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Organic Chemistry

ISBN: 9780131478718 | 0131478710
Edition: 6th
Format: Hardcover
Publisher: Prentice Hall
Pub. Date: 1/1/2006

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SummaryTable of Contents
In a highly accessible fashion, this top-selling book bridges the gap between conceptual understanding and actual applicationwhile strongly emphasizing the development of problem-solving skills. The book focuses on traditional organic chemistry topics and offers up-to-date aspects of spectroscopy, relevant photographs, and many applications to polymer chemistry integrated throughout the book.
For two-semester courses in Organic Chemistry taken primarily by science and pre-health majors. Wade, organized around funct... MORE
Prefacexxiii
About the Authorxli
1 Introduction and Review1(38)
1-1 The Origins of Organic Chemistry
1(2)
... MORE
1-2 Principles of Atomic Structure
3(3)
1-3 Bond Formation: The Octet Rule
6(1)
1-4 Lewis Structures
7(1)
1-5 Multiple Bonding
8(1)
Summary: Common Bonding Patterns (Uncharged)
9(1)
1-6 Electronegativity and Bond Polarity
9(2)
1-7 Formal Charges
11(1)
1-8 Ionic Structures
12(1)
Summary: Common Bonding Patterns in Organic Compounds and Ions
13(1)
1-9 Resonance
13(4)
1-10 Structural Formulas
17(3)
1-11 Molecular Formulas and Empirical Formulas
20(1)
1-12 Arrhenius Acids and Bases
21(1)
1-13 Bransted-Lowry Acids and Bases
22(7)
1-14 Lewis Acids and Bases
29(3)
Chapter 1 Glossary
32(2)
Study Problems
34(5)
2 Structure and Properties of Organic Molecules39(42)
2-1 Wave Properties of Electrons in Orbitals
39(2)
2-2 Molecular Orbitals
41(3)
2-3 Pi Bonding
44(1)
2-4 Hybridization and Molecular Shapes
45(4)
2-5 Drawing Three-Dimensional Molecules
49(1)
2-6 General Rules of Hybridization and Geometry
50(4)
2-7 Bond Rotation
54(2)
2-8 Isomerism
56(2)
2-9 Polarity of Bonds and Molecules
58(3)
2-10 Intermolecular Forces
61(4)
2-11 Polarity Effects on Solubilities
65(3)
2-12 Hydrocarbons
68(3)
2-13 Organic Compounds Containing Oxygen
71(2)
2-14 Organic Compounds Containing Nitrogen
73(2)
Chapter 2 Glossary
75(2)
Study Problems
77(4)
3 Structure and Stereochemistry of Alkanes81(44)
3-1 Classification of Hydrocarbons (Review)
81(1)
3-2 Molecular Formulas of Alkanes
82(1)
3-3 Nomenclature of Alkanes
83(6)
Summary: Rules for Naming Alkanes
88(1)
3-4 Physical Properties of Alkanes
89(2)
3-5 Uses and Sources of Alkanes
91(2)
3-6 Reactions of Alkanes
93(1)
3-7 Structure and Conformations of Alkanes
94(4)
3-8 Conformations of Butane
98(2)
3-9 Conformations of Higher Alkanes
100(1)
3-10 Cycloalkanes
100(3)
3-11 cis-trans Isomerism in Cycloalkanes
103(1)
3-12 Stabilities of Cycloalkanes; Ring Strain
103(4)
3-13 Cyclohexane Conformations
107(4)
3-14 Conformations of Monosubstituted Cyclohexanes
111(3)
3-15 Conformations of Disubstituted Cyclohexanes
114(3)
3-16 Bicyclic Molecules
117(2)
Chapter 3 Glossary
119(3)
Study Problems
122(3)
4 The Study of Chemical Reactions125(42)
4-1 Introduction
125(1)
4-2 Chlorination of Methane
125(1)
4-3 The Free-Radical Chain Reaction
126(4)
Key Mechanism: Free-Radical Halogenation
128(2)
