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9780582462366

Vogel's Textbook of Practical Organic Chemistry

by ; ; ; ;
  • ISBN13:

    9780582462366

  • ISBN10:

    0582462363

  • Edition: 5th
  • Format: Hardcover
  • Copyright: 1996-02-09
  • Publisher: Pearson

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Supplemental Materials

What is included with this book?

Summary

Most widely used, established and respected reference manual for the organic chemistry laboratory. Incorporates new reactions and techniques now available to the organic chemist.

Table of Contents

Organic Synthesis
1(26)
Introduction
1(1)
Structure of the Target Molecule
2(8)
Reaction Mechanism and the Methodology of Synthesis
10(7)
Reaction Mechanism and the Strategy of Synthesis
17(6)
Conclusion
23(3)
References
23(3)
Experimental Techniques
26(228)
General Instructions for Safe Working in Organic Chemical Laboratories
26(5)
Planning of Experiments and Recording of Results
31(3)
Hazards in Organic Chemistry Laboratories
34(18)
Introduction
34(1)
Explosion and fire hazards
35(7)
Reactive inorganic reagents
42(2)
Hazards due to toxic chemicals
44(7)
Electrical safety
51(1)
Ultraviolet radiation
52(1)
Apparatus and Reaction Procedures
52(1)
Interchangeable Ground Glass Joints
52(3)
Types of Ground Glass Joints
55(2)
Care and Maintenance of Ground Glass Joints
57(1)
Apparatus With Interchangeable Ground Glass Joints Suitable for General Use in Preprative Organic Chemistry
58(5)
Other Types of Interchangeable Joints and Stopcocks
63(1)
The Use of Corks and Rubber Stoppers
64(1)
Cutting and Bending of Glass Tubing
65(1)
General Laboratory Apparatus
66(4)
Cooling of Reaction Mixtures
70(1)
Heating of Reaction Mixtures
71(2)
Mechanical Agitation
73(7)
Typical Ground Glass Joint Assemblies for Standard Reaction Procedures
80(6)
Precautions for Unattended Reactions
86(1)
Apparatus for Special Reaction Techniques
87(44)
Catalytic hydrogenation
87(10)
Reactions under pressure
97(2)
Uncatalysed and catalysed vapour phase reactions
99(4)
Ozonolysis
103(3)
Organic photochemistry
106(9)
Electrolytic (anodic) syntheses
115(1)
Liquid ammonia techniques
116(4)
Reactions involving air-sensitive compounds
120(11)
Isolation and Purification Processes
131(1)
General Considerations
131(2)
Filtration Techniques
133(2)
Recrystallisation Techniques
135(18)
Sublimation Techniques -- Freeze Drying
153(3)
Solvent Extraction
156(9)
Drying of Liquids or of Solutions of Organic Compounds in Organic Solvents
165(4)
Distillation at Atmospheric Pressure
169(2)
Steam Distillation
171(2)
Fractional Distillation at Atmospheric Pressure
173(8)
Distillation Under Diminished Pressure (`Vacuum' Distillation)
181(5)
High Vacuum Distillation -- Molecular Distillation
186(5)
Vacuum Pumps
191(2)
Manometers, Vacustats, Vacuum Gauges and Manostats
193(4)
Chromatography
197(37)
Storage of Samples
234(2)
Determination of Physical Constants
236(1)
Melting Point -- Mixed Melting Points
236(5)
Determination of Boiling Point
241(2)
Determination of Molecular Weight
243(1)
Determination of Optical Rotatory Power
244(5)
Determination of Refractive Index
249(5)
References
250(4)
Spectroscopic Methods and the Interpretation of Spectra
254(141)
Introduction
254(1)
The electromagnetic spectrum
255(1)
Infrared Spectroscopy
256(60)
Instrumental features of infrared spectrophotometers
258(1)
Determination of infrared spectra
259(1)
Sample preparation
260(8)
Features of an infrared spectrum
268(3)
Interpretation of an infrared spectrum
271(2)
Characteristic group frequencies
273(43)
Nuclear Magnetic Resonance Spectroscopy
316(45)
Features of the nuclear magnetic resonance spectrum
319(5)
The chemical shift
324(14)
Spin-spin splitting
338(10)
Protons attached to heteroatoms
348(2)
Simplification of 1H spectra
350(9)
Interpretation of the p.m.r. spectrum
359(1)
