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Organic Chemistry: Thinking with Molecules
Thinking with Molecules
74
Pages
67
Chapters
10
Parts
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About This Book
Table of Contents
Front Matter
1.
Preface
2.
How to Use This Book
3.
Prerequisites
4.
Acknowledgments
Part I — Foundations
1.
Part I — Foundations: The Language of Organic Chemistry
2.
Chapter 1 — What Is Organic Chemistry? Why Carbon Is Special and Why This Course Changes How You See the World
3.
Chapter 2 — Structure and Bonding: Lewis Structures, Hybridization, and Molecular Orbitals
4.
Chapter 3 — Acids and Bases: The Framework That Predicts Everything in Organic Chemistry
5.
Chapter 4 — Functional Groups and Nomenclature: The Vocabulary of Molecules
6.
Chapter 5 — Alkanes, Conformations, and an Introduction to Thermodynamics and Kinetics
7.
Chapter 6 — Seeing Molecules: Introduction to Spectroscopy (IR, MS, and the Logic of Structure Determination)
Part II — Stereochemistry
1.
Part II — Stereochemistry
2.
Chapter 7 — Stereoisomerism: Chirality, Enantiomers, and Diastereomers
3.
Chapter 8 — Stereochemistry in Reactions: Why 3D Shape Determines Biological Activity
4.
Chapter 9 — NMR Spectroscopy: The Most Powerful Tool for Determining Molecular Structure
Part III — Substitution and Elimination
1.
Part III — Substitution and Elimination: The First Mechanisms
2.
Chapter 10 — Nucleophilic Substitution ($S_N2$): The Backside Attack
3.
Chapter 11 — Nucleophilic Substitution ($S_N1$): The Carbocation Pathway
4.
Chapter 12 — Elimination Reactions ($E2$ and $E1$): Competing with Substitution
5.
Chapter 13 — Predicting Substitution vs. Elimination: The Decision Framework
6.
Chapter 14 — Synthesis Workshop 1: Combining Substitution and Elimination Strategically
Part IV — Addition Reactions
1.
Part IV — Addition Reactions
2.
Chapter 15 — Alkenes: Structure, Stability, and Electrophilic Addition
3.
Chapter 16 — Addition Reactions of Alkenes: The Full Toolbox
4.
Chapter 17 — Alkynes: Reactions and the Power of Triple Bonds
5.
Chapter 18 — Radical Reactions: A Different Mechanism, A Different Selectivity
6.
Chapter 19 — Conjugated Systems, Diels-Alder Reactions, and Orbital Symmetry
Part V — Aromatic Chemistry
1.
Part V — Aromatic Chemistry
2.
Chapter 20 — Aromaticity: What Makes Benzene Special and How to Recognize It
3.
Chapter 21 — Electrophilic Aromatic Substitution: The Reactions of Benzene
4.
Chapter 22 — Substituent Effects: Directing Groups, Activating/Deactivating, and Multi-Step Aromatic Synthesis
5.
Chapter 23 — Nucleophilic Aromatic Substitution and Side-Chain Reactions
Part VI — Carbonyl Chemistry
1.
Part VI — Carbonyl Chemistry: The Heart of Organic Reactivity
2.
Chapter 24 — The Carbonyl Group: Why It's the Most Important Functional Group in Organic Chemistry
3.
Chapter 25 — Nucleophilic Addition to Aldehydes and Ketones
4.
Chapter 26 — Nucleophilic Acyl Substitution: Carboxylic Acid Derivatives
5.
Chapter 27 — Enols, Enolates, and α-Carbon Chemistry
6.
Chapter 28 — Aldol Reactions and Claisen Condensations: Forming Carbon-Carbon Bonds
7.
Chapter 29 — Conjugate (Michael) Addition and the Robinson Annulation
8.
Chapter 30 — Amines: Nucleophilicity, Basicity, and the Chemistry of Nitrogen
9.
Chapter 31 — Synthesis Workshop 2: Retrosynthetic Analysis and Multi-Step Synthesis Design
Part VII — Bioorganic and Special Topics
1.
Part VII — Bioorganic and Special Topics
2.
Chapter 32 — Carbohydrates: Structure, Reactivity, and Biological Significance
3.
Chapter 33 — Amino Acids, Peptides, and Proteins: The Chemistry of Life's Machines
4.
Chapter 34 — Lipids, Terpenes, and Biosynthesis: How Nature Does Organic Chemistry
5.
Chapter 35 — Organic Chemistry of Drug Design
Part VIII — Advanced Topics and Synthesis
1.
Part VIII — Advanced Topics and Synthesis
2.
Chapter 36 — Oxidation and Reduction Reactions: A Unified View
3.
Chapter 37 — Organometallic Chemistry: Transition Metal Catalysis and Modern Synthesis
4.
Chapter 38 — The Art of Synthesis: Retrosynthetic Thinking, Strategy, and the Beauty of Total Synthesis
5.
Chapter 39 — Pericyclic Reactions and Woodward-Hoffmann Rules
6.
Chapter 40 — Green Chemistry, Flow Chemistry, and the Future of Synthesis
Appendices
1.
Glossary
2.
Answers to Selected Exercises
3.
Bibliography
4.
Index
5.
Appendix A — Periodic Table and Atomic Data
6.
Appendix B — pKa Reference Table
7.
Appendix C — Common Reaction Summary (by mechanism family)
8.
Appendix D — Spectroscopy Reference
9.
Appendix E — Computational Chemistry Software Setup
10.
Appendix F — Named Reactions Reference
11.
Appendix G — Retrosynthesis Disconnections
12.
Appendix H — IUPAC Nomenclature Quick Reference
13.
Appendix I — Reagents and Solvents Reference
14.
Appendix J — Laboratory Safety
15.
Appendix K — Careers and Graduate School in Chemistry
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