4-4 Equilibrium Constants and Free Energy
130(3)
4-5 Enthalpy and Entropy
133(1)
4-6 Bond-Dissociation Enthalpies
134(1)
4-7 Enthalpy Changes in Chlorination
135(2)
4-8 Kinetics and the Rate Equation
137(2)
4-9 Activation Energy and the Temperature Dependence of Rates
139(1)
4-10 Transition States
140(2)
4-11 Rates of Multistep Reactions
142(1)
4-12 Temperature Dependence of Halogenation
143(1)
4-13 Selectivity in Halogenation
144(5)
4-14 The Hammond Postulate
149(4)
4-15 Radical Inhibitors
153(2)
4-16 Reactive Intermediates
155(5)
Summary: Reactive Intermediates
160(1)
Chapter 4 Glossary
160(3)
Study Problems
163(4)
5 Stereochemistry167(45)
5-1 Introduction
167(1)
5-2 Chirality
168(6)
5-3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms
174(5)
5-4 Optical Activity
179(5)
5-5 Biological Discrimination of Enantiomers
184(1)
5-6 Racemic Mixtures
185(1)
5-7 Enantiomeric Excess and Optical Purity
186(1)
5-8 Chirality of Conformationally Mobile Systems
187(2)
5-9 Chiral Compounds without Asymmetric Atoms
189(2)
5-10 Fischer Projections
191(5)
Summary: Fischer Projections and Their Use
196(1)
5-11 Diastereomers
196(2)
Summary: Types of Isomers
197(1)
5-12 Stereochemistry of Molecules with Two or More Asymmetric Carbons
198(1)
5-13 Meso Compounds
199(2)
5-14 Absolute and Relative Configuration
201(2)
5-15 Physical Properties of Diastereomers
203(1)
5-16 Resolution of Enantiomers
204(3)
Chapter 5 Glossary
207(2)
Study Problems
209(3)
6 Alkyl Halides: Nucleophilic Substitution and Elimination212(67)
6-1 Introduction
212(1)
6-2 Nomenclature of Alkyl Halides
213(2)
6-3 Common Uses of Alkyl Halides
215(2)
6-4 Structure of Alkyl Halides
217(1)
6-5 Physical Properties of Alkyl Halides
218(2)
6-6 Preparation of Alkyl Halides
220(5)
Summary: Methods for Preparing Alkyl Halides
223(2)
6-7 Reactions of Alkyl Halides: Substitution and Elimination
225(1)
6-8 Second-Order Nucleophilic Substitution: The SN2 Reaction
226(2)
Key Mechanism: The SN2 Reaction
227(1)
6-9 Generality of the SN2 Reaction
228(2)
Summary: SN2 Reactions of Alkyl Halides
228(2)
6-10 Factors Affecting SN2 Reactions: Strength of the Nucleophile
230(4)
Summary: Trends in Nucleophilicity
231(3)
6-11 Reactivity of the Substrate in SN2 Reactions
234(4)
6-12 Stereochemistry of the SN2 Reaction
238(2)
6-13 First-Order Nucleophilic Substitution: The SN1 Reaction
240(4)
Key Mechanism: The 5N1 Reaction
241(3)
6-14 Stereochemistry of the SN1 Reaction
244(2)
6-15 Rearrangements in SN I Reactions
246(3)
6-16 Comparison of SN1 and SN2 Reactions
249(3)
Summary: Nucleophilic Substitutions
251(1)
6-17 First-Order Elimination: The El Reaction
252(5)
Key Mechanism: The El Reaction
252(4)
Summary: Carbocation Reactions
256(1)
6-18 Positional Orientation of Elimination: Zaitsev's Rule
257(1)
6-19 Second-Order Elimination: The E2 Reaction
258(3)
Key Mechanism: The E2 Reaction
259(2)
6-20 Stereochemistry of the E2 Reaction
261(1)
6-21 Comparison of El and E2 Elimination Mechanisms
262(8)
Summary: Elimination Reactions
264(3)
Summary: Reactions of Alkyl Halides
267(3)
Chapter 6 Glossary
270(3)
Study Problems
273(6)
7 Structure and Synthesis of Alkenes279(42)