Further information from 13C-spectra
360(1)
Mass Spectrometry
361(22)
The mass spectrum
362(10)
Appearance of the mass spectrum
372(1)
Interpretation of the mass spectrum
373(1)
Mass spectra of classes of organic compounds
373(10)
Ultraviolet--Visible Spectroscopy
383(12)
Instrumental features of ultraviolet--visible spectrophotometers
384(1)
Determination of ultraviolet--visible spectra
384(1)
Laws of light absorption
385(1)
Solvents for ultraviolet spectroscopy
386(1)
Solution preparation
386(1)
Optical cells and their care
387(1)
Features of an ultraviolet--visible spectrum
388(5)
References
393(2)
Solvents and Reagents
395(75)
The Purification of Common Organic Solvents
395(18)
Saturated aliphatic hydrocarbons
397(1)
Aromatic hydrocarbons
398(1)
Halogenated hydrocarbons
399(1)
Aliphatic alcohols
400(4)
Ethers
404(3)
Ketones
407(2)
Esters
409(1)
Nitrogen-containing solvents
409(2)
Sulphur-containing solvents
411(1)
Phosphorus-containing solvents
412(1)
The Preparation and Purification of Reagents
413(57)
References
468(2)
Aliphatic Compounds
470(354)
Alkanes
470(14)
Structure
470(1)
Summary of preparative methods and of retrosynthetic strategies
471(1)
Spectroscopic features
472(1)
The catalytic hydrogenation and chemical reduction of alkenes
472(2)
The hydrolysis of alkylmagnesium halides and the hydrogenolysis of alkyl halides and of alkyl methane- or toluene-p-sulphonates
474(2)
The reduction of aldehydes and ketones
476(1)
Coupling reactions (a) using organometallic compounds, and (b) at the anode
477(7)
Alkenes
484(23)
Structure
484(1)
Summary of preparative methods and of retrosynthetic strategies
485(1)
Spectroscopic features
486(1)
1,2-Elimination processes (β-elimination)
486(7)
The partial hydrogenation of alkynes
493(2)
Wittig and related reactions
495(9)
Selected rearrangements of alkynes to allenes
504(3)
Alkynes
507(10)
Structure
507(1)
Summary of preparative methods and of retrosynthetic strategies
508(1)
Spectroscopic features
508(1)
The dehydrogenation of vic- and gem-dihalides
509(3)
The oxidation of dihydrazones of 1,2-diketones
512(1)
Alkylation of a terminal alkyne
513(2)
Coupling reactions leading to diynes
515(2)
Aliphatic Alcohols
517(36)
Structure
517(1)
Summary of preparative methods and of retrosynethetic strategies
517(2)
Spectroscopic features
519(1)
The reduction of aldehydes, ketones, and esters
519(12)
The interaction of carbonyl-containing compounds with organometallic reagents
531(11)
The hydroboration-oxidation of alkenes
542(3)
The oxymercuration-demercuration of alkenes
545(2)
The hydroxylation of alkenes
547(3)
Methods for the protection of the hydroxyl group
550(3)
Aliphatic Halides
553(26)
Structure
553(1)
Summary of preparative methods and of retrosynthetic strategies
554(1)
Spectroscopic features
554(1)
Preparation of alkyl chlorides from alcohols
555(4)
Preparation of alkyl bromides from alcohols
559(7)
Preparation of alkyl iodides from alcohols
566(4)
Displacement reactions involving a halogen atom
570(2)
Displacement reactions involving a methanesulphonyloxy group
572(2)
Displacement reactions involving the amino group
574(1)
Addition of hydrogen halides or halogens to alkenes
574(3)
The replacement of reactive allylic hydrogen atoms by bromine
577(2)
Aliphatic Ethers
579(6)
Structure
579(1)
Summary of preparative methods and of retrosynthetic strategies
580(1)
Spectroscopic features
580(1)
The formation of ethers from alcohols under acidic conditions
581(2)
The interaction of an alcohol with a halogen compound under basic conditions
583(2)
Aliphatic Aldehydes
585(19)
Structure
585(1)
Summary of preparative methods and of retrosynthetic strategies
585(2)
Spectroscopic features
587(1)
The controlled oxidation or dehydrogenation of primary alcohols
587(3)
The oxidative cleavage of 1,2-diols
590(2)
The ozonolysis of suitably substituted alkenes
