ORGANIC CHEMISTRY, Ninth Edition, is revised to align with the way students approach complicated material. It includes pull-out organic chemistry reaction roadmaps organized by chapter to help you devise your own reaction pathways. Emphasizing practical “how-to” skills, the new edition is packed with problems, along with hundreds of detailed solutions to all in-chapter exercises to guide you through logical approaches to solving problems. New point-by-point summaries at the beginning of each section highlight important content in a way that is easy to review and reference, while in-margin definitions and highlighted integral concepts reinforce key content throughout the text. In the eBook and OWLv2 course, there are 100 author-created videos that explain and illustrate the most difficult concepts.
Author(s): William Brown, Eric Anslyn, Christopher Foote, Brent Iverson
Edition: 9
Publisher: Cengage Learning
Year: 2022
Language: English
Pages: 1377
City: Boston
Cover
Dedication
About the Authors
Contents in Brief
Contents
List of Mechanisms
Careers in Chemistry
Preface
Acknowledgments
Chapter 1: Covalent Bonding and Shapes of Molecules
1.1 Electronic Structure of Atoms
1.2 Lewis Model of Bonding
1.3 Functional Groups
1.4 Bond Angles and Shapes of Molecules
1.5 Polar and Nonpolar Molecules
1.6 Quantum or Wave Mechanics
1.7 A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding
1.8 Resonance
1.9 Molecular Orbitals for Delocalized Systems
1.10 Bond Lengths and Bond Strengths in Alkanes, Alkenes, and Alkynes
Problems
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
2.4 Cycloalkanes
2.5 Conformations of Alkanes and Cycloalkanes
2.6 Cis, Trans Isomerism in Cycloalkanes and Bicycloalkanes
2.7 Physical Properties of Alkanes and Cycloalkanes
2.8 Reactions of Alkanes
2.9 Sources and Importance of Alkanes
Problems
Chapter 3: Stereoisomerism and Chirality
3.1 Chirality - The Handedness of Molecules
3.2 Stereoisomerism
3.3 Naming Chiral Centers - The R,S System
3.4 Acyclic Molecules with Two or More Stereocenters
3.5 Cyclic Molecules with Two or More Chiral Centers
3.6 Tying All the Terminology Together
3.7 Optical Activity - How Chirality Is Detected in the Laboratory
3.8 The Significance of Chirality in the Biological World
3.9 Separation of Enantiomers - Resolution
Problems
Chapter 4: Acids and Bases
4.1 Arrhenius Acids and Bases
4.2 Bronsted-Lowry Acids and Bases
4.3 Acid Dissociation Constants, pKa, and the Relative Strengths of Acids and Bases
4.4 The Position of Equilibriumin Acid-Base Reactions
4.5 Thermochemistry and Mechanisms of Acid-Base Reactions
4.6 Molecular Structure and Acidity
4.7 Lewis Acids and Bases
Problems
Chapter 5: Alkenes: Bonding, Nomenclature, and Properties
5.1 Structure of Alkenes
5.2 Nomenclature of Alkenes
5.3 Physical Properties of Alkenes
5.4 Naturally Occurring Alkenes - Terpene Hydrocarbons
Problems
Chapter 6: Reactions of Alkenes
6.1 Reactions of Alkenes - An Overview
6.2 Organic Reactions Involving Reactive Intermediates
6.3 Terminology
6.4 Electrophilic Additions
6.5 Hydroboration-Oxidation
6.6 Oxidation
6.7 Reduction
6.8 Molecules Containing Chiral Centers as Reactants or Products
Problems
Chapter 7: Alkynes
7.1 Structure of Alkynes
7.2 Nomenclature of Alkynes
7.3 Physical Properties of Alkynes
7.4 Acidity of 1-Alkynes
7.5 Preparation of Alkynes
7.6 Reaction Mechanisms
7.7 Electrophilic Addition to Alkynes
7.8 Hydration of Alkynes to Aldehydes and Ketones
7.9 Reduction of Alkynes
7.10 Organic Synthesis
Problems
Chapter 8: Haloalkanes, Halogenation, and Radical Reactions
8.1 Structure
8.2 Nomenclature
8.3 Physical Properties of Haloalkanes
8.4 Preparation of Haloalkanes by Halogenation of Alkanes
8.5 Mechanism of Halogenation of Alkanes
8.6 Allylic Halogenation
8.7 Radical Autoxidation
8.8 Radical Addition of HBr to Alkenes
Problems
Chapter 9: Nucleophilic Substitution and B-Elimination
9.1 Nucleophilic Substitution in Haloalkanes
9.2 Mechanisms of Nucleophilic Aliphatic Substitution
9.3 Experimental Evidence for SN1 and SN2 Mechanisms
9.4 Analysis of Several Nucleophilic Substitution Reactions
9.5 B-Elimination
9.6 Mechanisms of B-Elimination
9.7 Experimental Evidence for E1 and E2 Mechanisms
9.8 Substitution versus Elimination
9.9 Analysis of Several Competitions between Substitutions and Eliminations
9.10 Neighboring Group Participation
Problems
Chapter 10: Alcohols
10.1 Structure and Nomenclature of Alcohols
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
10.6 Acid-Catalyzed Dehydration of Alcohols
10.7 The Pinacol Rearrangement
10.8 Oxidation of Alcohols
10.9 Thiols
Problems
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
11.5 Reactions of Ethers
11.6 Silyl Ethers as Protecting Groups
11.7 Epoxides: Structure and Nomenclature