7-1 Introduction
279(1)
7-2 The Orbital Description of the Alkene Double Bond
280(1)
7-3 Elements of Unsaturation
281(2)
7-4 Nomenclature of Alkenes
283(2)
7-5 Nomenclature of Cis-Trans Isomers
285(3)
Summary: Rules for Naming Alkenes
287(1)
7-6 Commercial Importance of Alkenes
288(2)
7-7 Stability of Alkenes
290(6)
7-8 Physical Properties of Alkenes
296(2)
7-9 Alkene Synthesis by Elimination of Alkyl Halides
298(8)
7-10 Alkene Synthesis by Dehydration of Alcohols
306(3)
Key Mechanism: Acid-Catalyzed Dehydration of an Alcohol
307(2)
7-11 Alkene Synthesis by High-Temperature Industrial Methods
309(7)
Summary: Methods for Synthesis of Alkenes
314(2)
Chapter 7 Glossary
316(2)
Study Problems
318(3)
8 Reactions of Alkenes321(61)
8-1 Reactivity of the Carbon-Carbon Double Bond
321(1)
8-2 Electrophilic Addition to Alkenes
322(2)
Key Mechanism: Electrophilic Addition to Alkenes
322(2)
8-3 Addition of Hydrogen Halides to Alkenes
324(6)
8-4 Addition of Water: Hydration of Alkenes
330(3)
8-5 Hydration by Oxymercuration-Demercuration
333(2)
8-6 Alkoxymercuration-Demercuration
335(1)
8-7 Hydroboration of Alkenes
336(6)
8-8 Addition of Halogens to Alkenes
342(3)
8-9 Formation of Halohydrins
345(3)
8-10 Catalytic Hydrogenation of Alkenes
348(2)
8-11 Addition of Carbenes to Alkenes
350(3)
8-12 Epoxidation of Alkenes
353(2)
8-13 Acid-Catalyzed Opening of Epoxides
355(3)
8-14 Syn Hydroxylation of Alkenes
358(2)
8-15 Oxidative Cleavage of Alkenes
360(3)
8-16 Polymerization of Alkenes
363(11)
Summary: Reactions of Alkenes
370(4)
Chapter 8 Glossary
374(2)
Study Problems
376(6)
9 Alkynes382(35)
9-1 Introduction
382(1)
9-2 Nomenclature of Alkynes
383(1)
9-3 Physical Properties of Alkynes
384(1)
9-4 Commercial Importance of Alkynes
384(2)
9-5 Electronic Structure of Alkynes
386(1)
9-6 Acidity of Alkynes; Formation of Acetylide Ions
387(2)
9-7 Synthesis of Alkynes from Acetylides
389(4)
9-8 Synthesis of Alkynes by Elimination Reactions
393(3)
Summary: Syntheses of Alkynes
396(1)
9-9 Addition Reactions of Alkynes
396(10)
9-10 Oxidation of Alkynes
406(6)
Summary: Reactions of Alkynes
409(3)
Chapter 9 Glossary
412(1)
Study Problems
413(4)
10 Structure and Synthesis of Alcohols417(43)
10-1 Introduction
417(1)
10-2 Structure and Classification of Alcohols
417(2)
10-3 Nomenclature of Alcohols and Phenols
419(4)
10-4 Physical Properties of Alcohols
423(2)
10-5 Commercially Important Alcohols
425(2)
10-6 Acidity of Alcohols and Phenols
427(3)
10-7 Synthesis of Alcohols: Introduction and Review
430(2)
Summary: Previous Alcohol Syntheses
430(2)
10-8 Organometallic Reagents for Alcohol Synthesis
432(3)
10-9 Addition of Organometallic Reagents to Carbonyl Compounds
435(8)
Key Mechanism: Grignard Reactions
435(7)
Summary: Grignard Reactions
442(1)
10-10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides
443(2)
10-11 Reduction of the Carbonyl Group: Synthesis of 1° and 2° Alcohols
445(6)
Summary: Reactions of LiAlH4 and NaBH4
448(1)
Summary: Alcohol Syntheses
449(2)
10-12 Thiols (Mercaptans)
451(3)
Chapter 10 Glossary
454(1)
Study Problems
455(5)
11 Reactions of Alcohols460(48)
11-1 Oxidation States of Alcohols and Related Functional Groups
