Organic Chemistry 8th Edition by William H Brown, Brent L Iverson, Eric Anslyn, Christopher S Foote ISBN 1305580354 9781305580350

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ISBN 10: 1305580354
ISBN 13: 9781305580350
Author: William H Brown, Brent L Iverson, Eric Anslyn, Christopher S Foote

Organic Chemistry 8th Edition Table of contents:

Chapter 1. Covalent Bonding and Shapes of Molecules

1.1. Electronic Structure of Atoms

A. Electron Configuration of Atoms

B. The Concept of Energy

C. Lewis Dot Structures

1.2. Lewis Model of Bonding

A. Formation of Chemical Bonds

B. Electronegativity and Chemical Bonds

C. Lewis Structures for Molecules and Polyatomic Ions

D. Formal Charge

E. Exceptions to the Octet Rule

F. Dative Bonds

1.3. Functional Groups

A. Alcohols

B. Amines

C. Aldehydes and Ketones

D. Carboxylic Acids

E. Carboxylic Esters

F. Carboxylic Amides

1.4. Bond Angles and Shapes of Molecules

1.5. Polar and Nonpolar Molecules

1.6. Quantum or Wave Mechanics

A. Moving Particles Exhibit the Properties of a Wave

B. Shapes of Atomic s and p Orbitals

1.7. A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding

A. Molecular Orbital Theory; Formation of Molecular Orbitals

B. Valence Bond Theory; Hybridization of Atomic Orbitals

C. An Analysis of S and P

D. Combining Valence Bond (VB) and Molecular Orbital (MO) Theories: The Creation of σ and π Bonding and Antibonding Orbitals

