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Introduction
1.1. (Very) Brief Refresher of the Basics
1.2. The Octet Rule
1.3. Basics of Bonding
1.4. VSEPR Theory
1.5. Hybrid Orbitals
1.6. Lewis Structures
1.7. Hashed and Wedged Notation
1.8. Other Representations of Molecules
Chapter 1 Learning Outcomes
Chapter 1 Practice Problems
Chapter 1 Practice Problems - Answers
Chapter 1 References
2.1. Why Do We Care?
2.2. Functional Groups
2.3. Types of Intermolecular Forces
2.4. Effects of Intermolecular Forces
2.5. Nomenclature
Chapter 2 Learning Outcomes
Chapter 2 Practice Problems
Chapter 2 Practice Problems - Answers
3.1. Rotations Around Single (σ) Bonds
3.2. Newman Projections
3.3. Dihedral/Torsion Angles
3.4. Types of Strain in Molecules
3.5. Naming Conformations from Rotations Around a σ Bond
3.6. Strain and Conformation in Cyclic Molecules
Chapter 3 Learning Outcomes
Chapter 3 Practice Problems
Chapter 3 Practice Problems - Answers
4.1. Preamble – Stereochemistry and Other Textbooks
4.2. Classification of Isomers
4.3. Unusual Cases of Chirality and Stereogenicity
4.4. Stereoisomerism From Pi (π) Bonds
4.5. Adding Stereochemical Information to IUPAC Names
4.6. Physical Properties of Enantiomers vs. Diastereomers
4.7. Optical Rotation
Chapter 4 Learning Outcomes
Chapter 4 Practice Problems
Chapter 4 Practice Problems - Answers
Chapter 4 References
5.1. Reaction Equations vs. Reaction Mechanisms
5.2. Over-the-Arrow Notation in Chemical Reactions
5.3. Drawing Reaction Mechanisms
5.4. Reaction Coordinates
5.5. Resonance
Chapter 5 Learning Outcomes
Chapter 5 Practice Problems
Chapter 5 Practice Problems - Answers
Chapter 5 References
6.1. (Very) Brief Refresher of the Basics
6.2. Reaction Coordinates of Acid-Base Reactions
6.3. Qualitative Estimates of Acidity
6.4. Quantitative Acidity
Chapter 6 Learning Outcomes
Chapter 6 Practice Problems
Chapter 6 Practice Problems - Answers
7.1. (Very) Brief Refresher of the Basics
7.2. Terminology: Nucleophiles and Electrophiles
7.3. Simple Nucleophilic Attacks on Carbonyls
7.4. Oxidation States
7.5. Catalysis of Addition Reactions
7.6. Additions of Organometallics to Pi (π) Bonds
7.7. Leaving Groups
7.8. Stereochemistry of Addition Reactions
Chapter 7 Learning Outcomes
Chapter 7 Practice Problems
Chapter 7 Practice Problems - Answers
8.1. (Very) Brief Refresher of the Basics
8.2. General Form of the Reaction
8.3. Regioselectivity
8.4. Stereoselectivity
8.5. Reaction: Addition of H-X
8.6. Reaction: Addition of H-OH
8.7. Reaction: Addition of X-X
8.8. Reaction: Addition of X-OH or X-OR
8.9. Reaction: Epoxidation
8.10. Reaction: Addition of HO-OH or HO-OR
8.11. Reaction: Addition of H-H
Chapter 8 Learning Outcomes
Chapter 8 Practice Problems
Chapter 8 Practice Problems - Answers
9.1. (Very) Brief Discussion on the Uses of Molecular Orbital Theory with Aromaticity
9.2. Aromaticity
9.3. Practical Considerations – Achieving Aromaticity and Avoiding Anti-Aromaticity
9.4. How to Classify Compounds as Aromatic, Anti-Aromatic, and Non-Aromatic
9.5. Nomenclature
Chapter 9 Learning Outcomes
Chapter 9 Practice Problems
Chapter 9 Practice Problems - Answers
10.1. (Very) Brief Refresher of the Basics
10.2. Terminology: Electrophilic Aromatic Substitution (EAS) // SEAr
10.3. General Form and Mechanism
10.4. Reaction Coordinate and Rate-Determining Step
10.5. Reaction: Halogenation
10.6. Reaction: Nitration
10.7. Reaction: Sulfonation
10.8. Reaction: Alkylation via Friedel-Crafts
10.9. Reaction: Acylation via Friedel-Crafts
10.10. Regioselectivity and Substituent Effects
Chapter 10 Learning Outcomes
Chapter 10 Practice Problems
Chapter 10 Practice Problems - Answers
11.1. (Very) Brief Refresher of the Basics
11.2. Substitution Reactions: SN2 Reactions
11.3. Substitution Reactions: SN1 Reactions
11.4. How to Determine if a Reaction Follows an SN2 or SN1 Mechanism
11.5. Solving Problems Using Special Nucleophiles
Chapter 11 Learning Outcomes
Chapter 11 Practice Problems
Chapter 11 Practice Problems - Answers
12.1. Addition vs. Elimination, SN2 and SN1 vs. E2 and E1
12.2. Elimination Reactions: E2 Reactions
12.3. Elimination Reactions: E1 Reactions
12.4. Determining if a Reaction Follows an E2 or E1 Mechanism
12.5. Reaction: Elimination of H-OH (Dehydration)
12.6. Reaction: Elimination of H-X (Dehydrohalogenation)
12.7. Oxidation of Alcohols via Elimination
Chapter 12 Learning Outcomes
Chapter 12 Practice Problems
Chapter 12 Practice Problems - Answers
13.1. (Very) Brief Refresher of the Basics
13.2. Concept and General Form
13.3. Mechanism, Reaction Coordinate, and Rate-Determining Step
13.4. Reaction Rates and Relative Reactivity
13.5. Reactions with Acid Halide Electrophiles
13.6. Reactions with Anhydride Electrophiles
13.7. Reactions with Carboxylic Acid/Ester Electrophiles
13.8. Reductions of Acyl Compounds Using Hydrides
13.9. Multiple Additions of Organometallic Reagents to Acyl Compounds
Chapter 13 Learning Outcomes
Chapter 13 Practice Problems
Chapter 13 Practice Problems - Answers
Acknowledgements
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Introduction to Organic Chemistry by Steven Langdon is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.