460(2)
11-2 Oxidation of Alcohols
462(3)
11-3 Additional Methods for Oxidizing Alcohols
465(2)
11-4 Biological Oxidation of Alcohols
467(2)
11-5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates
469(3)
Summary: SN2 Reactions of Tosylate Esters
471(1)
11-6 Reduction of Alcohols
472(1)
11-7 Reactions of Alcohols with Hydrohalic Acids
472(5)
11-8 Reactions of Alcohols with Phosphorus Halides
477(1)
11-9 Reactions of Alcohols with Thionyl Chloride
478(2)
11-10 Dehydration Reactions of Alcohols
480(8)
11-11 Unique Reactions of Diols
488(2)
11-12 Esterification of Alcohols
490(1)
11-13 Esters of Inorganic Acids
491(3)
11-14 Reactions of Alkoxides
494(8)
Key Mechanism: The Williamson Ether Synthesis
494(5)
Summary: Reactions of Alcohols
499(3)
Chapter 11 Glossary
502(1)
Study Problems
503(5)
12 Infrared Spectroscopy and Mass Spectrometry508(51)
12-1 Introduction
508(1)
12-2 The Electromagnetic Spectrum
509(1)
12-3 The Infrared Region
510
12-4 Molecular Vibrations 51
1(512)
12-5 1R-Active and IR-Inactive Vibrations
513(1)
12-6 Measurement of the IR Spectrum
514(3)
12-7 Infrared Spectroscopy of Hydrocarbons
517(5)
12-8 Characteristic Absorptions of Alcohols and Amines
522(1)
12-9 Characteristic Absorptions of Carbonyl Compounds
523(6)
12-10 Characteristic Absorptions of C-N Bonds
529(1)
12-11 Simplified Summary of IR Stretching Frequencies
530(2)
12-12 Reading and Interpreting IR Spectra (Solved Problems)
532(5)
12-13 Introduction to Mass Spectrometry
537(4)
12-14 Determination of the Molecular Formula by Mass Spectrometry
541(3)
12-15 Fragmentation Patterns in Mass Spectrometry
544(7)
Summary: Common Fragmentation Patterns
549(2)
Chapter 12 Glossary
551(1)
Study Problems
552(7)
13 Nuclear Magnetic Resonance Spectroscopy559(64)
13-1 Introduction
559(1)
13-2 Theory of Nuclear Magnetic Resonance
559(3)
13-3 Magnetic Shielding by Electrons
562(2)
13-4 The NMR Spectrometer
564(1)
13-5 The Chemical Shift
565(7)
13-6 The Number of Signals
572(1)
13-7 Areas of the Peaks
573(3)
13-8 Spin-Spin Splitting
576(9)
13-9 Complex Splitting
585(3)
13-10 Stereochemical Nonequivalence of Protons
588(3)
13-11 Time Dependence of NMR Spectroscopy
591(8)
Problem-Solving Strategy: Interpreting Proton NMR Spectra
594(5)
13-12 Carbon-13 NMR Spectroscopy
599(8)
13-13 Interpreting Carbon NMR Spectra
607(2)
13-14 Nuclear Magnetic Resonance Imaging
609(5)
Problem-Solving Strategy: Spectroscopy Problems
610(4)
Chapter 13 Glossary
614(2)
Study Problems
616(7)
14 Ethers, Epoxides, and Sulfides623(40)
14-1 Introduction
623(1)
14-2 Physical Properties of Ethers
623(5)
14-3 Nomenclature of Ethers
628(3)
14-4 Spectroscopy of Ethers
631(2)
14-5 The Williamson Ether Synthesis
633(1)
14-6 Synthesis of Ethers by Alkoxymercuration-Demercuration
634(1)
14-7 Industrial Synthesis: Bimolecular Dehydration of Alcohols
635(1)
Summary: Syntheses of Ethers
636(1)
14-8 Cleavage of Ethers by HBr and HI
636(3)
14-9 Autoxidation of Ethers
639(1)
Summary: Reactions of Ethers
639(1)
14-10 Sulfides (Thioethers)
640(2)
14-11 Synthesis of Epoxides
642(3)
Summary: Epoxide Syntheses
645(1)
14-12 Acid-Catalyzed Ring Opening of Epoxides