1.8. Resonance

A. Theory of Resonance

B. Rules for Writing Acceptable Contributing Structures

C. Estimating the Relative Importance of Contributing Structures

1.9. Molecular Orbitals for Delocalized Systems

A. Resonance Revisited

B. A Greater Reliance on Molecular Orbital Theory

C. Hybridization Considerations in Light of Resonance and MO Theory

1.10. Bond Lengths and Bond Strengths in Alkanes, Alkenes, and Alkynes

Study Guide

Problems

Electronic Structure of Atoms

Lewis Structures and Formal Charge

Polarity of Covalent Bonds

Bond Angles and Shapes of Molecules

Functional Groups

Polar and Nonpolar Molecules

Resonance and Contributing Structures

Valence Bond Theory

Combined MO/VB Theory

Additional Problems

Looking Ahead

Molecular Orbitals

I. Things You Should Know: General Conclusions from Quantum Mechanics

Predicting Structure and Bonding

Predicting Structure and Bonding

Predicting Stability and Properties

Predicting Reactions

Chapter 2. Alkanes and Cycloalkanes

2.1. The Structure of Alkanes

2.2. Constitutional Isomerism in Alkanes

2.3. Nomenclature of Alkanes and the IUPAC System

A. The IUPAC System

B. Common Names

C. The IUPAC System—A General System of Nomenclature

D. Classification of Carbon and Hydrogen Atoms

2.4. Cycloalkanes

A. Structure and Nomenclature

B. Bicycloalkanes

2.5. Conformations of Alkanes and Cycloalkanes

A. Alkanes

B. Cycloalkanes

2.6. Cis,Trans Isomerism in Cycloalkanes and Bicycloalkanes

A. Cis,Trans Isomerism in Cycloalkanes

B. Cis,Trans Isomerism in Bicycloalkanes

2.7. Physical Properties of Alkanes and Cycloalkanes

A. Dispersion Forces and Interactions among Alkane Molecules

B. Boiling Points, Melting Points, and Density

C. Constitutional Isomers Have Different Physical Properties

2.8. Reactions of Alkanes

A. Oxidation

B. Heats of Combustion and Relative Stability of Alkanes and Cycloalkanes

2.9. Sources and Importance of Alkanes

A. Natural Gas

B. Petroleum

C. Coal

Study Guide

Problems

Constitutional Isomerism

Nomenclature of Alkanes and Cycloalkanes

Conformations of Alkanes and Cycloalkanes

Cis,Trans Isomerism in Cycloalkanes

Physical Properties

Reactions of Alkanes

Looking Ahead

Chapter 3. Stereoisomerism and Chirality

3.1. Chirality—The Handedness of Molecules

3.2. Stereoisomerism

3.3. Naming Chiral Centers—The R , S System

A. Priority Rules

3.4. Acyclic Molecules with Two or More Stereocenters

A. Enantiomers and Diastereomers

B. Meso Compounds

C. Fischer Projection Formulas

3.5. Cyclic Molecules with Two or More Chiral Centers

A. Disubstituted Derivatives of Cyclopentane

B. Disubstituted Derivatives of Cyclohexane

3.6. Tying All the Terminology Together

3.7. Optical Activity—How Chirality Is Detected in the Laboratory

A. Plane-Polarized Light

B. Polarimeters

C. Racemic Mixtures

D. Achiral Molecules

E. Optical Purity (Enantiomeric Excess)

3.8. The Significance of Chirality in the Biological World

A. Chirality in Enzymes

B. How an Enzyme Distinguishes between a Molecule and Its Enantiomer

3.9. Separation of Enantiomers—Resolution

A. Resolution by means of Diastereomeric Salts

B. Enzymes as Resolving Agents

C. Resolution by means of Chromatography on a Chiral Substrate

Study Guide

Problems

Chirality

Enantiomers

Designation of Configuration—The R , S System

Molecules with Two or More Chiral Centers

Looking Ahead

Chapter 4. Acids and Bases

4.1. Arrhenius Acids and Bases

4.2. Brønsted-Lowry Acids and Bases

A. Conjugate Acid-Base Pairs Differ by a Proton

B. Brønsted-Lowry Bases with Two or More Receptor Sites

C. π Electrons as Brønsted-Lowry Bases

4.3. Acid Dissociation Constants, p K a , and the Relative Strengths of Acids and Bases

4.4. The Position of Equilibrium in Acid-Base Reactions

4.5. Thermochemistry and Mechanisms of Acid-Base Reactions

A. Thermal Reactions and Transition States

B. Reaction Coordinate Diagrams and Thermochemistry

C. Mechanism and Thermochemistry of Acid-Base Reactions

4.6. Molecular Structure and Acidity

A. Electronegativity of the Atom Bearing the Negative Charge

B. Size of the Atom Bearing the Negative Charge

C. Delocalization of Charge in the Anion

D. Inductive Effect and Electrostatic Stabilization of the Anion

E. Hybridization and the Percent s Character of the Atom Bearing the Negative Charge

4.7. Lewis Acids and Bases

Study Guide

Problems

Quantitative Measure of Acid and Base Strength

Thermodynamics, Kinetics, and Reaction Coordinate Diagrams

Position of Equilibrium in Acid-Base Reactions

Lewis Acids and Bases

Additional Problems

Looking Ahead

Chapter 5. Alkenes: Bonding, Nomenclature, and Properties

5.1. Structure of Alkenes

A. Shapes of Alkenes

B. Carbon-Carbon Double Bond Orbitals

C. Cis,Trans Isomerism in Alkenes

5.2. Nomenclature of Alkenes

A. IUPAC Names

B. Common Names

C. Systems for Designating Configuration in Alkenes

D. Cycloalkenes

E. Cis,Trans Isomerism in Cycloalkenes

F. Bridgehead Alkenes

G. Dienes, Trienes, and Polyenes

H. Cis,Trans Isomerism in Dienes, Trienes, and Polyenes

5.3. Physical Properties of Alkenes

5.4. Naturally Occurring Alkenes—Terpene Hydrocarbons

Study Guide

Problems

Structure of Alkenes

Nomenclature of Alkenes

Molecular Modeling

Terpenes

Looking Ahead

II. Things You Should Know: Nucleophiles and Electrophiles

Nucleophiles and Electrophiles: A Comparison to Lewis and Brønsted-Lowry Definitions

III. Things You Should Know: Reaction Mechanisms

Developing a Reaction Mechanism A.

