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An Introduction To The Study Of Organic Chemistry | |
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Electronic Structure and Bonding Acids and Bases | |
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The Structure of an Atom | |
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The Distribution of Electrons in an Atom | |
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Ionic, Covalent, and Polar Bonds | |
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Representation of a Structure | |
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Atomic Orbitals | |
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An Introduction to Molecular Orbital Theory | |
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Bonding in Methane and Ethane: Single Bonds | |
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Bonding in Ethane: A Double Bond | |
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Bonding in Ethyne: A Triple Bond | |
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Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion | |
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Bonding in Water | |
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Bonding in Ammonia and the Ammonium Ion | |
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Bonding in the Hydrogen Halides | |
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Summary: Orbital Hybridization, Bond Lengths, Bond Strengths, and Bond Angles | |
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Dipole Moments of Molecules | |
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An Introduction to Acids and Bases | |
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Organic Acids and Bases pK | |
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A and pH | |
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The Effect of Structure on pK | |
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A An Introduction to Delocalized Electrons and Resonance | |
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The Effect of pH on the Structure of an Organic Compound | |
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Lewis Acids and Bases | |
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An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure | |
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Nomenclature of Alkyl Substituents | |
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Nomenclature of Alkanes | |
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Nomenclature of Cycloalkanes | |
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Nomenclature of Alkyl Halides | |
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Nomenclature of Ethers | |
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Nomenclature of Alcohols | |
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Nomenclature of Amines | |
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Structures of Alkyl Halides, Alcohols, Ethers, and Amines | |
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Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines | |
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Conformations of Alkanes: Rotation About Carbon-Carbon Bonds | |
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Cycloalkanes: Ring Strain | |
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Conformations of Cyclohexane | |
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Conformations of Monosubstituted Cyclohexanes | |
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Conformations of Disubstituted Cyclohexanes | |
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Conformations of Fused Rings | |
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Hydrocarbons, Stereochemistry, And Resonance | |
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Alkenes: Structure, Nomenclature, and an Introduction to Reactivity Thermodynamics and Kinetics | |
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Molecular Formula and the Degree of Unsaturation | |
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Nomenclature of Alkenes | |
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The Structure of Alkenes | |
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Cis- Trans Isomerism | |
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The E,Z | |
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System of Nomenclature | |
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How Alkenes React | |
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Curved Arrows | |
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Thermodynamics and Kinetics | |
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Reactions of Alkenes | |
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Addition of Hydrogen Halides | |
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Carbocation Stability | |
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The Structure of the Transition State | |
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Regioselectivity of Electophilic Addition Reactions | |
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Addition of Water and Addition of Alcohols | |
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Rearrangement of Carbocations | |
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Addition of Halogens | |
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Oxymercuration-Reduction and Alkoxymercuration-Reduction | |
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Addition of Borane: Hydroboration-Oxidation | |
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Addition of Radicals | |
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The Relative Stabilities of Radicals | |
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Addition of Hydrogen | |
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The Relative Stabilities of Alkenes | |
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Reactions and Synthesis | |
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Stereochemistry: The Arrangement of Atoms in Space | |
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The Stereochemistry of Addition Reactions | |
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Cis-Trans Isomers | |
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Chirality | |
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Asymmetric Carbon, Chirality Centers, and Stereocenters | |
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Isomers with One Asymmetric Carbon | |
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Drawing Enantiomers | |
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Naming Enantiomers: The R, S | |
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System of Nomenclature | |
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Optical Activity | |
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Optical Purity and Enantiomeric Excess | |
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Isomers with More Than One Asymmetric Carbon | |
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Meso Compounds | |
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The R, S | |
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System of Nomenclature for Isomers with More Than One Asymmetric Carbon | |
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Reactions of Compounds that Contain an Asymmetric Carbon | |
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The Absolute Configuration of (+)- Glyceraldehyde | |
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Separating Enantiomers | |
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Discrimination of Enantiomers by Biological Molecules | |
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Enantiotopic Hydrogens, Diastereotopic Hydrogens, and Prochiral Carbons | |
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Nitrogen and Phosphorus Asymmetric Carbons | |
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Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions | |
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Stereochemistry of Electrophilic Addition Reactions of Alkenes | |
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Stereochemistry of Enzyme-Catalyzed Reactions | |
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Reactions of Alkynes Introduction to Multistep Synthesis | |
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Nomenclature of Alkynes | |
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Physical Properties of Unsaturated Hydrocarbons | |
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The Structure of Alkynes | |
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How Alkynes React | |
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Addition of Hydrogen Halides and Addition of Halogens | |
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Addition of Water | |
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Addition of Borane: Hydroboration-Oxidation | |