645(4)
14-13 Base-Catalyzed Ring Opening of Epoxides
649(1)
14-14 Orientation of Epoxide Ring Opening
650(2)
14-15 Reactions of Epoxides with Grignard and Organolithium Reagents
652(1)
14-16 Epoxy Resins: The Advent of Modern Glues
653(3)
Summary: Reactions of Epoxides
655(1)
Chapter 14 Glossary
656(2)
Study Problems
658(5)
15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy663(42)
15-1 Introduction
663(1)
15-2 Stabilities of Dienes
663(2)
15-3 Molecular Orbital Picture of a Conjugated System
665(4)
15-4 Allylic Cations
669(1)
15-5 1,2- and 1,4-Addition to Conjugated Dienes
670(2)
15-6 Kinetic versus Thermodynamic Control in the Addition of HBr to 1,3-Butadiene
672(2)
15-7 Allylic Radicals
674(2)
15-8 Molecular Orbitals of the Allylic System
676(2)
15-9 Electronic Configurations of the Ally! Radical, Cation, and Anion
678(1)
15-10 SN2 Displacement Reactions of Allylic Halides and Tosylates
679(1)
15-11 The Diels-Alder Reaction
680(9)
Key Mechanism: The Diels-Alder Reaction
680(9)
15-12 The Diels-Alder as an Example of a Pericyclic Reaction
689(3)
15-13 Ultraviolet Absorption Spectroscopy
692(7)
Chapter 15 Glossary
699(2)
Study Problems
701(4)
16 Aromatic Compounds705(44)
16-1 Introduction: The Discovery of Benzene
705(1)
16-2 The Structure and Properties of Benzene
705(4)
16-3 The Molecular Orbitals of Benzene
709(3)
16-4 The Molecular Orbital Picture of Cyclobutadiene
712(2)
16-5 Aromatic, Antiaromatic, and Nonaromatic Compounds
714(1)
16-6 Hackers Rule
714(2)
16-7 Molecular Orbital Derivation of Hiickel's Rule
716(1)
16-8 Aromatic Ions
717(6)
16-9 Heterocyclic Aromatic Compounds
723(4)
16-10 Polynuclear Aromatic Hydrocarbons
727(2)
16-11 Aromatic Allotropes of Carbon
729(2)
16-12 Fused Heterocyclic Compounds
731(1)
16-13 Nomenclature of Benzene Derivatives
732(2)
16-14 Physical Properties of Benzene and Its Derivatives
734(1)
16-15 Spectroscopy of Aromatic Compounds
735(3)
Chapter 16 Glossary
738(2)
Study Problems
740(9)
17 Reactions of Aromatic Compounds749(56)
17-1 Electrophilic Aromatic Substitution
749(2)
Key Mechanism: Electrophilic Aromatic Substitution
750(1)
17-2 Halogenation of Benzene
751(2)
17-3 Nitration of Benzene
753(2)
17-4 Sulfonation of Benzene
755(2)
17-5 Nitration of Toluene: The Effect of Alkyl Substitution
757(2)
17-6 Activating, Ortho, Para-Directing Substituents
759(4)
Summary: Activating, Ortho, Para-Directors
762(1)
17-7 Deactivating, Meta-Directing Substituents
763(3)
Summary: Deactivating, Meta-Directors
766(1)
17-8 Halogen Substituents: Deactivating, but Ortho, Para-Directing
766(2)
Summary: Directing Effects of Substituents
768(1)
17-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution
768(3)
17-10 The Friedel-Crafts Alkylation
771(4)
17-11 The Friedel-Crafts Acylation
775(5)
Summary: Comparison of Friedel-Crafts Alkylation and Acylation
778(2)
17-12 Nucleophilic Aromatic Substitution
780(5)
17-13 Addition Reactions of Benzene Derivatives
785(2)
17-14 Side-Chain Reactions of Benzene Derivatives
787(4)
17-15 Reactions of Phenols
791(6)
Summary: Reactions of Aromatic Compounds
794(3)
Chapter 17 Glossary
797(3)
Study Problems
800(5)