A. Developing a Reaction Mechanism

B. The Correct Use of Arrows to Indicate Electron Movement

C. Electron Sources and Sinks: How to Predict What Will Occur in an Organic Reaction Mechanism

D. Putting it All Together: A Multiple-Choice Situation

Chapter 6. Reactions of Alkenes

6.1. Reactions of Alkenes—An Overview

6.2. Organic Reactions Involving Reactive Intermediates

A. Reaction Coordinate Diagrams

B. Thermodynamics of Addition Reactions

6.3. Electrophilic Additions

A. Addition of Hydrogen Halides

B. Addition of Water: Acid-Catalyzed Hydration

C. Carbocation Rearrangements

D. Addition of Bromine and Chlorine

E. Addition of HOCl and HOBr

F. Oxymercuration-Reduction

6.4. Hydroboration-Oxidation

6.5. Oxidation

A. Os ‍ O 4 —Oxidation of an Alkene to a Glycol

B. Ozone—Cleavage of a Carbon-Carbon Double Bond (Ozonolysis)

6.6. Reduction

A. Mechanism of Catalytic Reduction

B. Heats of Hydrogenation and the Relative Stabilities of Alkenes

6.7. Molecules Containing Chiral Centers as Reactants or Products

A. Reaction of Achiral Starting Materials in an Achiral Environment

B. Reaction of a Chiral Starting Material in an Achiral Environment

C. Reaction of Achiral Starting Materials in a Chiral Environment

Study Guide

Problems

Energetics of Chemical Reactions

Electrophilic Additions

Hydroboration

Oxidation

Reduction

Synthesis

Reactions That Produce Chiral Compounds

Looking Ahead

Organic Chemistry Reaction Roadmap

Chapter 7. Alkynes

7.1. Structure of Alkynes

7.2. Nomenclature of Alkynes

A. IUPAC Names

B. Common Names

7.3. Physical Properties of Alkynes

7.4. Acidity of 1-Alkynes

7.5. Preparation of Alkynes

A. Alkylation of Acetylide Anions with Methyl and 1 ° Haloalkanes

B. Alkynes from Alkenes

7.6. Electrophilic Addition to Alkynes

A. Addition of Bromine and Chlorine

B. Addition of Hydrogen Halides

7.7. Hydration of Alkynes to Aldehydes and Ketones

A. Hydroboration-Oxidation

B. Acid-Catalyzed Hydration

7.8. Reduction of Alkynes

A. Catalytic Reduction

B. Hydroboration-Protonolysis

C. Dissolving-Metal Reduction

7.9. Organic Synthesis

A. Retrosynthetic Analysis

B. Reactions of Functional Groups in Complex Molecules

Study Guide

Problems

Preparation of Alkynes

Reactions of Alkynes

Syntheses

Looking Ahead

Organic Chemistry Reaction Roadmap

Multistep Synthesis

Reactions in Context

Chapter 8. Haloalkanes, Halogenation, and Radical Reactions

8.1. Structure

8.2. Nomenclature

A. IUPAC System

B. Common Names

8.3. Physical Properties of Haloalkanes

A. Polarity

B. Boiling Point

C. Density

D. Bond Lengths and Bond Strengths

8.4. Preparation of Haloalkanes by Halogenation of Alkanes

A. Regioselectivity

B. Energetics

8.5. Mechanism of Halogenation of Alkanes

A. Formation of Radicals

B. A Radical Chain Mechanism

C. Energetics of Chain Propagation Steps

D. Regioselectivity of Bromination versus Chlorination: Hammond’s Postulate

E. Stereochemistry of Radical Halogenation

8.6. Allylic Halogenation

A. Mechanism of Allylic Halogenation

B. Structure of the Allyl Radical

8.7. Radical Autoxidation

8.8. Radical Addition of HBr to Alkenes

Study Guide

Problems

Nomenclature

Physical Properties

Halogenation of Alkanes

Allylic Halogenation

Organic Chemistry Reaction Roadmap

Synthesis

Autoxidation

Looking Ahead

IV. Things You Should Know: Common Mistakes in Arrow Pushing

Backward Arrows

Backward Arrows

Not Enough Arrows

Hypervalency

Mixed Media Errors

Failing to Conserve Charge

Chapter 9. Nucleophilic Substitution and β -Elimination

9.1. Nucleophilic Substitution in Haloalkanes