11.8 Synthesis of Epoxides
11.9 Reactions of Epoxides
11.10 Ethylene Oxide and Epichlorohydrin: Building Blocks in Organic Synthesis
11.11 Crown Ethers
11.12 Sulfides
Problems
Chapter 12: Infrared Spectroscopy
12.1 Electromagnetic Radiation
12.2 Molecular Spectroscopy
12.3 Infrared Spectroscopy
12.4 Interpreting Infrared Spectra
12.5 Solving Infrared Spectral Problems
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
13.8 Signal Splitting and the (n + 1) Rule
13.9 The Origins of Signal Splitting
13.10 Stereochemistry and Topicity
13.11 13C-NMR
13.12 Interpretation of NMR Spectra
Problems
Chapter 14: Mass Spectrometry
14.1 A Mass Spectrometer
14.2 Features of a Mass Spectrum
14.3 Interpreting Mass Spectra
14.4 Mass Spectrometry in the Organic Synthesis Laboratory and Other Applications
Problems
Chapter 15: An Introduction to Organometallic Compounds
15.1 Organomagnesium and Organolithium Compounds
15.2 Lithium Diorganocopper (Gilman) Reagents
15.3 Carbenes and Carbenoids
Problems
Chapter 16: Aldehydes and Ketones
16.1 Structure and Bonding
16.2 Nomenclature
16.3 Physical Properties
16.4 Reactions
16.5 Addition of Carbon Nucleophiles
16.6 The Wittig Reaction
16.7 Addition of Oxygen Nucleophiles
16.8 Addition of Nitrogen Nucleophiles
16.9 Keto-Enol Tautomerism
16.10 Oxidation
16.11 Reduction
16.12 Reactions at an a-Carbon
Problems
Chapter 17: Carboxylic Acids
17.1 Structure
17.2 Nomenclature
17.3 Physical Properties
17.4 Acidity
17.5 Preparation of Carboxylic Acids
17.6 Reduction
17.7 Esterification
17.8 Conversion to Acid Chlorides
17.9 Decarboxylation
Problems
Chapter 18: Functional Derivatives of Carboxylic Acids
18.1 Structure and Nomenclature
18.2 Acidity of Amides, Imides, and Sulfonamides
18.3 Characteristic Reactions
18.4 Carboxylic Acid Derivative Reaction Mechanisms
18.5 Reaction with Water: Hydrolysis
18.6 Reaction with Alcohols
18.7 Reactions with Ammonia and Amines
18.8 Reaction of Acid Chlorides with Salts of Carboxylic Acids
18.9 Interconversion of Functional Derivatives
18.10 Reactions with Organometallic Compounds
18.11 Reduction
Problems
Chapter 19: Enolate Anions and Enamines
19.1 Formation and Reactions of Enolate Anions: An Overview
19.2 Aldol Reaction
19.3 Claisen and Dieckmann Condensations
19.4 Claisen and Aldol Condensations in the Biological World
19.5 Enamines
19.6 Acetoacetic Ester Synthesis
19.7 Malonic Ester Synthesis
19.8 Conjugate Addition to a,B-Unsaturated Carbonyl Compounds
19.9 Crossed Enolate Reactions Using LDA
Problems
Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions
20.1 Stability of Conjugated Dienes
20.2 Electrophilic Addition to Conjugated Dienes
20.3 UV-Visible Spectroscopy
20.4 Pericyclic Reaction Theory
20.5 The Diels-Alder Reaction
20.6 Sigmatropic Shifts
Problems
Chapter 21: Benzene and the Concept of Aromaticity
21.1 The Structure of Benzene
21.2 The Concept of Aromaticity
21.3 Nomenclature
21.4 Phenols
21.5 Reactions at a Benzylic Position
Problems
Chapter 22: Reactions of Benzene and Its Derivatives
22.1 Electrophilic Aromatic Substitution
22.2 Disubstitution and Polysubstitution
22.3 Nucleophilic Aromatic Substitution
Problems
Chapter 23: Amines
23.1 Structure and Classification
23.2 Nomenclature
23.3 Chirality of Amines and Quaternary Ammonium Ions
23.4 Physical Properties
23.5 Basicity
23.6 Reactions with Acids
23.7 Preparation
23.8 Reaction with Nitrous Acid
23.9 Hofmann Elimination
23.10 Cope Elimination
Problems
Chapter 24: Catalytic Carbon-Carbon Bond Formation
24.1 Carbon-Carbon Bond-Forming Reactions from Earlier Chapters
24.2 Organometallic Compounds and Catalysis
24.3 The Heck Reaction
24.4 Catalytic Allylic Alkylation
24.5 Palladium-Catalyzed Cross-Coupling Reactions
24.6 Alkene Metathesis
24.7 Click Chemistry
Problems
Chapter 25: Carbohydrates
25.1 Monosaccharides
25.2 The Cyclic Structure of Monosaccharides
25.3 Reactions of Monosaccharides
25.4 Disaccharides and Oligosaccharides
25.5 Polysaccharides
25.6 Glucosaminoglycans
Problems
Chapter 26: Organic Polymer Chemistry
26.1 The Architecture of Polymers
26.2 Polymer Notation and Nomenclature
26.3 Molecular Weights of Polymers
26.4 Polymer Morphology - Crystalline versus Amorphous Materials
26.5 Step-Growth Polymerizations
26.6 Chain-Growth Polymerizations
Problems
Appendix 1: Thermodynamics and the Equilibrium Constant
Appendix 2: Major Classes of Organic Acids
Appendix 3: Bond Dissociation Enthalpies
Appendix 4: Characteristic 1H-NMR Chemical Shifts
Appendix 5: Characteristic 13C-NMR Chemical Shifts
Appendix 6: Characteristic Infrared Absorption Frequencies
Appendix 7: Electrostatic Potential Maps
Appendix 8: Summary of Stereochemical Terms
Appendix 9: Summary of the Rules of Nomenclature
Glossary
Index
Appendix 10: Organic Chemistry Reaction Roadmaps