18 Ketones and Aldehydes805(65)
18-1 Carbonyl Compounds
805(1)
18-2 Structure of the Carbonyl Group
806(1)
18-3 Nomenclature of Ketones and Aldehydes
806(3)
18-4 Physical Properties of Ketones and Aldehydes
809(2)
18-5 Spectroscopy of Ketones and Aldehydes
811(7)
18-6 Industrial Importance of Ketones and Aldehydes
818(1)
18-7 Review of Syntheses of Ketones and Aldehydes
818(4)
18-8 Synthesis of Ketones and Aldehydes Using 1,3-Dithianes
822(1)
18-9 Synthesis of Ketones from Carboxylic Acids
823(1)
18-10 Synthesis of Ketones from Nitriles
824(1)
18-11 Synthesis of Aldehydes and Ketones from Acid Chlorides
825(4)
Summary: Syntheses of Ketones and Aldehydes
826(3)
18-12 Reactions of Ketones and Aldehydes: Nucleophilic Addition
829(3)
Key Mechanism: Nucleophilic Additions to Carbonyl Groups
831(1)
18-13 The Wittig Reaction
832(4)
18-14 Hydration of Ketones and Aldehydes
836(2)
18-15 Formation of Cyanohydrins
838(2)
18-16 Formation of Imines
840(3)
Key Mechanism: Formation of Imines
840(3)
18-17 Condensations with Hydroxylamine and Hydrazines
843(2)
Summary: Condensations of Amines with Ketones and Aldehydes
844(1)
18-18 Formation of Acetals
845(5)
Key Mechanism: Formation of Acetals
846(2)
Problem-Solving Strategy: Proposing Reaction Mechanisms
848(2)
18-19 Use of Acetals as Protecting Groups
850(2)
18-20 Oxidation of Aldehydes
852(1)
18-21 Reductions of Ketones and Aldehydes
853(5)
Summary: Reactions of Ketones and Aldehydes
855(3)
Glossary
858(3)
Study Problems
861(9)
19 Amines870(65)
19-1 Introduction
870(1)
19-2 Nomenclature of Amines
871(2)
19-3 Structure of Amines
873(2)
19-4 Physical Properties of Amines
875(2)
19-5 Basicity of Amines
877(1)
19-6 Effects on Amine Basicity
878(2)
19-7 Salts of Amines
880(2)
19-8 Amine Salts as Phase-Transfer Catalysts
882(2)
19-9 Spectroscopy of Amines
884(4)
19-10 Reactions of Amines with Ketones and Aldehydes (Review)
888(1)
19-11 Aromatic Substitution of Arylamines and Pyridine (Review)
888(4)
19-12 Alkylation of Amines by Alkyl Halides
892(1)
19-13 Acylation of Amines by Acid Chlorides
893(2)
19-14 Formation of Sulfonamides
895(2)
19-15 Amines as Leaving Groups: The Hofmann Elimination
897(3)
19-16 Oxidation of Amines: The Cope Elimination
900(2)
19-17 Reactions of Amines with Nitrous Acid
902(2)
19-18 Reactions of Arenediazonium Salts
904(7)
Summary: Reactions of Amines
908(3)
19-19 Synthesis of Amines by Reductive Amination
911(2)
19-20 Synthesis of Amines by Acylation-Reduction
913(2)
19-21 Syntheses Limited to Primary Amines
915(8)
Summary: Synthesis of Amines
921(2)
Chapter 19 Glossary
923(3)
Study Problems
926(9)
20 Carboxylic Acids935(43)
20-1 Introduction
935(1)
20-2 Nomenclature of Carboxylic Acids
935(4)
20-3 Structure and Physical Properties of Carboxylic Acids
939(1)
20-4 Acidity of Carboxylic Acids
940(4)
20-5 Salts of Carboxylic Acids
944(3)
20-6 Commercial Sources of Carboxylic Acids
947(1)
20-7 Spectroscopy of Carboxylic Acids
948(4)
20-8 Synthesis of Carboxylic Acids
952(5)
Summary: Syntheses of Carboxylic Acids
955(2)
20-9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution
957(1)
20-10 Condensation of Acids with Alcohols: The Fischer Esterification