9.2. Mechanisms of Nucleophilic Aliphatic Substitution

A. S N 2 Mechanism

B. S N 1 Mechanism

C. Key Mechanistic Differences between S N 2 and S N 1 Reactions

9.3. Experimental Evidence for S N 1 and S N 2 Mechanisms

A. Kinetics and Stereochemistry

B. Structure of the Alkyl Portion of the Haloalkane

C. The Leaving Group

D. The Solvent

E. Structure of the Nucleophile

F. Skeletal Rearrangement

9.4. Analysis of Several Nucleophilic Substitution Reactions

9.5. β -Elimination

9.6. Mechanisms of β -Elimination

A. E1 Mechanism

B. E2 Mechanism

9.7. Experimental Evidence for E1 and E2 Mechanisms

A. Kinetics

B. Regioselectivity

C. Stereoselectivity

9.8. Substitution versus Elimination

A. S N 1 versus E1 Reactions

B. S N 2 versus E2 Reactions

C. Putting It All Together

9.9. Analysis of Several Competitions between Substitutions and Eliminations

9.10. Neighboring Group Participation

Study Guide

Problems

Nucleophilic Aliphatic Substitution

β -Eliminations

Substitution versus Elimination

Synthesis

Looking Ahead

Organic Chemistry Reaction Roadmap

Multistep Synthesis Problems

Reactions in Context

Chapter 10. Alcohols

10.1. Structure and Nomenclature of Alcohols

A. Structure

B. Nomenclature

10.2. Physical Properties of Alcohols

10.3. Acidity and Basicity of Alcohols

10.4. Reaction of Alcohols with Active Metals

10.5. Conversion of Alcohols to Haloalkanes and Sulfonates

A. Reaction with HCl , HBr , and HI

B. Reaction with Phosphorus Tribromide

C. Reaction with Thionyl Chloride and Thionyl Bromide

D. Formation of Aryl and Alkyl Sulfonates

10.6. Acid-Catalyzed Dehydration of Alcohols

10.7. The Pinacol Rearrangement

10.8. Oxidation of Alcohols

A. Chromic Acid

B. Pyridinium Chlorochromate

C. Swern Oxidation

D. Dess-Martin Oxidation

E. Periodic Acid Oxidation of Glycols

10.9. Thiols

A. Structure

B. Nomenclature

C. Physical Properties

D. Thiols in Biological Molecules

E. Preparation

F. Acidity

G. Oxidation

Study Guide

Problems

Structure and Nomenclature

Physical Properties of Alcohols

Acid-Base Reactions of Alcohols

Reactions of Alcohols

Pinacol Rearrangement

Synthesis

Looking Ahead

Organic Chemistry Reaction Roadmap

Mixed Synthesis

Reactions in Context

Chapter 11. Ethers, Epoxides, and Sulfides

11.1. Structure of Ethers

11.2. Nomenclature of Ethers

11.3. Physical Properties of Ethers

11.4. Preparation of Ethers

A. Williamson Ether Synthesis

B. Acid-Catalyzed Dehydration of Alcohols

C. Acid-Catalyzed Addition of Alcohols to Alkenes

11.5. Reactions of Ethers

A. Acid-Catalyzed Cleavage by Concentrated HX

B. Ether Safety Alert: Flammability and Formation of Hydroperoxides

11.6. Silyl Ethers as Protecting Groups

11.7. Epoxides: Structure and Nomenclature

11.8. Synthesis of Epoxides

A. Ethylene Oxide

B. Internal Nucleophilic Substitution in Halohydrins

C. Oxidation of Alkenes with Peroxycarboxylic Acids

D. Sharpless Asymmetric Epoxidation

11.9. Reactions of Epoxides

A. Acid-Catalyzed Ring Opening

B. Nucleophilic Ring Opening

11.10. Ethylene Oxide and Epichlorohydrin: Building Blocks in Organic Synthesis

11.11. Crown Ethers

11.12. Sulfides

A. Nomenclature

B. Preparation of Sulfides

C. Oxidation of Sulfides

Study Guide

Problems

Structure and Nomenclature

Physical Properties

Preparation of Ethers

Reactions of Ethers

Synthesis and Reactions of Epoxides

Synthesis

Looking Ahead

Organic Chemistry Reaction Roadmap

Mixed Synthesis

Reactions in Context

Chapter 12. Infrared Spectroscopy

12.1. Electromagnetic Radiation

12.2. Molecular Spectroscopy

12.3. Infrared Spectroscopy

