Organic Chemistry: Thinking with Molecules
Thinking with Molecules
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40 chapters
~21 hours total
74 pages
1
Front Matter
4 chapters2
Part I — Foundations
7 chapters- Part I — Foundations: The Language of Organic Chemistry
- Chapter 1 — What Is Organic Chemistry? Why Carbon Is Special and Why This Course Changes How You See the World
- Chapter 2 — Structure and Bonding: Lewis Structures, Hybridization, and Molecular Orbitals
- Chapter 3 — Acids and Bases: The Framework That Predicts Everything in Organic Chemistry
- Chapter 4 — Functional Groups and Nomenclature: The Vocabulary of Molecules
- Chapter 5 — Alkanes, Conformations, and an Introduction to Thermodynamics and Kinetics
- Chapter 6 — Seeing Molecules: Introduction to Spectroscopy (IR, MS, and the Logic of Structure Determination)
3
Part II — Stereochemistry
4 chapters4
Part III — Substitution and Elimination
6 chapters- Part III — Substitution and Elimination: The First Mechanisms
- Chapter 10 — Nucleophilic Substitution ($S_N2$): The Backside Attack
- Chapter 11 — Nucleophilic Substitution ($S_N1$): The Carbocation Pathway
- Chapter 12 — Elimination Reactions ($E2$ and $E1$): Competing with Substitution
- Chapter 13 — Predicting Substitution vs. Elimination: The Decision Framework
- Chapter 14 — Synthesis Workshop 1: Combining Substitution and Elimination Strategically
5
Part IV — Addition Reactions
6 chapters- Part IV — Addition Reactions
- Chapter 15 — Alkenes: Structure, Stability, and Electrophilic Addition
- Chapter 16 — Addition Reactions of Alkenes: The Full Toolbox
- Chapter 17 — Alkynes: Reactions and the Power of Triple Bonds
- Chapter 18 — Radical Reactions: A Different Mechanism, A Different Selectivity
- Chapter 19 — Conjugated Systems, Diels-Alder Reactions, and Orbital Symmetry
6
Part V — Aromatic Chemistry
5 chapters- Part V — Aromatic Chemistry
- Chapter 20 — Aromaticity: What Makes Benzene Special and How to Recognize It
- Chapter 21 — Electrophilic Aromatic Substitution: The Reactions of Benzene
- Chapter 22 — Substituent Effects: Directing Groups, Activating/Deactivating, and Multi-Step Aromatic Synthesis
- Chapter 23 — Nucleophilic Aromatic Substitution and Side-Chain Reactions
7
Part VI — Carbonyl Chemistry
9 chapters- Part VI — Carbonyl Chemistry: The Heart of Organic Reactivity
- Chapter 24 — The Carbonyl Group: Why It's the Most Important Functional Group in Organic Chemistry
- Chapter 25 — Nucleophilic Addition to Aldehydes and Ketones
- Chapter 26 — Nucleophilic Acyl Substitution: Carboxylic Acid Derivatives
- Chapter 27 — Enols, Enolates, and α-Carbon Chemistry
- Chapter 28 — Aldol Reactions and Claisen Condensations: Forming Carbon-Carbon Bonds
- Chapter 29 — Conjugate (Michael) Addition and the Robinson Annulation
- Chapter 30 — Amines: Nucleophilicity, Basicity, and the Chemistry of Nitrogen
- Chapter 31 — Synthesis Workshop 2: Retrosynthetic Analysis and Multi-Step Synthesis Design
8
Part VII — Bioorganic and Special Topics
5 chapters- Part VII — Bioorganic and Special Topics
- Chapter 32 — Carbohydrates: Structure, Reactivity, and Biological Significance
- Chapter 33 — Amino Acids, Peptides, and Proteins: The Chemistry of Life's Machines
- Chapter 34 — Lipids, Terpenes, and Biosynthesis: How Nature Does Organic Chemistry
- Chapter 35 — Organic Chemistry of Drug Design
9
Part VIII — Advanced Topics and Synthesis
6 chapters- Part VIII — Advanced Topics and Synthesis
- Chapter 36 — Oxidation and Reduction Reactions: A Unified View
- Chapter 37 — Organometallic Chemistry: Transition Metal Catalysis and Modern Synthesis
- Chapter 38 — The Art of Synthesis: Retrosynthetic Thinking, Strategy, and the Beauty of Total Synthesis
- Chapter 39 — Pericyclic Reactions and Woodward-Hoffmann Rules
- Chapter 40 — Green Chemistry, Flow Chemistry, and the Future of Synthesis
10
Appendices
15 chapters- Glossary
- Answers to Selected Exercises
- Bibliography
- Index
- Appendix A — Periodic Table and Atomic Data
- Appendix B — pKa Reference Table
- Appendix C — Common Reaction Summary (by mechanism family)
- Appendix D — Spectroscopy Reference
- Appendix E — Computational Chemistry Software Setup
- Appendix F — Named Reactions Reference
- Appendix G — Retrosynthesis Disconnections
- Appendix H — IUPAC Nomenclature Quick Reference
- Appendix I — Reagents and Solvents Reference
- Appendix J — Laboratory Safety
- Appendix K — Careers and Graduate School in Chemistry
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