958(4)
Key Mechanism: Fischer Esterification
959(3)
20-11 Esterification Using Diazomethane
962(1)
20-12 Condensation of Acids with Amines: Direct Synthesis of Amides
963(1)
20-13 Reduction of Carboxylic Acids
963(2)
20-14 Alkylation of Carboxylic Acids to Form Ketones
965(1)
20-15 Synthesis and Use of Acid Chlorides
966(4)
Summary: Reactions of Carboxylic Acids
968(2)
Chapter 20 Glossary
970(1)
Study Problems
971(7)
21 Carboxylic Acid Derivatives978(63)
21-1 Introduction
978(1)
21-2 Structure and Nomenclature of Acid Derivatives
979(6)
21-3 Physical Properties of Carboxylic Acid Derivatives
985(3)
21-4 Spectroscopy of Carboxylic Acid Derivatives
988(6)
21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
994(9)
Key Mechanism: Addition-Elimination Mechanism of Nucleophilic Acyl Substitution
995(8)
21-6 Transesterification
1003(3)
21-7 Hydrolysis of Carboxylic Acid Derivatives
1006(5)
21-8 Reduction of Acid Derivatives
1011(2)
21-9 Reactions of Acid Derivatives with Organometallic Reagents
1013(1)
21-10 Summary of the Chemistry of Acid Chlorides
1014(2)
21-11 Summary of the Chemistry of Anhydrides
1016(3)
21-12 Summary of the Chemistry of Esters
1019(3)
21-13 Summary of the Chemistry of Amides
1022(3)
21-14 Summary of the Chemistry of Nitriles
1025(1)
21-15 Thioesters
1026(2)
21-16 Esters and Amides of Carbonic Acid
1028(2)
Chapter 21 Glossary
1030(2)
Study Problems
1032(9)
22 Condensations and Alpha Substitutions of Carbonyl Compounds1041(56)
22-1 Introduction
1041(1)
22-2 Enols and Enolate Ions
1042(4)
22-3 Alpha Halogenation of Ketones
1046(5)
22-4 a Bromination of Acids: The HVZ Reaction
1051(1)
22-5 Alkylation of Enolate Ions
1052(1)
22-6 Formation and Alkylation of Enamines
1053(3)
22-7 The Aldol Condensation of Ketones and Aldehydes
1056(4)
Key Mechanism: Base-Catalyzed Aldol Condensation
1056(4)
22-8 Dehydration of Aldol Products
1060(1)
Key Mechanism: Base-Catalyzed Dehydration of an Aldol
1060(1)
22-9 Crossed Aldol Condensations
1061(3)
Problem-Solving Strategy: Proposing Reaction Mechanisms
1062(2)
22-10 Aldol Cyclizations
1064(1)
22-11 Planning Syntheses Using Aldol Condensations
1065(2)
22-12 The Claisen Ester Condensation
1067(3)
Key Mechanism: The Claisen Ester Condensation
1067(3)
22-13 The Dieckmann Condensation: A Claisen Cyclization
1070(1)
22-14 Crossed Claisen Condensations
1071(3)
22-15 Syntheses Using /3-Dicarbonyl Compounds
1074(2)
22-16 The Malonic Ester Synthesis
1076(3)
22-17 The Acetoacetic Ester Synthesis
1079(2)
22-18 Conjugate Additions: The Michael Reaction
1081(4)
22-19 The Robinson Annulation
1085(3)
Problem-Solving Strategy: Proposing Reaction
Mechanisms
1086(2)
Summary: Enolate Additions and Condensations
1088(2)
Chapter 22 Glossary
1090(2)
Study Problems
1092(5)
23 Carbohydrates and Nucleic Acids1097(56)
23-1 Introduction
1097(1)
23-2 Classification of Carbohydrates
1098(1)
23-3 Monosaccharides
1099(3)
23-4 Erythro and Threo Diastereomers
1102(1)
23-5 Epimers
1103(1)
23-6 Cyclic Structures of Monosaccharides
1104(4)
23-7 Anomers of Monosaccharides; Mutarotation
1108(2)
23-8 Reactions of Monosaccharides: Side Reactions in Base