A. The Vibrational Infrared Spectrum

B. Molecular Vibrations

C. Characteristic Absorption Patterns

D. Correlation Tables

12.4. Interpreting Infrared Spectra

A. Alkanes

B. Alkenes

C. Alkynes

D. Arenes (Benzene and Its Derivatives)

E. Alcohols

F. Ethers

G. Amines

H. Aldehydes and Ketones

I. Carboxylic Acids

J. Derivatives of Carboxylic Acids

12.5. Solving Infrared Spectral Problems

Study Guide

Problems

Chapter 13. Nuclear Magnetic Resonance Spectroscopy

13.1. Nuclear Spin States

13.2. Orientation of Nuclear Spins in an Applied Magnetic Field

13.3. Nuclear Magnetic “Resonance”

13.4. An NMR Spectrometer

13.5. Equivalent Hydrogens

13.6. Signal Areas

13.7. Chemical Shift

A. Electronegativity of nearby Atoms

B. Hybridization of Adjacent Atoms

C. Diamagnetic Effects from π Bonds

13.8. Signal Splitting and the ( n + 1 ) Rule

13.9. The Origins of Signal Splitting

A. Predicting Peak Intensities

B. Physical Basis for the ( n + 1 ) Rule

C. More Complex Splitting Patterns

D. Bond Rotation

E. Coincidental Overlap

F. Complex Coupling in Flexible Molecules

G. Fast Exchange

13.10. Stereochemistry and Topicity

13.11. C 13 -NMR

13.12. Interpretation of NMR Spectra

A. Alkanes

B. Alkenes

C. Alcohols

D. Ethers

E. Aldehydes and Ketones

F. Carboxylic Acids and Esters

G. Amines

H. Final Word

Study Guide

Problems

Interpretation of H 1 -NMR and C 13 -NMR Spectra

Chapter 14. Mass Spectrometry

14.1. A Mass Spectrometer

14.2. Features of a Mass Spectrum

A. Resolution

B. The Presence of Isotopes

C. Relative Abundance of M , M + 2 , and M + 1 Peaks

D. Fragmentation of Molecular Ions

14.3. Interpreting Mass Spectra

A. Alkanes

B. Alkenes

C. Alkynes

D. Alcohols

E. Aldehydes and Ketones

F. Carboxylic Acids, Esters, and Amides

G. Aromatic Hydrocarbons

H. Amines

14.4. Mass Spectrometry in the Organic Synthesis Laboratory and Other Applications

Study Guide

Problems

Chapter 15. An Introduction to Organometallic Compounds

15.1. Organomagnesium and Organolithium Compounds

A. Formation and Structure

B. Reaction with Proton Acids

C. Reaction with Oxiranes

15.2. Lithium Diorganocopper (Gilman) Reagents

A. Formation and Structure

B. Coupling with Organohalogen Compounds

C. Reaction with Oxiranes

15.3. Carbenes and Carbenoids

A. Methylene

B. Dichlorocarbene

C. The Simmons-Smith Reaction

Study Guide

Problems

Looking Ahead

Organic Chemistry Reaction Roadmap

Synthesis

Reactions in Context

Chapter 16. Aldehydes and Ketones

16.1. Structure and Bonding

16.2. Nomenclature

A. IUPAC Nomenclature

B. IUPAC Names for More Complex Aldehydes and Ketones

C. Common Names

16.3. Physical Properties

16.4. Reactions

16.5. Addition of Carbon Nucleophiles

A. Addition of Grignard Reagents

B. Addition of Organolithium Compounds

C. Addition of Anions of Terminal Alkynes

D. Addition of Hydrogen Cyanide

16.6. The Wittig Reaction

16.7. Addition of Oxygen Nucleophiles

A. Addition of Water: Formation of Carbonyl Hydrates

B. Addition of Alcohols: Formation of Acetals

C. Acetals as Carbonyl-Protecting Groups

D. Tetrahydropyranyl Ethers: Protecting an Alcohol as an Acetal

16.8. Addition of Nitrogen Nucleophiles

A. Ammonia and Its Derivatives

B. Hydrazine and Related Compounds

16.9. Keto-Enol Tautomerism

A. Acidity of α -Hydrogens

B. The Position of Equilibrium in Keto-Enol Tautomerism

16.10. Oxidation

A. Oxidation of Aldehydes

B. Oxidation of Ketones

16.11. Reduction

A. Metal Hydride Reductions

B. Catalytic Reduction

C. Selective Reduction

D. Reductive Amination

E. Reduction of a Carbonyl Group to a Methylene Group

