Contents

1. Introduction

2. Acknowledgements

3. Chapter 1: Basic Concepts in Chemical Bonding and Organic Molecules

   1. 1.1 Chemical Bonding

   2. 1.2 Lewis Structure

   3. 1.3 Resonance Structures

   4. 1.4 Resonance Structures in Organic Chemistry

   5. 1.5 Valence-Shell Electron-Pair Repulsion Theory (VSEPR)

   6. 1.6 Valence Bond Theory and Hybridization

   7. Answers to Chapter 1 Practice Questions

4. Chapter 2: Fundamentals of Organic Structures

   1. 2.1 Structures of Alkenes

   2. 2.2 Nomenclature of Alkanes

   3. 2.3 Functional Groups

   4. 2.4 IUPAC Naming of Organic Compounds with Functional Groups

   5. 2.5 Degree of Unsaturation/Index of Hydrogen Deficiency

   6. 2.6 Intermolecular Force and Physical Properties of Organic Compounds

   7. Answers to Chapter 2 Practice Questions

5. Chapter 3: Acids and Bases: Introduction to Organic Reaction Mechanism Introduction

   1. 3.1 Review of Acids and Bases and Ka

   2. 3.2 Organic Acids and Bases and Organic Reaction Mechanism

   3. 3.3 pKa of Organic Acids and Application of pKa to Predict Acid-Base Reaction Outcome

   4. 3.4 Structural Effects on Acidity and Basicity

   5. 3.5 Lewis Acids and Lewis Bases

   6. Answers to Chapter 3 Practice Questions

6. Chapter 4: Conformations of Alkanes and Cycloalkanes

   1. 4.1 Conformation Analysis of Alkanes

   2. 4.2 Cycloalkanes and Their Relative Stabilities

   3. 4.3 Conformation Analysis of Cyclohexane

   4. 4.4 Substituted Cyclohexanes

   5. Answers to Chapter 4 Practice Questions

7. Chapter 5: Stereochemistry

   1. 5.1 Summary of Isomers

   2. 5.2 Geometric Isomers and the E/Z Naming System

   3. 5.3 Chirality and the R/S Naming System

   4. 5.4 Optical Activity

   5. 5.5 Fisher Projection

   6. 5.6 Compounds with More Than One Chirality Centers

   7. Answers to Chapter 5 Practice Questions

8. Chapter 6: Structural Identification of Organic Compounds: IR and NMR Spectroscopy

   1. 6.1 Electromagnetic Radiation and Molecular Spectroscopy

   2. 6.2 Infrared (IR) Spectroscopy Theory

   3. 6.3 IR Spectrum and Characteristic Absorption Bands

   4. 6.4 IR Spectrum Interpretation Practice

   5. 6.5 NMR Theory and Experiment

   6. 6.6 ¹H NMR Spectra and Interpretation (Part I)

   7. 6.7 ¹H NMR Spectra and Interpretation (Part II)

   8. 6.8 ¹³C NMR Spectroscopy

   9. 6.9 Structure Determination Practice

   10. Answers to Chapter 6 Practice Questions

9. Chapter 7: Nucleophilic Substitution Reactions

   1. 7.1 Nucleophilic Substitution Reactions Overview

   2. 7.2 SN2 Reaction Mechanisms, Energy Diagram and Stereochemistry

   3. 7.3 Other Factors that Affect SN2 Reactions

   4. 7.4 SN1 Reaction Mechanisms, Energy Diagram and Stereochemistry

   5. 7.5 SN1 vs SN2

   6. 7.6 Extra Topics on Nucleophilic Substitution Reactions

   7. Answers to Chapter 7 Practice Questions

10. Chapter 8: Elimination Reactions

    1. 8.1 E2 Reactions

    2. 8.2 E1 Reactions

    3. 8.3 E1/E2 Summary

    4. 8.4 Comparison and Competition Between SN1, SN2, E1 and E2

    5. Answers to Chapter 8 Practice Questions

11. Chapter 9: Free Radical Substitution Reaction of Alkanes

    1. 9.1 Homolytic and Heterolytic Cleavage

    2. 9.2 Halogenation Reaction of Alkanes

    3. 9.3 Stability of Alkyl Radicals

    4. 9.4 Chlorination vs Bromination

    5. 9.5 Stereochemistry for the Halogenation of Alkanes

    6. 9.6 Synthesis of Target Molecules: Introduction to Retrosynthetic Analysis

    7. Answers to Chapter 9 Practice Questions

12. Chapter 10: Alkenes and Alkynes

    1. 10.1 Synthesis of Alkenes

    2. 10.2 Reactions of Alkenes: Addition of Hydrogen Halide to Alkenes

    3. 10.3 Reactions of Alkenes: Addition of Water (or Alcohol) to Alkenes

    4. 10.4 Reactions of Alkenes: Addition of Bromine and Chlorine to Alkenes

    5. 10.5 Reaction of Alkenes: Hydrogenation

    6. 10.6 Two Other Hydration Reactions of Alkenes

    7. 10.7 Oxidation Reactions of Alkenes

    8. 10.8 Alkynes

    9. Answers to Chapter 10 Practice Questions

13. About the Author