592(2)
The reduction of nitriles, carboxylic acids and carboxylic acid chlorides
594(2)
Methods based upon alkyl halides
596(2)
The hydrolysis and decarboxylation of α,β-epoxy esters (glycidic esters)
598(1)
The oxidative hydrolysis of nitronate salts derived from primary nitroalkanes
599(1)
Methods for the alkylation of the carbon chain
600(4)
Aliphatic Ketones
604(22)
Structure
604(1)
Summary of preparative methods and of retrosynthetic strategies
605(1)
Spectroscopic features
606(1)
The oxidation of secondary alcohols
607(5)
The hydration of alkynes
612(1)
The thermal decarboxylation of acids over a metal oxide catalyst
612(4)
The interaction of organometallic compounds with carboxylic acid chlorides and N,N-dimethylcarboxamides
616(3)
The hydrolysis and decarboxylation of β-keto esters and the hydrolysis of β-diketones
619(4)
The acid-catalysed rearrangement of 1,2-diols
623(1)
The oxidative hydrolysis of nitronate salts from secondary nitroalkanes
623(1)
Methods for the protection of the carbonyl group in aldehydes and ketones
623(3)
Dicarbonyl Compounds
626(11)
Structure
626(1)
1,2-Dicarbonyl compounds
627(5)
1,3-Dicarbonyl compounds
632(3)
1,4-Dicarbonyl compounds
635(2)
Carbohydrates
637(27)
Structure
637(5)
Carbohydrate interconversions
642(2)
Carbohydrate interconversions
644(7)
Carbohydrate interconversions
651(7)
Carbohydrate interconversions
658(2)
Carbohydrate interconversions
660(4)
Aliphatic Carboxylic Acids
664(27)
Structure
664(1)
Summary of preparative methods and of retrosynthetic strategies
664(2)
Spectroscopic features
666(1)
Oxidative methods
667(4)
Hydrolysis of alkyl cyanides
671(2)
Carboxylation of Grignard reagents
673(2)
The Arndt-Eistert method
675(2)
Electrolytic (anodic) coupling
677(3)
Methods utilising diethyl malonate
680(7)
The synthesis of optically active carboxylic acids
687(3)
Methods for the protection of the carboxyl group
690(1)
Carboxylic Acid Derivatives
691(19)
Structure
691(1)
Summary of retrosynthetic strategies
692(1)
Spectroscopic features
692(1)
Acyl halides
692(1)
Acid anhydrides
693(2)
Esters
695(13)
Acid amides
708(2)
Aliphatic Nitriles
710(9)
Summary of preparative methods and of retrosynthetic strategies
710(1)
Spectroscopic features
711(1)
Displacement with cyanide ion on an alkyl halide
711(1)
Displacement with cyanide ion on an arylsulphonylhydrazone
712(3)
Dehydration of amides and aldoximes
715(2)
Cyanoethylation procedures and the α-alkylation of nitriles
717(2)
Substituted Carboxylic Acids and Their Derivatives
719(44)
Structure
719(1)
Spectroscopic features
720(1)
Halogeno acids
720(5)
Hydroxy acids and lactones
725(10)
Keto acids and esters
735(11)
Amino acids and peptides
746(17)
Nitroalkanes
763(6)
Structure
763(1)
Summary of preparative methods and of retrosynthetic strategies
764(1)
Spectroscopic features
764(1)
The displacement of a halogen by a nitrite ion in an alkyl halide
764(1)
The oxidation of oximes and amines
765(3)
C-Alkylation of nitroalkanes and other homologation procedures
768(1)
Aliphatic Amines
769(17)
Structure
769(1)
Summary of preparative methods and of retrosynthetic strategies
770(1)
Spectroscopic features
771(1)
The reduction of alkyl azides, alkyl cyanides and amides
771(3)
The reduction of nitro compounds and oximes
774(2)
The reductive alkylation of ammonia or amines
776(3)
The alkylation of ammonia and its derivatives
779(3)
Imine and enamine formation
782(1)
Molecular rearrangements of the Hofmann type
783(1)
Methods for the protection of the amino and imino groups
784(2)
Aliphatic Sulphur Compounds
786(8)
Structure
786(1)
Spectroscopic features
787(1)
Thiols and thioacetals
787(2)
Dialkyl sulphides (thioethers) and trialkylsulphonium salts
789(2)
Sulphoxides and sulphones
791(1)
O,S-Dialkyl dithiocarbonates (xanthate esters)
792(2)
Unsaturated Compounds
794(15)
Unsaturated alcohols
794(4)