16.12. Reactions at an α -Carbon

A. Racemization

B. Deuterium Exchange

C. α -Halogenation

Study Guide

Problems

Structure and Nomenclature

Addition of Carbon Nucleophiles

Wittig Reaction

Addition of Oxygen Nucleophiles

Addition of Nitrogen Nucleophiles

Keto-Enol Tautomerism

Oxidation/Reduction of Aldehydes and Ketones

Reactions at an α -Carbon

Synthesis

Looking Ahead

Organic Chemistry Reaction Roadmap

Synthesis

Reactions in Context

Chapter 17. Carboxylic Acids

17.1. Structure

17.2. Nomenclature

A. IUPAC System

B. Common Names

17.3. Physical Properties

17.4. Acidity

A. Acid Ionization Constants

B. Reaction with Bases

17.5. Preparation of Carboxylic Acids

17.6. Reduction

A. Lithium Aluminum Hydride

B. Selective Reduction of Other Functional Groups

17.7. Esterification

A. Fischer Esterification

B. Formation of Methyl Esters Using Diazomethane

17.8. Conversion to Acid Chlorides

17.9. Decarboxylation

A. β -Ketoacids

B. Malonic Acid and Substituted Malonic Acids

Study Guide

Problems

Structure and Nomenclature

Physical Properties

Preparation of Carboxylic Acids

Acidity of Carboxylic Acids

Reactions of Carboxylic Acids

Looking Ahead

Organic Chemistry Reaction Roadmap

Synthesis

Reactions in Context

V. Things You Should Know: Carboxylic Acid Derivative Reaction Mechanisms

Fischer Esterification Revisited

Fischer Esterification Revisited

Chapter 18. Functional Derivatives of Carboxylic Acids

18.1. Structure and Nomenclature

A. Acid Halides

B. Acid Anhydrides

C. Esters

D. Amides and Imides

E. Nitriles

18.2. Acidity of Amides, Imides, and Sulfonamides

18.3. Characteristic Reactions

A. Nucleophilic Acyl Addition

B. Nucleophilic Acyl Substitution

C. Relative Reactivity

D. Catalysis

18.4. Reaction with Water: Hydrolysis

A. Acid Chlorides

B. Acid Anhydrides

C. Esters

D. Amides

E. Nitriles

18.5. Reaction with Alcohols

A. Acid Halides

B. Acid Anhydrides

C. Esters

D. Amides

18.6. Reactions with Ammonia and Amines

A. Acid Halides

B. Acid Anhydrides

C. Esters

D. Amides

18.7. Reaction of Acid Chlorides with Salts of Carboxylic Acids

18.8. Interconversion of Functional Derivatives

18.9. Reactions with Organometallic Compounds

A. Grignard Reagents

B. Organolithium Compounds

C. Lithium Diorganocuprates

18.10. Reduction

A. Esters

B. Amides

C. Nitriles

Study Guide

Problems

Structure and Nomenclature

Physical Properties

Spectroscopy

Reactions

Synthesis

Mechanisms

Looking Ahead

Organic Chemistry Reaction Roadmap

Synthesis

Reactions in Context

Chapter 19. Enolate Anions and Enamines

19.1. Formation and Reactions of Enolate Anions: An Overview

19.2. Aldol Reaction

A. Mechanisms

B. Crossed and Intramolecular Aldol Reactions

C. Retrosynthetic Analysis

19.3. Claisen and Dieckmann Condensations

A. Claisen Condensation

B. Dieckmann Condensation

C. Crossed Claisen Condensations

D. Retrosynthetic Analysis

E. Hydrolysis and Decarboxylation of β -Ketoesters

19.4. Claisen and Aldol Condensations in the Biological World

19.5. Enamines

A. Alkylation of Enamines

B. Acylation of Enamines

C. Retrosynthetic Analysis

19.6. Acetoacetic Ester Synthesis

A. Five Sequential Reactions

B. Retrosynthetic Analysis

C. Variants

19.7. Malonic Ester Synthesis

A. Five Sequential Reactions

B. Retrosynthetic Analysis

19.8. Conjugate Addition to α , β -Unsaturated Carbonyl Compounds

A. Michael Addition of Enolate Anions

B. Retrosynthetic Analysis

C. Robinson Annulation

D. Retrosynthetic Analysis

E. Conjugate Addition of Lithium Diorganocopper Reagents

19.9. Crossed Enolate Reactions Using LDA

