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016610024

This document is the table of contents for the textbook "Organic Chemistry" by Stanley H. Pine. The textbook is divided into 27 chapters covering topics in organic chemistry including bonding, functional groups, reactions, stereochemistry, synthesis, and natural products. It also includes an appendix on spectroscopic methods for structure determination.

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Saleh Breakerboy
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280 views8 pages

016610024

This document is the table of contents for the textbook "Organic Chemistry" by Stanley H. Pine. The textbook is divided into 27 chapters covering topics in organic chemistry including bonding, functional groups, reactions, stereochemistry, synthesis, and natural products. It also includes an appendix on spectroscopic methods for structure determination.

Uploaded by

Saleh Breakerboy
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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ORGANIC

CHEMISTRY
Fifth Edition
Stanley H. Pine
Professor of Chemistry
California State University,

Los Angeles

McGraw-Hill, Inc.
New York St. Louis San Francisco Auckland Bogota
Caracas Lisbon London Madrid Mexico Milan
Montreal New Delhi Paris San Juan Singapore
Sydney Tokyo Toronto

Contents
1 What is Organic Chemistry?
1-1
1-2
1-3

The Chemistry of Carbon Compounds


A Historical Perspective
3
Contemporary Organic Chemistry
6

2 Bonding in Organic Molecules


2-1
2-2
2-3
2-4
2-5
2-6
2-7
2-8
2-9
2-10

Bonding
9
Structural Formulas of Organic Molecules
Electronegativity and Dipoles
22
Quantum Mechanics and Atomic Orbitals
Molecular Orbitals and Bonding
30
Hybrid Orbitals
33
Bond Angles
36
Bond Energies and Distances
41
Summary
45
Supplementary Problems
46

12
26

3 Classes and Nomenclature of Organic Compounds


Functional Groups
48
3-1
3-2
3-3

Hydrocarbons
49
Heteroatom Functional Groups
Supplementary Problems
89

65

ix

Contents

4 Characteristic Reactions of Organic Compounds


4-1
4-2
4-3
4-4
4-5

Acids and Bases


94
Reactions of Organic Compounds
Oxidation and Reduction
110
Summary
113
Supplementary Problems
113

5 Reaction Mechanism
5-1
5-2
5-3
5-4
5-5

105

116

The Reaction Mechanism


Reaction Energetics
122
Reaction Kinetics
127
Summary
129
Supplementary Problems

117

130

6 The Shapes of MoleculesStereochemistry


6-1
6-2
6-3
6-4
6-5
6-6
6-7

Representations of Three-Dimensional Molecules


Conformations of Acyclic Compounds
137
Conformations of Cyclic Compounds
140
Geometrical Isomerism
152
Chirality and Optical Activity
163
Summary
177
Supplementary Problems
178

7 Structural Effects on ReactivityResonance


7-1
7-2
7-3
7-4
7-5
7-6

93

Structural Effects on Acidity and Basicity


The Resonance Method
190
Aromatic Compounds
195
Some Consequences of Resonance
198
Summary
208
Supplementary Problems
209

132
133

182

183

8 Nucleophilic Additions to the Carbonyl Group


Aldehydes a n d Ketones
212
8-1
8-2
8-3

Reactivity of the Carbonyl Group


213
Cyanide as the NucleophileThe Cyanohydrin Reaction
219
Oxygen or Sulfur as the NucleophileAcetals, Ketals and Hydrates
223

Contents
8-4
8-5
8-6
8-7
8-8
8-9

Hydride as the NucleopheReduction


231
Carbon as the NucleopheOrganometallic Compounds
Nitrogen as the Nucleophe
248
Nucleophilic Addition to Carbonyl Analogs
253
Summary
255
Supplementary Problems
259

xi

239

9 Nucleophilic Substitutions on the Carbonyl GroupThe


Carboxylic Acid Family
265
9-1
9-2
9-3
9-4
9-5
9-6
9-7
9-8
9-9
9-10

Reactivity in the Carboxylic Acid Family


267
Oxygen or Sulfur as the NucleopheEsters and Carboxylic Acids
270
Nitrogen as the NucleopheAmides
283
Acyl Halides and Anhydrides
286
Hydride as the NucleopheReduction
291
Carbon as the NucleopheOrganometallic Reagents
295
Enantiomer Resolution
301
Nucleophilic Substitution on Derivatives of Sulfuric and Phosphoric
Acids
302
Summary
308
Supplementary Problems
312

10 Nucleophilic Substitutions at Saturated Carbon


10-1
10-2
10-3
10-4
10-5

The Reaction Mechanism


317
Stereochemistry of Nucleophilic Substitution
322
The Variables in Nucleophilic Substitution
327
Summary
343
Supplementary Problems
345

11 The Scope of Nucleophilic Substitution


11-1
11-2
11-3
11-4
11-5
11-6
11-7
11-8
11-9

316

348

NucleopheSubstrate Combinations
349
Halide as the NucleopheHaloalkanes
351
Competing Reactions
356
Oxygen and Sulfur as the NucleophilesAlcohols, Ethers, and
Sulfides
359
Nitrogen and Phosphorus as the NucleophilesAmines
372
Neighboring Group Participation
379
Hydride, Nitrile, and Organometallic Nucleophiles
383
Summary
389
Supplementary Problems
391

