Chapter 1: Introduction 1.1. A Brief History of Organic Chemistry 1.2. The Variety and Beauty of Organic Molecules Chapter 2: Why Is an Acid-Base Theme Important? 2.1. Traditional Acid and Base Theory 2.2.
There are Two Acid-Base Definitions: How Are They Related? 2.3. Acid-Base Equilibria and Equilibrium Constants 2.4. Electronegativity and Atom Size 2.4.A. Electronegativity 2.
4. B. Atom Size 2.5. Atom Size and Electronegativity Arguments Applied to Acids and Bases 2.6. Resonance, Electron Dispersion and Base Strength 2.7.
Lewis Acids and Bases 2.8. Why Is Acid-Base Chemistry a Theme for Organic Chemistry? 2.9. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 3: Bonding 3.1. Atomic orbitals and Electrons 3.1.
A. Atomic Orbitals 3.1.B. Electronic Configuration 3.2. Ionic versus Covalent Chemical Bonds 3.3.
Covalent Bonds 3.4. Linear Combination of Atomic Orbital (LCAO) Model 3.5. Tetrahedral Carbons and sp3 Hybridization 3.5.A. The Experimentally Determined Structure of Methane 3.
5.B. Electron Promotion and sp3 Hybridization 3.5.C. The Hybrid Carbon Model of sp3-Hybrid Orbitals 3.6. The Valence Shell Electron Pair Repulsion (VSEPR) Model 3.
7. Breaking Covalent Bonds 3.8. Carbon Bonded to Heteroatoms 3.8.A. A Covalent Bond Between Carbon and a Heteroatom: Bond Polarization 3.8.
B. Bond Polarity, Bond Moments, and Bond Strength Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 4: Alkanes, Isomers, and an Introduction to Nomenclature 4.1. Alkanes 4.2. Structural Variations of Alkane Hydrocarbons 4.2.A.
Straight-chain and Branched Alkanes 4.2.B. Isomers 4.3. The IUPAC Rules of Nomenclature 4.3.A.
Prefixes and Simple Alkanes 4.3.B. Common Names 4.3.C. Halogens are Substituents 4.3.
D. Multiple Substituents 4.3.E. Complex Substituents 4.4. Rings Made of Carbon: Cyclic Compounds 4.5.
The Acid or Base Properties of Alkanes 4.6. Combustion Analysis and Empirical Formulas 4.7. Commercial and Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 5: Functional Groups 5.1. -Bonds. The C=C Unit and Alkenes 5.
2. -Bonds. The CºC Unit and Alkynes 5.3. Hydrocarbons With Several -Bonds 5.4. Terpenes 5.5.
Heteroatom Functional Groups 5.5.A. Alcohols and Thiols 5.5.B. Ethers and Dithioethers (Sulfides) 5.5.
C. Amines 5.6. Functional Groups With Polarized -Bonds 5.6.A. The Carbonyl Functional Group, C=O 5.6.
B. Ketones and Aldehydes 5.6.C. Carboxylic Acids, Carboxylic Anions and Resonance 5.6.D. Double and Triple Bonds to Nitrogen 5.
7. Acid-Base Properties of Functional Groups 5.8. Physical Properties and Intermolecular Forces 5.8.A. Boiling Point 5.8.
B. Solubility 5.8.C. Melting Point 5.9. Benzene: A Special Cyclic Hydrocarbon 5.10.
Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 6: Acids, Bases, and Nucleophiles 6.1. Acid-Base Equilibria 6.2. Carboxylic Acids and Sulfonic Acids 6.2.A. Carboxylic Acids 6.
2.B Sulfonic Acids 6.3. Factors That Influence the Strength of a Carboxylic Acid 6.3.A. Stability of the Conjugate Base 6.3.
B. Inductive Effects 6.3.C. Solvent Effects 6.4. Alcohols Are Amphoteric 6.5.
Amines 6.6. Carbon Acids 6.6.A. Terminal Alkynes Are Weak Acids 6.6.B.
-Hydrogen Atoms and Carbonyls 6.7. Organic Bases 6.7.A. Amines 6.7.B.
Alcohols Are Bases 6.7.C. Ethers Are Bases 6.7.D. Carbonyl Compounds Are Bases 6.7.
E. Alkenes and Alkynes Are Bases 6.8. Lewis Acids and Bases 6.9. Nucleophiles 6.10. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 7.
Chemical Reactions, Bond Energy, and Kinetics 7.1. A Chemical Reaction 7.2. Reactive Intermediates 7.2.A. Carbocations (Carbenium ions) 7.
2.B. Carbanions 7.2.C. Radicals 7.3 Formal Charge 7.4.
Free Energy: Enthalpy and Entropy 7.5. Bond Dissociation Enthalpy and Reactions 7.6. Transition States 7.7. Competing Reactions 7.8.
