Organic Chemistry
Francis A. Carey
JN 10th Edition
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, Table of Contents
Part I: The Basics
1. Structure and Bonding
• Atomic structure and covalent bonding
• Hybridization and molecular geometry
• Resonance structures
• Polarity of molecules
2. Acids and Bases
• Brønsted–Lowry and Lewis definitions
• pKa and acid–base equilibria
• Predicting reaction direction
• Organic acids and bases
3. An Introduction to Organic Compounds
• Alkanes and functional groups
• Representing organic molecules
• Naming alkanes
• Physical properties and isomerism
4. Alkanes and Cycloalkanes
• Structure and conformations
• Ring strain and stability
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• Conformations of cyclohexane
• Sources and uses of alkanes
5. Stereochemistry
• Chirality and optical activity
• Enantiomers and diastereomers
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• R/S configuration system
• Fischer projections
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Part II: Reactions and Mechanisms
6. Understanding Organic Reactions
• Types of organic reactions
• Mechanisms and reaction intermediates
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• Energy diagrams and kinetics
• Reaction coordinate and transition state
7. Alkenes and Alkynes I: Properties and Synthesis
• Structure and stability
• Elimination reactions (E1 and E2)
• Synthesis of alkenes and alkynes
• Catalytic hydrogenation
8. Alkenes and Alkynes II: Addition Reactions
• Electrophilic additions
• Hydration, hydroboration–oxidation
• Halogenation and polymerization
• Regiochemistry and stereochemistry
9. Nucleophilic Substitution and Elimination Reactions
• SN1, SN2, E1, and E2 mechanisms
• Factors influencing reactivity
• Solvent effects
• Competing reactions
10. Radical Reactions
• Radical formation and stability
• Halogenation of alkanes
• Radical addition and polymerization
Part III: Functional Group Chemistry
, 11. Alcohols and Ethers
• Structure and physical properties
• Preparation and reactions of alcohols
• Oxidation reactions
• Williamson ether synthesis
12. Infrared and Mass Spectrometry
• Principles of IR spectroscopy
• Characteristic absorptions
• Mass spectrometry fragmentation patterns
13. Nuclear Magnetic Resonance (NMR) Spectroscopy
• ¹H and ¹³C NMR spectroscopy
• Chemical shifts and coupling constants
• Using NMR to deduce structure
14. Aromatic Compounds
• Structure and stability of benzene
• Huckel’s rule and aromaticity
• Aromatic compounds and their nomenclature
15. Reactions of Aromatic Compounds
• Electrophilic aromatic substitution
• Activating/deactivating groups
• Orientation effects and synthetic applications
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Part IV: Carbonyl Compounds
16. Aldehydes and Ketones I: Nucleophilic Addition Reactions
• Structure and reactivity
• Hydration, acetal, and imine formation
• Grignard reactions
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17. Aldehydes and Ketones II: Oxidation–Reduction and Related Reactions
• Oxidation of aldehydes
• Reduction reactions
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• Enolization and tautomerism
18. Carboxylic Acids and Their Derivatives
• Acidity and hydrogen bonding
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• Nucleophilic acyl substitution
• Derivatives: esters, amides, anhydrides, acid chlorides
19. Reactions of Carboxylic Acid Derivatives
• Transesterification, hydrolysis, and aminolysis
• Reduction and Grignard reactions
• Acyl substitution mechanisms
20. Carbanion Chemistry: Enols and Enolates
• Keto–enol tautomerism
• Enolate formation and reactions
• Aldol and Claisen condensations
Part V: Biomolecules and Advanced Topics
21. Amines and Heterocycles
• Structure and basicity of amines
• Reactions and synthesis
• Aromatic amines and heterocyclic chemistry
22. Phenols and Aryl Halides
• Acidity and reactivity of phenols
• Nucleophilic aromatic substitution
• Synthesis and reactions of aryl halides
23. Carbohydrates
• Structure and stereochemistry of monosaccharides
• Glycosidic bonds and disaccharides
, • Polysaccharides and biological significance
24. Amino Acids, Peptides, and Proteins
• Structure and properties of amino acids
• Peptide bond formation
• Levels of protein structure
25. Lipids
• Fatty acids, triglycerides, phospholipids
• Steroids and biological membranes
• Lipid metabolism overview
26. Synthetic Polymers
• Addition and condensation polymers
• Copolymers and polymer properties
• Biodegradable polymers
27. Organic Synthesis and Retrosynthetic Analysis
• Functional group transformations
• Multistep synthesis planning
• Protecting groups and synthetic strategy
Appendices
• Appendix A: Summary of Organic Nomenclature
• Appendix B: Physical Constants
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• Appendix C: Common pKa Values
• Appendix D: Spectral Data Tables
• Appendix E: Answers to Selected Problems
• Glossary
• Index
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