Benzamides, Benzenesulfonamides, and Methiodides	878	(1)
Nitro Compounds	879	(2)
Hydroxide Test for Nitro Compounds	880	(1)
Reduction of Nitro Compounds	880	(1)
Esters	881	(4)
Hydroxylamine Test for Esters	882	(1)
Determination of Saponification Equivalent	883	(1)
Base-Promoted Hydrolysis of Esters	884	(1)
Nitriles	885	(2)
Hydroxylamine Test for Nitriles	885	(1)
Hydrolysis of Nitriles	886	(1)
Amides	887	(2)
Base-Promoted Hydrolysis of Amides	888	(1)
The Literature of Organic Chemistry	889	(20)
Introduction	889	(1)
Classification of the Literature	889	(13)
Using the Literature of Organic Chemistry	902	(7)
Index	909