Reversible Chemical Reactions 7.9. Reaction Curves and Intermediates 7.10. Mechanisms 7.11. Kinetics 7.11.
A. Reaction Rate and First-Order Reactions 7.11.B. Second-Order Reactions 7.11.C. Half Life 7.
11.D. No Reaction 7.12. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 8: Conformations 8.1. Rotation Around C--C Bonds 8.1.
A. Staggered and Eclipsed Rotamers 8.1.B. Torsional Strain: Steric Hindrance and Energy Barriers 8.2. Longer Chain Alkanes 8.3.
Influence of Heteroatoms on the Rotamer Population 8.3.A. Halogen Substituents 8.3.B. OH or NH Groups in Alcohols or Amines 8.4.
Introducing -Bonds 8.5. Cyclic Alkanes 8.5.A. Strain and Steric Hindrance in Cyclic Alkanes 8.5.B.
Conformations of C3-C5 Cycloalkanes 8.5.C. Conformationally Mobile Cyclohexane 8.6. Substituted Cyclohexanes. A1,3-Strain 8.7.
Large Rings 8.8 Cyclic Alkenes 8.9. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 9: Stereoisomers: Chirality, Enantiomers, and Diastereomers 9.1. Stereogenic Carbons and Stereoisomers 9.2. Absolute Configuration [(R) and (S) Nomenclature] 9.
3. Specific Rotation: A Physical Property 9.4. Circular Dichroism 9.5. Diastereomers 9.6. Alkenes 9.
7. Cis and Trans Substituents Attached to Rings 9.8. Stereogenic Centers in Cyclic Molecules 9.9. Stereogenic Centers in Bicyclic Molecules 9.10. Optical Resolution 9.
11. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 10: Acid-Base Reactions of -Bonds: Addition Reactions 10.1. Carbocation Stability 10.2. Alkenes React With Brønsted-Lowry Acids 10.3. Carbocation Rearrangements 10.
4. Hydration Reactions of Alkenes 10.5. Alkenes React With Dihalogens 10.5.A Dihalogenation 10.5.B.
Diastereoselectivity in the Dihalogenation Reaction of Alkenes 10.5.C. Reaction With Aqueous Solutions of Halogens (Hypohalous Acids) 10.6. Alkenes React With Borane 10.7. Alkenes React With Mercury(II) Compounds 10.
8. Alkynes React as Bases 10.8.A. Reaction With Brønsted-Lowry Acids 10.8.B. Hydration of Alkynes 10.
8.C. Dihalogenation of Alkynes 10.8.D. Hydroboration of Alkynes 10.8.E.
Oxymercuration of Alkynes 10.9. Metathesis 10.10. Non-Ionic Reactions: Radical Reactions 10.11. Polymerization 10.12.
Organization of Reaction Types 10.13. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 11: Substitution Reactions 11.1. Alkyl Halides, Sulfonate Esters, and the Electrophilic C--X Bond 11.2. The SN2 Reaction 11.2.
A. Nucleophilic Approach to an Electrophilic Carbon 11.2.B. Reaction Rate and Energy Requirements 11.2.C. The Role of the Solvent 11.
3. Functional Group Transformations Via the SN2 Reaction 11.4. The SN1 Reaction 11.5. Substitution Reactions of Alcohols 11.5.A.
Alcohols React With Mineral Acids 11.5.B. Sulfur and Phosphorous Halide Reagents 11.5.C. Mitsunobu Reaction 11.6.
Reactions of Ethers 11.6.A. Ethers React as Brønsted-Lowry Bases 11.6.B. Reactions of Epoxides 11.7.
Free Radical Halogenation of Alkanes 11.8. C--H Substitution 11.9. Organization of Reaction Types 11.10. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 12: Elimination and p-Bond-Forming Reactions 12.1.
Bimolecular Elimination 12.2. Stereochemical Consequences of the E2 Reaction 12.3. The E2 Reaction in Cyclic Molecules 12.4. Unimolecular Elimination: The E1 Reaction 12.5.
Intramolecular Elimination 12.6. Elimination Reactions of Vinyl Halides: Formation of Alkynes 12.7. Substitution versus Elimination 12.8. Strength and Limitations of the Simplifying Assumptions 12.9.
Organization of Reaction Types 12.10. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK 13: Spectroscopic Methods of Identification 13.1. Light and Energy 13.2. Mass Spectrometry 13.3.
Infrared Spectroscopy 13.3.A. Absorbing Infrared Light and the Infrared Spectrophotometer 13.3.B. The Infrared Spectrum and Functional Group Absorptions 13.4.
Nuclear Magnetic Resonance Spectroscopy 13.4.A. The Nuclear Magnetic Resonance Experiment 13.4.B. The Proton NMR Spectrum 13.5.
Identifying Monofunctional Molecules 13.6. Carbon-13 NMR Spectroscopy: Counting the Carbons 13.7. Two-Dimensional (2D)-NMR 13.8.