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Acknowledgement
1 Why This Chapter?
1.1 Atomic Structure: The Nucleus
1.2 Atomic Structure: Orbitals
1.3 Atomic Structure: Electron Configurations
1.4 Development of Chemical Bonding Theory
1.5 Describing Chemical Bonds: Valence Bond Theory
1.6 sp3 Hybrid Orbitals and the Structure of Methane
1.7 sp3 Hybrid Orbitals and the Structure of Ethane
1.8 sp2 Hybrid Orbitals and the Structure of Ethylene
1.9 sp Hybrid Orbitals and the Structure of Acetylene
1.10 Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
1.11 Drawing Chemical Structures
1.12 Polar Covalent Bonds and Electronegativity
1.13 Polar Covalent Bonds and Dipole Moments
1.14 Formal Charges
1.15 Resonance
1.16 Rules for Resonance Forms
1.17 Acids and Bases: The Brønsted–Lowry Definition
1.18 Acid and Base Strength
1.19 Predicting Acid–Base Reactions from pKa Values
1.20 Organic Acids and Organic Bases
1.21 Acids and Bases: The Lewis Definition
1.22 Noncovalent Interactions between Molecules
Chemistry Matters — Organic Foods: Risk versus Benefit
Chemistry Matters — Alkaloids: From Cocaine to Dental Anesthetics
Key Terms
Summary
Additional Problems 1
2 Why This Chapter?
2.1 Functional Groups
2.2 Alkanes and Alkane Isomers
2.3 Alkyl Groups
2.4 Naming Alkanes
2.5 Naming Cycloalkanes
2.6 Properties of Alkanes
2.7 Conformations of Ethane
2.8 Conformations of Other Alkanes
2.9 Cis–Trans Isomerism in Cycloalkanes
2.10 Stability of Cycloalkanes: Ring Strain
2.11 Conformations of Cycloalkanes
2.12 Conformations of Cyclohexane
2.13 Axial and Equatorial Bonds in Cyclohexane
2.14 Conformations of Monosubstituted Cyclohexanes
2.15 Conformations of Disubstituted Cyclohexanes
Chemistry Matters — Gasoline
Chemistry Matters — Molecular Mechanics
Additional Problems 2
3 Why This Chapter?
3.1 Enantiomers and the Tetrahedral Carbon
3.2 The Reason for Handedness in Molecules: Chirality
3.3 Optical Activity
3.4 Pasteur’s Discovery of Enantiomers
3.5 Sequence Rules for Specifying Configuration
3.6 Diastereomers
3.7 Meso Compounds
3.8 Racemic Mixtures and the Resolution of Enantiomers
3.9 A Review of Isomerism
3.10 Chirality in Nature and Chiral Environments
Chemistry Matters — Chiral Drugs
Additional Problems 3
4 Why This Chapter?
4.1 Naming Alkenes and Alkynes
4.2 Electronic Structure of Alkenes
4.3 Cis-Trans Isomers
4.4 Alkene Stereochemistry and the E,Z Designation
4.5 Kinds of Organic Reactions
4.6 How Organic Reactions Occur: Mechanisms
4.7 An Example of a Polar Reaction: Addition of HBr to Ethylene
4.8 Describing a Reaction: Energy Diagrams and Transition States
4.9 Describing a Reaction: Intermediates and Catalysts
4.10 Using Curved Arrows in Polar Reaction Mechanisms
Chemistry Matters — Where Do Drugs Come From?
