Concise and manageable, Fessenden and Fessenden's text has earned a reputation as a superb teaching text. One of the only books that students can get through cover to cover in two semesters, it is written in an economical style that stays focused on the main discussion. The authors anticipate student questions and answer them in the same chapter. Described by users as " the masters of the short sentence." Fessenden and Fessenden are renowned for their clear, to-the-point coverage and masterful selection of topics. The book provides a clear organization of functional groups according to sigma-bonding and pi-bonding to give students a conceptually efficient context that helps them understand the overall content of organic chemistry. Core topics for the course appear in Chapters 1-18 with more advanced and biochemical topics covered in 19-26. Essential information in each chapter is covered in earlier sections, leaving optional material for later sections.
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Table of Contents
1. ATOMS AND MOLECULES-A REVIEW Electron Structure of the Atom / Atomic Radius / Electronegativity / Introduction to the Chemical Bond / Chemical Formulas in Organic Chemistry / Attractions Between Molecules / Acids and Bases 2. ORBITALS AND THEIR ROLE IN COVALENT BONDING Properties of Waves / Bonding in Hydrogen / Some General Features of Bonding and Antibonding Orbitals / Hybrid Orbitals of Carbon / Functional Groups / Hybrid Orbitals of Nitrogen and Oxygen / Conjugated Double Bonds / Benzene / Resonance 3. STRUCTURAL ISOMERISM, NOMENCLATURE, AND ALKANES Structural Isomers / How Organic Nomenclature Developed / A Survey of Organic Nomenclature / Alkenes / The Hydrocarbon Resources 4. STEREOCHEMISTRY Geometric Isomerism in Alkenes / Geometric Isomerism in Cyclic Compounds / Conformations of Open-Chain Compounds / Shapes of Cyclic Compounds / The Conformers of Cyclohexane / Chirality / Rotation of Plane-Polarized Light / Assignment of Configuration: the and (S) System / More Than One Chiral Carbon / Prochirality / Resolution of a Racemic Mixture 5. ALKYL HALIDES; SUBSTITUTION AND ELIMINATION REACTIONS Types of Organohalogen Compounds / Nomenclature and Classification of Alklyl Halides / A Preview of Substitution and Elimination Reactions / The SN2 Reaction / The SN1 Reaction / Substitution Reactions of Allylic Halides and Benzylic Halides / The E1 Reaction / The E2 Reaction / Factors Governing Substitution and Elimination Reactions / Synthesizing Other Compounds from Alkyl Halides 6. FREE-RADICAL REACTIONS A Typical Radical Reaction: Chlorination of Methane / Relative Reactivities of Halogens / Stereochemistry of Radical Halogenation / Hydrogen Abstraction: The Rate-Determining Step / Selective Radical Halogenations / Other Radical Reactions / Free-Radical Initiators and Inhibitors / Polymers 7. ALCOHOLS Nomenclature and Classification of Alcohols / Basicity and Acidity of Alcohols / Preparation of Alcohols / Substitution Reactions of Alcohols / Other Reagents Used to Convert Alcohols to Alkyl Halides / Elimination Reactions of Alcohols / Esters of Alcohols / Oxidation of Alcohols / Use of Alcohols in Synthesis / Synthesis Problems 8. ETHERS, EPOXIDES, AND SULFIDES Nomenclature of Ethers and Epoxides / Preparation of Ethers and Epoxides / Substitution Reactions of Ehters / Substitution Reactions of Epoxides / Crown Ethers / Thiols and Sulfides 9. SPECTROSCOPY I: INFRARED AND NUCLEAR MAGNETIC RESONANCE Electromagnetic Radiation / Features of a Spectrum / Absorption of Infrared Radiation / The Infrared Spectrum / Interpretation of Infrared Spectra / Nuclear Magnetic Resonance Spectra / Nuclear Magnetic Resonance Spectroscopy / Types of Induced Molecular Magnetic Fields / Counting the Protons / Spin-Spin Coupling / Splitting Patterns / Spin-Spin Splitting Diagrams / Carbon-13 NMR Spectroscopy / Using Infrared and NMR Spectra for the Identification of Organic Structures 10. ALKENES AND ALKYNES Bonding in Alkenes and Alkynes; Acidity of Alkynes / Nomenclature of Alkenes and Alkynes / Spectra of Alkenes and Alkynes / Preparation of Alkenes and Alkynes / Preview of Addition Reactions / Addition of Hydrogen Halides to Alkenes and Alkynes / Addition of H2SO4 and H20 to Alkenes and Alkynes / Hydration Using Mercuric Acetate / Addition of Borane Alkenes / Addition of Halogens to Alkenes and Alkynes / Addition of Carbenes to Alkenes / Catalytic Hydrogenation / Oxidation of Alkenes / Use of Alkenes and Alkynes in Synthesis 11. AROMATICITY