Unsaturated carbonyl compounds
798(6)
Unsaturated acids and esters
804(5)
Resolution of Racemates
809(15)
References
816(8)
Aromatic Compounds
824(263)
Aromatic Hydrocarbons
824(26)
Structure
824(1)
Spectroscopic features
825(1)
Alkylbenzenes
826(7)
Di- and triarylmethanes
833(2)
Biphenyl systems
835(4)
Condensed polycyclic systems
839(8)
Some non-benzenoid systems
847(3)
Aromatic Nitro Compounds
850(8)
Summary of preparative methods and of retrosynthetic strategies
850(1)
Spectroscopic features
851(1)
Direct nitration
851(6)
The oxidation of amines
857(1)
The replacement of a diazo group by a nitro group
858(1)
Aromatic Halogen Compounds
858(14)
Structure
858(1)
Summary of preparative methods and of retrosynthetic strategies
858(1)
Spectroscopic features
859(1)
Direct halogenation
860(5)
Chloromethylation
865(2)
The replacement of a diazo group by a halogen
867(1)
The replacement of a hydroxyl group by a halogen
867(1)
Methods leading to polyvalent iodine compounds
868(4)
Aromatic Sulphonic Acids and Their Derivatives
872(16)
Structure
872(1)
Summary of preparative methods and of retrosynthetic strategies
872(1)
Spectroscopic features
873(1)
Direct sulphonation
873(4)
The preparation of arylsulphonyl chlorides
877(2)
The preparation of arylsulphonamides
879(4)
The preparation of arylsulphonate esters
883(4)
Reduction products from arylsuphonyl chlorides
887(1)
Aromatic Amines
888(18)
Structure
888(1)
Summary of preparative methods and of restrosynthetic strategies
889(1)
Spectroscopic features
890(2)
The reduction of nitro compounds
892(5)
Molecular rearrangements of the Hofmann type
897(3)
The replacement of halogen by an amino group
900(1)
The replacement of a phenolic hydroxyl group by an amino group
900(1)
Alkylation and reductive alkylation procedures
901(5)
Some methods for the protection of the amino and imino groups
906(1)
Substitution Products of Aromatic Amines
906(14)
Nuclear substitution products
906(10)
Acylated amines and their substitution reactions
916(4)
Formation of Diazonium Salts and Their Uses
920(33)
Reactions involving replacement of the diazo group
922(24)
Coupling reactions
946(7)
Miscellaneous Aromatic Nitrogen Compounds
953(15)
Intermediate products in the reduction of nitro compounds
953(6)
Arylhydrazines
959(4)
Arylureas and related compounds
963(5)
Phenols and Phenyl Ethers
968(21)
Summary of preparative methods and of retrosynthetic strategies
968(1)
Spectroscopic features
969(1)
Methods for the introduction of a hydroxyl group into an aromatic ring
970(5)
Substitution reactions of phenols
975(9)
Formation of phenyl ethers
984(4)
Some methods for the protection of the phenolic hydroxyl group
988(1)
Aromatic Aldehydes
989(16)
Summary of preparative methods and of retrosynthetic strategies
989(1)
Spectroscopic features
990(1)
Aromatic formylation reactions
990(9)
Reactions involving modification of aromatic ring substituents
999(6)
Aromatic Ketones and Quinones
1005(23)
Summary of preparative methods and of retrosynthetic strategies for aromatic ketones
1005(1)
Spectroscopic features
1005(1)
Friedel-Crafts-type acylation processes
1006(2)
Synthesis of aromatic ketones from carboxylic acid derivatives
1008(11)
Quinones
1019(9)
Some Reactions of Aromatic Carbonyl Compounds
1028(28)
The Cannizzaro reaction
1028(4)
The Claisen-Schmidt and related reactions
1032(4)
The Perkin and Doebner reactions
1036(5)
The synthesis of diphenylpolyenes
1041(2)
The benzion condensation
1043(4)
Oxime formation
1047(3)
Some reactions of alkyl aryl ketones
1050(6)
Methods for the protection of the aromatic carbonyl group
1056(1)
Aromatic Carboxylic Acids
1056(17)
Summary of preparative methods and of retrosynthetic strategies
1056(1)
Spectroscopic features
1057(1)
Oxidative methods
1057(5)
The hydrolysis of nitriles
1062(5)
Carboxylation of the aromatic ring system
1067(4)