Contents

12 The Alpha CarbanionNucleophilic-Electrophilic


Reactivity of Carbonyl Compounds
398
12-1
12-2
12-3
12-4
12-5
12-6
12-7
12-8

Enols and Enolate Anions


399
Addition-DehydrationThe Aldol Reaction
404
Ester Condensation
411
Fragmentation of Beta-Dicarbonyl Compounds
418
Alkylation of Enolate Anions
421
Other Stabilized Carbanions and Carbon Nucleophiles
Summary
433
Supplementary Problems
435

430

13 Nucleophilic Additions and Substitutions in Synthesis


444
13-1
13-2
13-3
13-4
13-5
13-6

Available Reactions
445
Experimental Considerations
446
The Strategy of Synthesis
448
Synthesis Examples
452
Summary
456
Supplementary Problems
457

14 Elimination ReactionsAlkenes and Alkynes


14-1
14-2
14-3
14-4
14-5
14-6
14-7
14-8
14-9

The Reaction Mechanism


466
Elimination Versus Substitution
471
The Direction of Elimination
475
Stereochemistry
479
Formation of Alkenes
486
Formation of Alkynes
499
Other Double and Triple Bonds
501
Summary
506
Supplementary Problems
509

15 Electrophilic Additions to Unsaturated Carbon


15-1
15-2
15-3
15-4
15-5
15-6

464

The Mechanism of Electrophilic Addition


Direction and Stereochemistry of Addition
Additions to Alkenes and Alkynes
525
Transition Metal Organometallics
557
Summary
565
Supplementary Problems
569

519
522

517

Contents

16 Additions to Conjugated Compounds

xi

576

16-1 Conjugated Dienes


577
16-2 Double Bonds Conjugated with Carbonyl Groups
16-3 Pericyclic Reactions
588
16-4 Summary
603
16-5 Supplementary Problems
604

582

17 The Mechanism of Electrophilic Aromatic Substitution


609
17-1
17-2
17-3
17-4
17-5

Characteristics of Cyclic Polyenes


610
Mechanism and Orientation in Electrophilic Aromatic Substitution
616
Quantitative Correlations of Substituent Effects
629
Summary
635
Supplementary Problems
636

18 The Scope oi Aromatic Substitutions

638

18-1

Electrophilic Aromatic Substitution ReactionsHeteroatoms as the


Electrophiles
639
18-2 Electrophilic Aromatic Substitution ReactionsCarbon Electrophiles
650
18-3 Nucleophilic Aromatic Substitutions
662
18-4 Synthesis with Aromatic Compounds
673
18-5 Summary
682
18-6 Supplementary Problems
686

19 Polycyclic and Heterocyclic Aromatic Compounds


19-1
19-2
19-3
19-4

Polycyclic Aromatic Compounds


694
Heterocyclic Aromatic Compounds
703
Summary
715
Supplementary Problems
716

20 Organic Synthesis
20-1
20-2
20-3

721

Design of a Synthesis
722
Reaction Patterns
728
Stereochemistry
741

693

Xiv

Contents
20-4
20-5
20-6

Applications and Examples


Summary
753
Supplementary Problems

744
753

21 Carbohydrates a n d Nucleosides
21-1
21-2
21-3
21-4
21-5
21-6
21-7

Characteristics and Properties of Carbohydrates


Chemistry of Monosaccharides
764
Oligosaccharides and Polysaccharides
786
Nucleosides and Nucleotides
796
Sunlight, Carbohydrates, and Energy
800
Summary
805
Supplementary Problems
807

22 mino Acids a n d Proteins


22-1
22-2
22-3
22-4
22-5

858

Glycerol Derivatives
859
Terpenes
866
Steroids
875
Prostaglandins
885
Pheromones
894
Summary
900
Supplementary Problems
901

24 Free Radicals
24-1
24-2
24-3
24-4
24-5
24-6

811

Amino Acids
812
Peptides
822
Proteins, Enzymes, and Biosynthesis
Summary
854
Supplementary Problems
855

23 Lipids
23-1
23-2
23-3
23-4
23-5
23-6
23-7

757

909

History
911
Characteristics of Free Radicals
912
Reactions
922
Detection of Free Radicals
937
Summary
939
Supplementary Problems
940

840

758

Contents

25 Natural a n d Synthetic Polymers


25-1
25-2
25-3
25-4
25-5

Structural Characteristics
945
Preparation of Synthetic Polymers
Fibers
963
Summary
969
Supplementary Problems
970

26 Molecular Rearrangements
26-1
26-2
26-3
26-4
26-5

944
951

972

Rearrangement to an Electron-Deficient Atom


973
Free-Radical and Anionic Rearrangements
995
Orbital Symmetry Considerations
1000
Summary
1014
Supplementary Problems
1015

27 Photochemistry a n d Electrochemistry
27-1
27-2
27-3
27-4
27-5
27-6

Principles of Photochemistry
1023
Photochemical Reactions
1028
Principles of Electrochemistry
1042
Electrochemical Reactions
1046
Summary
1057
Supplementary Problems
1057

APPENDIX: Spectroscopic Methods


A-l
A-2
A-3
A-4
A-5
A-6
A-7

1021

1062

Electromagnetic Radiation
1064
Nuclear Magnetic Resonance Spectroscopy
1065
Infrared Spectroscopy
1095
Ultraviolet and Visible Spectroscopy
1113
Mass Spectrometry
1120
Spectroscopic Solution of Structural Problems
1132
Supplementary Problems
1139

Index

1157

XV

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