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Experimental Organic Chemistry : A Miniscale and Microscale Approach,9780495013341
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Experimental Organic Chemistry : A Miniscale and Microscale Approach

by
Edition:
4th
ISBN13:

9780495013341

ISBN10:
049501334X
Media:
Hardcover
Pub. Date:
11/11/2005
Publisher(s):
Cengage Learning
List Price: $319.33

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What version or edition is this?
This is the 4th edition with a publication date of 11/11/2005.
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  • The New copy of this book will include any supplemental materials advertised. Please check the title of the book to determine if it should include any CDs, lab manuals, study guides, etc.

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


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