Nuclear nitration of aromatic carboxylic acids and esters
1071(1)
Some methods for the protection of the carboxyl group
1072(1)
Aromatic Carboxylic Acid Derivatives
1073(8)
Structure
1073(1)
Spectroscopic features
1073(1)
Acid halides
1073(1)
Acid anhydrides
1074(2)
Esters
1076(4)
Acid amides
1080(1)
Aromatic Nitriles
1081(6)
Summary of preparative methods and of retrosynthetic strategies
1081(1)
The Sandmeyer procedure
1081(1)
The displacement of halogen by cyanide in an aryl halide
1082(1)
The dehydration of amides and aldoximes
1082(3)
References
1085(2)
Selected Alicyclic Compounds
1087(40)
Intramolecular Nucleophilic Displacement Reactions
1087(5)
Intramolecular Addition Reactions of Carbonions to a Carbonyl Group
1092(14)
Insertion Reactions
1106(5)
Ring Expansion and Ring Contraction Reactions
1111(3)
Reduction of Aromatic Compounds
1114(3)
Cycloaddition Reactions
1117(10)
References
1126(1)
Selected Heterocyclic Compounds
1127(69)
Three-Membered Heterocycles
1127(11)
Intramolecular cyclisation of a 1,2-bifunctional compound
1128(3)
Insertion of a methylene group into a carbon-heteroatom double bond
1131(1)
Insertion of a heteroatom into a carbon-carbon double bond
1132(5)
Heteroatom exchange
1137(1)
Four-Membered Heterocycles
1138(6)
Cyclisation reactions
1138(3)
Cycloaddition reactions
1141(3)
Five-Membered Heterocycles
1144(20)
Pyrroles, furans, thiophenes and pyrazolones from dicarbonyl compounds
1146(5)
Hydantoins from urea, and thiazoles from thiourea or thioamides
1151(4)
Oxazolones (and azlactones) from α-amino acids
1155(1)
Indoles, benzofurans and benzothiophenes
1156(6)
Benzimidazoles and benzotriazole from o-phenylene diamine
1162(2)
Six-Membered Heterocycles
1164(32)
Pyridines and pyrylium salts
1165(7)
Pyrones and pyridones
1172(2)
Barbituric acid and barbiturates
1174(6)
Quinolines, isoquinolines and quinoxalines
1180(10)
Coumarins and chromones
1190(4)
References
1194(2)
Investigation and Characterisation of Organic Compounds
1196(102)
Physical Constants
1197(1)
The Study of Solubility Behaviour
1198(6)
Detection of Elements Present
1204(6)
Spectroscopic Information
1210(1)
Functional Group Identification
1211(23)
Acidic compounds
1211(4)
Basic compounds
1215(3)
Neutral compounds
1218(16)
Preparation of Derivatives
1234(53)
Saturated aliphatic hydrocarbons
1235(1)
Unsaturated aliphatic hydrocarbons
1235(3)
Aromatic hydrocarbons
1238(3)
Alcohols and polyhydric alcohols
1241(4)
Carbohydrates
1245(3)
Phenols
1248(3)
Enols
1251(1)
Aliphatic halogen compounds
1251(2)
Aromatic halogen compounds
1253(1)
Aliphatic ethers
1254(1)
Aromatic ethers
1255(2)
Acetals
1257(1)
Aldehydes and ketones
1257(4)
Quinones
1261(1)
Carboxylic acids
1261(4)
Carboxylic acid chlorides and anhydrides
1265(1)
Esters
1266(4)
Primary amides
1270(1)
Substituted amides
1271(1)
Nitriles
1271(2)
Primary and secondary amines
1273(5)
Tertiary amines
1278(1)
α-Amino acids
1279(2)
Nitro compounds
1281(2)
Thiols
1283(1)
Sulphonic acids
1284(2)
Sulphonamides
1286(1)
Separation of Mixtures of Organic Compounds
1287(11)
Introduction
1287(3)
Preliminary examination of a mixture
1290(2)
Separation of water-insoluble mixtures
1292(3)
Separation of water-soluble mixtures
1295(3)
Physical Constants of Organic Compounds
1298(156)
Tables of derivatives
1298(1)
Index to tables
1298(103)
APPENDICES
1. The Literature of Organic Chemistry
1401(11)
2. Infrared Correlation Tables
1412(11)
3. Nuclear Magnetic Resonance Correlation Tables
1423(12)
4. Mass Spectrometry Correlation Tables
1435(7)
5. Useful Solvent Characteristics: Hazard Symbols
1442(5)
6. Common Synthons and Their Reagent Equivalents
1447(4)
7. Selection of Manufacturers and Suppliers of Laboratory Apparatus, Equipment and Chemicals
1451(3)
Table of atomic weights 1454(1)
Index 1455(56)
References data 1511(2)
Abbreviations 1513

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