AND BENZENE; ELECTROPHILIC AROMATIC SUBSTITUTION Nomenclature of Substituted Benzenes / Spectra of Substituted Benzenes / Stability of the Benzene Ring / The Bonding in Benzene / What is an Aromatic Compound? / Requirements for Aromaticity / Electrophilic Aromatic Substitution / The First Substitution / The Second Substitution / The Third Substitution 12. SUBSTITUTED BENZENES Alkylbenzenes / Phenols / Benzenediazonium Salts / Halobenzenes and Nucleophilic Aromatic Substitution / Synthesis Using Substituted Benzene Compounds 13. ALDEHYDES AND KETONES Nomenclature of Aldehydes and Ketones / Preparation of Aldehydes and Ketones / Spectral Properties of Aldehydes and Ketones / Addition Reactions of Aldehydes and Ketones / Addition-Elimination Reactions of Aldehydes and Ketones / Reduction of Aldehydes and Ketones / Oxidation of Aldehydes and Ketones / Reactivity of the Alpha Hydrogens / Tautomerism / Alpha Halogenation / Use of Aldehydes and Ketones in Synthesis 14. CARBOXYLIC ACIDS Nomenclature of Carboxylic Acids / Spectral Properties of Carboxylic Acids / Preparation of Carboxylic Acids / How Structure Affects Acid Strength / Reaction of Carboxylic Acids with Bases / Esterification of Carboxylic Acids / Reduction of Carboxylic Acids / Polyfunctional Carboxylic Acids / Use of Carboxylic Acids in Synthesis 15. DERIVATIVES OF CARBOXYLIC ACIDS Reactivity of Carboxylic Acid Derivatives / Spectral Properties of Carboxylic Acid Derivatives / Acid Halides / Anhydrides of Carboxylic Acids / Esters of Carboxylic Acids / Lactones / Polyesters / Amides / Polyamides / Compounds Related to Amides / Nitriles / Use of Carboxylic Acid Derivatives in Synthesis 16. CONJUGATE ADDITION Conjugate Pi Bonds / 1,2-Addition and 1,4-Addition to Conjugated Dienes / The Diels-Alder Reaction / 1,4-Addition to a,b- Unsaturated Carbonyl Compounds 17. ENOLATES AND CARBANIONS: BUILDING BLOCKS FOR ORGANIC SYNTHESIS Acidity of the Alpha Hydrogen / Alkylation of Malonic Ester / Alkylation of Acetoacetic Ester / Syntheses Using Alkylation Reactions / Alkylation and Acylation of Enamines / Aldol Condensations / Reactions Related to the Aldol Condensation / Ester Condensations / Nucleophilic Addition to a, b-Unsaturated Carbonyl Compounds 18. AMINES Classification and Nomenclature of Amines / Bonding in Amines / Spectral Properties of Amines / Preparation of Amines / Basicity of Amines / Amine Salts / Substitution Reactions with Amines / Reactions of Amines with Nitrous Acid / Hofmann Elimination 19. POLYCLIC AND HETEROCYCLIC AROMATIC COMPOUNDS Nomenclature of Polycyclic Aromatic Compounds / Bonding in Polycyclic Aromatic Compounds / Oxidation of Polycyclic Aromatic Compounds / Reduction of Polycyclic Aromatic Compounds / Electrophilic Substitution Reactions of Napthalene / Nomenclature of Aromatic Heterocylic Compounds / Pyridine, a Six-Membered Aromatic Heterocycle / Quinoline and Isoquinoline / Pyrrole, a Five-Membered Aromatic Heterocycle 20. NATURAL PRODUCTS: STUDIES IN ORGANIC SYNTHESIS Terpenes / Pheromones: Synthesis of Chiral Natural Products / Alkaloids 21. PERICYCLIC REACTIONS Molecular Orbitals of Conjugated Polyenes / Cycloaddition Reactions / Electrocyclic Reactions / Sigmatropic Rearrangements / Pericyclic Reactions Leading to Vitamin D 22. SPECTROSCOPY II: ULTRAVIOLET SPECTRA, COLOR AND VISION, MASS SPECTRA Ultraviolet and Visible Spectra / Expressions Used in Ultraviolet Spectroscopy / Types of Electron Transitions / Color and Vision / Photochemistry / Mass Spectrometry / The Mass Spectrometer / Isotopes in Mass Spectra / Ionization and Fragmentation in Mass Spectra 23. CARBOHYDRATES Some Common Monosaccharides / Classification of the Monosaccharides / Configurations of the Monosaccharides / Cyclization of the Monosaccharides / Glycosides / Oxidation of Monosaccharides / Reduction of Monosaccharides / Reaction at the Hydroxyl Groups / Disaccharides / Polysaccharides 24. LIPIDS Fats and Oils / Soaps and Detergents / Phospholipids / Prostaglandins / Steroids 25. AMINO ACIDS AND PROTEINS The Structures of Amino Acids / Synthesis of Amino Acids / Reactions of Amino Acids / Peptides / Bonding in Peptides / Determination of Peptide Structure / Synthesis of Peptides / Classification of Proteins / Higher Structure of Proteins 26. NUCLEIC ACIDS Hydrolysis Products of the Nucleic Acids / Structure and Properties of DNA / Structure and Properties of RNA / The Role of RNA in Protein Biosynthesis / APPENDIX: NOMENCLATURE OF ORGANIC COMPOUNDS / ANSWERS TO PROBLEMS / INDEX