Organic Chemistry: Concepts and Applications - Headley Allan D. 2020


Bonding and Structure of Organic Compounds

1.1 Introduction

1.2 Electronic Structure of Atoms

1.3 Chemical Bonds

1.4 Chemical Formulas

1.5 The Covalent Bond

1.6 Bonding — Concept Summary and Applications

1.7 Intermolecular Attractions

1.8 Intermolecular Molecular Interactions — Concept Summary and Applications

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Carbon Functional Groups and Organic Nomenclature

2.1 Introduction

2.2 Functional Groups

2.3 Saturated Hydrocarbons

2.4 Organic Nomenclature

2.5 Structure and Nomenclature of Alkanes

2.6 Unsaturated Hydrocarbons

2.7 Structure and Nomenclature of Alkenes

2.8 Structure and Nomenclature of Substituted Benzenes

2.9 Structure and Nomenclature of Alkynes

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Heteroatomic Functional Groups and Organic Nomenclature

3.1 Properties and Structure of Alcohols, Phenols, and Thiols

3.2 Nomenclature of Alcohols

3.3 Nomenclature of Thiols

3.4 Structure and Properties of Aldehydes and Ketones

3.5 Nomenclature of Aldehydes

3.6 Nomenclature of Ketones

3.7 Structure and Properties of Carboxylic Acids

3.8 Nomenclature of Carboxylic Acids

3.9 Structure and Properties of Esters

3.10 Structure and Properties of Acid Chlorides

3.11 Structure and Properties of Anhydrides

3.12 Structure and Properties of Amines

3.13 Structure and Properties of Amides

3.14 Structure and Properties of Nitriles

3.15 Structure and Properties of Ethers

3.16 An Overview of Spectroscopy and the Relationship to Functional Groups

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Alkanes, Cycloalkanes, and Alkenes: Isomers, Conformations, and Stabilities

4.1 Introduction

4.2 Structural Isomers

4.3 Conformational Isomers of Alkanes

4.4 Conformational Isomers of Cycloalkanes

4.5 Geometric Isomers

4.6 Stability of Alkanes

4.7 Stability of Alkenes

4.8 Stability of Alkynes

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5.1 Introduction

5.2 Chiral Stereoisomers

5.3 Significance of Chirality

5.4 Nomenclature of the Absolute Configuration of Chiral Molecules

5.5 Properties of Stereogenic Compounds

5.6 Compounds with More Than One Stereogenic Carbon

5.7 Resolution of Enantiomers

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An Overview of the Reactions of Organic Chemistry

6.1 Introduction

6.2 Acid—Base Reactions

6.3 Addition Reactions

6.4 Reduction Reactions

6.5 Oxidation Reactions

6.6 Elimination Reactions

6.7 Substitution Reactions

6.8 Pericyclic Reactions

6.9 Catalytic Coupling Reactions

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Acid—Base Reactions in Organic Chemistry

7.1 Introduction

7.2 Lewis Acids and Bases

7.3 Relative Strengths of Acids and Conjugate Bases

7.4 Predicting the Relative Strengths of Acids and Bases

7.5 Factors That Affect Acid and Base Strengths

7.6 Applications of Acid—Bases Reactions in Organic Chemistry

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Addition Reactions Involving Alkenes and Alkynes

8.1 Introduction

8.2 The Mechanism for Addition Reactions Involving Alkenes

8.3 Addition of Hydrogen Halide to Alkenes (Hydrohalogenation of Alkenes)

8.4 Addition of Halogens to Alkenes (Halogenation of Alkenes)

8.5 Addition of Halogens and Water to Alkenes (Halohydrin Formation)

8.6 Addition of Water to Alkenes (Hydration of Alkenes)

8.7 Addition of Carbenes to Alkenes

8.8 The Mechanism for Addition Reactions Involving Alkynes

8.9 Applications of Addition Reactions to Synthesis

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Addition Reactions Involving Carbonyls and Nitriles

9.1 Introduction

9.2 Mechanism for Addition Reactions Involving Carbonyl Compounds

9.3 Addition of HCN to Carbonyl Compounds

9.4 Addition of Water to Carbonyl Compounds

9.5 Addition of Alcohols to Carbonyl Compounds

9.6 Addition of Ylides to Carbonyl Compounds (The Wittig Reaction)

9.7 Addition of Enolates to Carbonyl Compounds

9.8 Addition of Amines to Carbonyl Compounds

9.9 Mechanism for Addition Reactions Involving Imines

9.10 Mechanism for Addition Reactions Involving Nitriles

9.11 Applications of Addition Reactions to Synthesis

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Reduction Reactions in Organic Chemistry

10.1 Introduction

10.2 Reducing Agents of Organic Chemistry

10.3 Reduction of C=O and C=S Containing Compounds

10.4 Reduction of Imines

10.5 Reduction of Oxiranes

10.6 Reduction of Aromatic Compounds, Alkynes, and Alkenes

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Oxidation Reactions in Organic Chemistry