Additional Problems 4
5 Why This Chapter?
5.1 Electrophilic Addition Reactions of Alkenes: Markovnikov's Rule
5.2 Carbocation Structure and Stability
5.3 Hydration of Alkenes: Addition of H2O
5.4 Halogenation of Alkenes: Addition of X2
5.5 Reduction of Alkenes: Hydrogenation
5.6 Oxidation of Alkenes: Epoxidation and Hydroxylation
5.7 Radical Additions to Alkenes: Chain-Growth Polymers
5.8 Stability of Conjugated Dienes: Molecular Orbital Theory
5.9 Electrophilic Additions to Conjugated Dienes: Allylic Carbocations
5.10 Reactions of Alkynes: Addition of HX and X2
5.11 Hydration of Alkynes
5.12 Reduction of Alkynes
5.13 Alkyne Acidity: Formation of Acetylide Anions
5.14 Alkylation of Acetylide Anions
Chemistry Matters — Bioprospecting: Hunting for Natural Products
Chemistry Matters — The Art of Organic Synthesis
Chemistry Matters — Terpenes: Naturally Occurring Alkenes
Additional Problems 5
6 Why This Chapter?
6.1 Names and Structures of Alkyl Halides
6.2 Preparing Alkyl Halides from Alkanes: Radical Halogenation
6.3 Preparing Alkyl Halides from Alkenes
6.4 Reactions of Alkyl Halides: Grignard Reagents
6.5 Oxidation and Reduction in Organic Chemistry
Chemistry Matters — Naturally Occurring Organohalides
Additional Problems 6
7 Why This Chapter?
7.1 The Discovery of Nucleophilic Substitution Reactions
7.2 The SN2 Reaction
7.3 Characteristics of the SN2 Reaction
7.4 The SN1 Reaction
7.5 Characteristics of the SN1 Reaction
7.6 Biological Substitution Reactions
7.7 Elimination Reactions: Zaitsev’s Rule
7.8 The E2 Reaction
7.9 Biological Elimination Reactions
7.10 The E1 and E1cB Reactions
7.11 A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2
Chemistry Matters — Green Chemistry
Additional Problems 7
8 Why This Chapter?
8.1 Structure and Stability of Benzene
8.2 Naming Aromatic Compounds
8.3 Electrophilic Aromatic Substitution Reactions: Bromination
8.4 Other Aromatic Substitutions
8.5 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction
8.6 Substituent Effects in Electrophilic Substitutions
8.7 An Explanation of Substituent Effects
8.8 Oxidation and Reduction of Aromatic Compounds
8.9 Other Aromatic Compounds
Chemistry Matters — Aspirin, NSAIDs, and COX-2 Inhibitors
Additional Problems 8
9 Why This Chapter?
9.1 Naming Alcohols and Phenols
9.2 Properties of Alcohols and Phenols
9.3 Names and Properties of Ethers
9.4 Preparation of Alcohols: A Review
9.5 Alcohols from Carbonyl Compounds: Reduction
9.6 Alcohols from Carbonyl Compounds: Grignard Reaction
9.7 Reactions of Alcohols
9.8 Oxidation of Alcohols
9.9 Phenols and Their Uses
9.10 Reactions of Phenols
9.11 Preparing Ethers
9.12 Reactions of Ethers: Acidic Cleavage
9.13 Cyclic Ethers: Epoxides
9.14 Reactions of Epoxides: Ring-Opening
9.15 Thiols and Sulfides
Chemistry Matters — Ethanol: Chemical, Drug, and Poison
Chemistry Matters — Epoxy Resins and Adhesives
Key Terms and Summary of Reactions
Additional Problems 9
10 Why This Chapter?
10.1 Naming Aldehydes and Ketones
10.2 Preparing Aldehydes and Ketones
10.3 Oxidation of Aldehydes and Ketones
10.4 Nucleophilic Addition Reactions of Aldehydes and Ketones
10.5 Nucleophilic Addition of H2O: Hydration
10.6 Nucleophilic Addition of HCN: Cyanohydrin Formation
10.7 Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
10.8 Nucleophilic Addition of Amines: Imine and Enamine Formation
10.9 Nucleophilic Addition of Alcohols: Acetal Formation
10.10 Biological Reductions
Chemistry Matters — Enantioselective Synthesis
Additional Problems 10
11 Why This Chapter?
11.1 Naming Carboxylic Acids, Nitriles and Carboxylic Acid Derivatives
11.2 Occurrence and Properties of Carboxylic Acids and Derivatives
11.3 Acidity of Carboxylic Acids
11.4 Synthesis of Carboxylic Acids
11.5 Nucleophilic Acyl Substitution Reactions
11.6 Reactions of Carboxylic Acids
11.7 Chemistry of Acid Halides
11.8 Chemistry of Acid Anhydrides
11.9 Chemistry of Esters
11.10 Chemistry of Amides
11.11 Chemistry of Nitriles
11.12 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
11.13 Polyamides and Polyesters: Step-Growth Polymers
Chemistry Matters — Vitamin C
Chemistry Matters — β-Lactam Antibiotics
Additional Problems 11: Carboxylic Acids and Nitriles
Additional Problems 11: Carboxylic Acid Derivatives
12 Why This Chapter?
12.1 Naming Amines
12.2 Structure and Properties of Amines
12.3 Basicity of Amines
12.4 Synthesis of Amines
12.5 Reactions of Amines
12.6 Heterocyclic Amines
Chemistry Matters — Green Chemistry II: Ionic Liquids
Additional Problems 12
Appendix A | Nomenclature of Polyfunctional Organic Compounds
Appendix B | Acidity Constants for Some Organic Compounds
Appendix C | Glossary
Appendix D | Periodic Table
Appendix E: Bond Dissociation Energies for Some Organic Compounds
Appendix F: Infrared Absorptions of Some Adlehydes and Ketones
D • Periodic Table
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Fundamentals of Organic Chemistry-OpenStax Adaptation Copyright © by Kirsten Kramer and Cassandra Lilly is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.