A. Acid-Base Considerations

B. Base Stoichiometry

C. Crossed Enolate Reactions Using LDA

D. Kinetic versus Thermodynamic Enolates

Study Guide

Problems

The Aldol Reaction

The Claisen Condensation

Enamines

Acetoacetic Ester and Malonic Ester Syntheses

Michael Reactions

Directed Aldol and Alkylation

Retrosynthetic Analysis

Synthesis

Organic Chemistry Reaction Roadmap

Multi-Step Synthesis

Reactions in Context

Chapter 20. Dienes, Conjugated Systems, and Pericyclic Reactions

20.1. Stability of Conjugated Dienes

20.2. Electrophilic Addition to Conjugated Dienes

A. 1,2-Addition and 1,4-Addition

B. Kinetic versus Thermodynamic Control of Electrophilic Addition

20.3. UV-Visible Spectroscopy

A. Introduction

B. The Origin of Transitions between Electronic Energy Levels

20.4. Pericyclic Reaction Theory

A. Frontier Molecular Orbital Theory (FMOT)

20.5. The Diels-Alder Reaction

A. Diene Must Be Able to Assume an s-Cis Conformation

B. The Effect of Substituents on Rate

C. Diels-Alder Reactions Can Be Used to Form Bicyclic Systems

D. The Configuration of the Dienophile Is Retained

E. The Configuration at the Diene Is Retained

F. Exploiting the Stereochemistry of the Diels-Alder Reaction

G. A Word of Caution about Electron Pushing

20.6. Sigmatropic Shifts

A. The Claisen Rearrangement

B. The Cope Rearrangement

C. Stereochemistry of the Cope Rearrangement

Study Guide

Problems

Structure and Stability

Electrophilic Addition to Conjugated Dienes

Ultraviolet-Visible Spectra

Frontier Molecular Orbital Theory

Diels-Alder Reaction

Sigmatropic Shifts

Organic Chemistry Reaction Roadmap

Chapter 21. Benzene and the Concept of Aromaticity

21.1. The Structure of Benzene

A. Kekulé’s Model of Benzene

B. The Molecular Orbital Model of Benzene

C. The Resonance Model of Benzene

21.2. The Concept of Aromaticity

A. The Hückel Criteria for Aromaticity

B. Aromatic Hydrocarbons

C. Antiaromatic Hydrocarbons

D. Heterocyclic Aromatic Compounds

E. Aromatic Hydrocarbon Ions

21.3. Nomenclature

A. Monosubstituted Benzenes

B. Disubstituted Benzenes

C. Polysubstituted Benzenes

21.4. Phenols

A. Structure and Nomenclature

B. Acidity of Phenols

C. Acid-Base Reactions of Phenols

D. Preparation of Alkyl-Aryl Ethers

E. Kolbe Carboxylation: Synthesis of Salicylic Acid

F. Oxidation to Quinones

21.5. Reactions at a Benzylic Position

A. Oxidation

B. Halogenation

C. Hydrogenolysis of Benzyl Ethers

Study Guide

Problems

Nomenclature and Structural Formulas

Resonance in Aromatic Compounds

The Concept of Aromaticity

Spectroscopy

Acidity of Phenols

Reactions at the Benzylic Position

Organic Chemistry Reaction Roadmap

Synthesis

Chapter 22. Reactions of Benzene and Its Derivatives

22.1. Electrophilic Aromatic Substitution

A. Chlorination and Bromination

B. Nitration and Sulfonation

C. Friedel-Crafts Alkylation and Acylation

D. Other Electrophilic Aromatic Alkylations

22.2. Disubstitution and Polysubstitution

A. Effects of a Substituent Group on Further Substitution

B. Theory of Directing Effects

C. Theory of Activating-Deactivating Effects

22.3. Nucleophilic Aromatic Substitution

A. Nucleophilic Substitution by way of a Benzyne Intermediate

B. Nucleophilic Substitution by Addition-Elimination

Study Guide

Problems

Electrophilic Aromatic Substitution: Monosubstitution

Disubstitution and Polysubstitution

Nucleophilic Aromatic Substitution

Organic Chemistry Reaction Roadmap

Syntheses

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Tags: William H Brown, Brent L Iverson, Eric Anslyn, Christopher S Foote, Organic Chemistry