11.1 Introduction

11.2 Oxidation

11.3 Oxidation of Alcohols and Aldehydes

11.4 Oxidation of Alkenes Without Bond Cleavage

11.5 Oxidation of Alkenes with Bond Cleavage

11.6 Applications of Oxidation Reactions of Alkenes

11.7 Oxidation of Alkynes

11.8 Oxidation of Aromatic Compounds

11.9 Autooxidation of Ethers and Alkenes

11.10 Applications of Oxidation Reactions to Synthesis

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Elimination Reactions of Organic Chemistry

12.1 Introduction

12.2 Mechanisms of Elimination Reactions

12.3 Elimination of Hydrogen and Halide (Dehydrohalogenation)

12.4 Elimination of Water (Dehydration)

12.5 Applications of Elimination Reactions to Synthesis

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Spectroscopy Revisited, A More Detailed Examination

13.1 Introduction

13.2 The Electromagnetic Spectrum

13.3 UV-Vis Spectroscopy and Conjugated Systems

13.4 Infrared Spectroscopy

13.5 Mass Spectrometry

13.6 Nuclear Magnetic Resonance (NMR) Spectroscopy

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Free Radical Substitution Reactions Involving Alkanes

14.1 Introduction

14.2 Types of Alkanes and Alkyl Halides

14.3 Chlorination of Alkanes

14.4 Bromination of Alkanes

14.5 Applications of Free Radical Substitution Reactions

14.6 Free Radical Inhibitors

14.7 Environmental Impact of Organohalides and Free Radicals

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Nucleophilic Substitution Reactions at sp3 Carbons

15.1 Introduction

15.2 The Electrophile

15.3 The Leaving Group

15.4 The Nucleophile

15.5 Nucleophilic Substitution Reactions

15.6 Bimolecular Substitution Reaction Mechanism (SN2 Mechanism)

Unimolecular Substitution Reaction Mechanism (SN1 Mechanism)

15.8 Applications of Nucleophilic Substitution Reactions — Synthesis

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Nucleophilic Substitution Reactions at Acyl Carbons

16.1 Introduction

16.2 Mechanism for Acyl Substitution

16.3 Substitution Reactions Involving Acid Chlorides

16.4 Substitution Reactions Involving Anhydrides

16.5 Substitution Reactions Involving Esters

16.6 Substitution Reactions Involving Amides

16.7 Substitution Reactions Involving Carboxylic Acids

16.8 Substitution Reactions Involving Oxalyl Chloride

16.9 Substitution Reactions Involving Sulfur Containing Compounds

16.10 Applications of Acyl Substitution Reactions

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Aromaticity and Aromatic Substitution Reactions

17.1 Introduction

17.2 Structure and Properties of Benzene

17.3 Nomenclature of Substituted Benzene

17.4 Stability of Benzene

17.5 Characteristics of Aromatic Compounds

17.6 Electrophilic Aromatic Substitution Reactions of Benzene

17.7 Electrophilic Aromatic Substitution Reactions of Substituted Benzene

17.8 Applications — Synthesis of Substituted Benzene Compounds

17.9 Electrophilic Substitution Reactions of Polycyclic Aromatic Compounds

17.10 Electrophilic Substitution Reactions of Pyrrole

17.11 Electrophilic Substitution Reactions of Pyridine

17.12 Nucleophilic Aromatic Substitution

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Conjugated Systems and Pericyclic Reactions

18.1 Conjugated Systems

18.2 Pericyclic Reactions

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Catalytic Carbon—Carbon Coupling Reactions

19.1 Introduction

19.2 Reactions of Transition Metal Complexes

19.3 Palladium-Catalyzed Coupling Reactions

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Synthetic Polymers and Biopolymers

20.1 Introduction

20.2 Cationic Polymerization of Alkenes

20.3 Anionic Polymerization of Alkenes

20.4 Free Radical Polymerization of Alkenes

20.5 Copolymerization of Alkenes

20.6 Properties of Polymers

20.7 Biopolymers

20.8 Amino Acids, Monomers of Peptides and Proteins

20.9 Acid—Base Properties of Amino Acids

20.10 Synthesis of α-Amino Acids

20.11 Reactions of α-Amino Acids

20.12 Primary Structure and Properties of Peptides

20.13 Secondary Structure of Proteins

20.14 Monosaccharides, Monomers of Carbohydrates

20.15 Reactions of Monosaccharides

20.16 Disaccharides and Polysaccharides

20.17 N-Glycosides and Amino Sugars

20.18 Lipids

20.19 Properties and Reactions of Waxes

20.20 Properties and Reactions of Triglycerides

20.21 Properties and Reactions of Phospholipids

20.22 Structure and Properties of Steroids, Prostaglandins, and Terpenes

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