1110(2)
23-9 Reduction of Monosaccharides
1112(1)
23-10 Oxidation of Monosaccharides; Reducing Sugars
1113(2)
23-11 Nonreducing Sugars: Formation of Glycosides
1115(2)
23-12 Ether and Ester Formation
1117(2)
23-13 Reactions with Phenylhydrazine: Osazone Formation
1119(1)
23-14 Chain Shortening: The Ruff Degradation
1120(1)
23-15 Chain Lengthening: The Kiliani-Fischer Synthesis
1121(3)
Summary: Reactions of Sugars
1122(2)
23-16 Fischer's Proof of the Configuration of Glucose
1124(3)
23-17 Determination of Ring Size; Periodic Acid Cleavage of Sugars
1127(2)
23-18 Disaccharides
1129(5)
23-19 Polysaccharides
1134(3)
23-20 Nucleic Acids: Introduction
1137(2)
23-21 Ribonucleosides and Ribonucleotides
1139(2)
23-22 The Structure of Ribonucleic Acid
1141(1)
23-23 Deoxyribose and the Structure of Deoxyribonucleic Acid
1141(4)
23-24 Additional Functions of Nucleotides
1145(2)
Chapter 23 Glossary
1147(2)
Study Problems
1149(4)
24 Amino Acids, Peptides, and Proteins1153(47)
24-1 Introduction
1153(1)
24-2 Structure and Stereochemistry of the a-Amino Acids
1154(4)
24-3 Acid-Base Properties of Amino Acids
1158(2)
24-4 Isoelectric Points and Electrophoresis
1160(1)
24-5 Synthesis of Amino Acids
1161(6)
Summary: Syntheses of Amino Acids
1166(1)
24-6 Resolution of Amino Acids
1167(1)
24-7 Reactions of Amino Acids
1167(3)
Summary: Reactions of Amino Acids
1170(1)
24-8 Structure and Nomenclature of Peptides and Proteins
1170(4)
24-9 Peptide Structure Determination
1174(6)
24-10 Solution-Phase Peptide Synthesis
1180(3)
24-11 Solid-Phase Peptide Synthesis
1183(5)
24-12 Classification of Proteins
1188(1)
24-13 Levels of Protein Structure
1189(2)
24-14 Protein Denaturation
1191(2)
Chapter 24 Glossary
1193(3)
Study Problems
1196(4)
25 Lipids1200(22)
25-1 Introduction
1200(1)
25-2 Waxes
1200(1)
25-3 Triglycerides
1201(3)
25-4 Saponification of Fats and Oils; Soaps and Detergents
1204(4)
25-5 Phospholipids
1208(1)
25-6 Steroids
1209(3)
25-7 Prostaglandins
1212(1)
25-8 Terpenes
1213(4)
Chapter 25 Glossary
1217(1)
Study Problems
1218(4)
26 Synthetic Polymers1222(21)
26-1 Introduction
1222(1)
26-2 Addition Polymers
1223(6)
26-3 Stereochemistry of Polymers
1229(1)
26-4 Stereochemical Control of Polymerization; Ziegler-Natta Catalysts
1230(1)
26-5 Natural and Synthetic Rubbers
1230(2)
26-6 Copolymers of Two or More Monomers
1232(1)
26-7 Condensation Polymers
1232(4)
26-8 Polymer Structure and Properties
1236(2)
Chapter 26 Glossary
1238(2)
Study Problems
1240(3)
Appendices1243
1A NMR Absorption Positions of Protons in Various Structural Environments
1244(2)
1B Spin-Spin Coupling Constants
1246(1)
1C 13C Chemical Shifts in Organic Compounds
1247(1)
2A Characteristic Infrared Group Frequencies
1248(3)
2B IR: Characteristic Infrared Absorptions of Functional Groups
1251(2)
3 UV: The Woodward-Fieser Rules for Predicting UV-Visible Spectra
1253(4)
4A Methods and Suggestions for Proposing Mechanisms
1257(3)
4B Suggestions for Developing Multistep Syntheses
1260(1)
5 pKa Values for Representative Compounds
1261
Answers to Selected ProblemsA1
Photo CreditsPC1
Indexl1

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