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Addition of Hydrogen | |
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Acidity of a Hydrogen Bonded to an SP | |
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Hybridized Carbon | |
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Synthesis Using Acetylide Ions | |
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Designing a Synthesis I: An Introduction to Multistep Synthesis | |
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Commercial Use of Ethyne | |
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Electron Delocalization and Resonance More About Molecular Orbital Theory | |
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Delocalized Electrons: the Structure of Benzene | |
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The Bonding In Benzene | |
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Resonance Contributors and the Resonance Hybrid | |
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Drawing Resonance Contributors | |
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Predicted Stabilites of Resonance Contributors | |
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Resonance Energy | |
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Stability of Allylic and Benzylic Cations | |
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Stability of Allylic and Benzylic Radicals | |
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Some Chemical Consequences of Electron Delocalization | |
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The Effect of Electron Delocalization on pK | |
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A Molecular Orbital Description of Stability | |
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Reactions of Dienes Ultraviolet/Visible Spectroscopy | |
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Nomenclature of Alkenes with More than One Functional Group | |
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Configurational Isomers of Dienes | |
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Relative Stabilities of Dienes | |
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How Dienes React | |
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Electrophilic Addition Reactions of Isolated Dienes | |
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Electrophilic Addition Reactions of Conjugated Dienes | |
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Thermodynamic Versus Kinetic Control of Reactions | |
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The Diels-Alder Reaction: A 1,4-Addition Reaction | |
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Ultraviolet and Visible Spectroscopy | |
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The Beer-Lambert Law | |
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Effect of Conjugation on Imax | |
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The Visible Spectrum and Color | |
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Uses of UV/VIS Spectroscopy | |
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Substitution And Elimination Reactions | |
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Reactions of Alkanes: Radicals | |
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The Low Reactivity of Alkanes | |
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Chlorination and Bromination of Alkanes | |
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Factors that Determine Product Distribution | |
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The Reactivity-Selectivity Principle | |
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Radical Substitution of Benzylic and Allylic Hydrogens | |
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Stereochemistry of Radical Substitution Reactions | |
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Reactions of Cyclic Compounds | |
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Radicals Reactions in Biological Systems | |
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Radicals and Stratospheric Ozone | |
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Substitution Reactions of Alkyl Halides | |
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Reactivity Considerations | |
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The Mechanism of SN2 Reactions | |
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The SN2 Reaction | |
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The Reversibility of an SN2 Reaction | |
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The Mechanism of SN1 Reaction | |
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The SN1 Reaction | |
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The Stereochemistry of SN2 and SN1 Reactions | |
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Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides | |
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Competition Between SN2 and SN1 Reactions | |
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The Role of the Solvent in SN1 and SN1 Reactions | |
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Biological Methylating Reagents | |
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Elimination Reactions of Alkyl Halides | |
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Competition Between Substitution and Elimination | |
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The E2 Reaction | |
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The Regioselectivity of the E2 Reaction | |
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The E1 Reaction | |
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Competition Between E2 and E1 Reactions | |
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Stereochemistry of E2 and E1 Reactions | |
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Elimination from Cyclic Compounds | |
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A Kinetic Isotope Effect | |
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Competition Between Substitution and Elimination | |
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Substitution and Elimination Reactions in Synthesis | |
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Consecutive E2 Elimination Reactions | |
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Intermolecular versus Intramolecular Reactions | |
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Designing a Synthesis II: Approaching the Problem | |
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Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds Organometallic Compounds | |
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Substitution Reactions of Alcohol | |
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Amines Do Not Undergo Substitution Reactions | |
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Other Methods Used to Convert Alcohols Into Alkyl Halides | |
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Converting Alcohols into Sulfonates | |
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Dehydration of Alcohols | |
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Substitution Reactions of Ethers | |
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Reactions of Epoxides | |
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Arene Oxides | |
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Crown Ethers | |
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Thiols, Sulfides, and Sulfonium Salts | |
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Organometallic Compounds | |
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Coupling Reactions | |
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Identification Of Organic Compounds | |
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Mass Spectrometry and Infrared Spectroscopy | |
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Mass Spectrometry | |
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The Mass Spectrum | |
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Fragmentation | |
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Isotopes in Mass Spectrometry | |
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Determination of Molecular Formulas: High-Resolution Mass Spectrometry | |
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Fragmentation at Functional Groups | |
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Spectroscopy and the Electromagnetic Spectrum | |
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Infrared Spectroscopy | |
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Infrared Absorption Bands | |
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Intensity of Absorption Bands | |
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Position of Absorption Bands | |
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C-H Absorption Bands | |
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Shape of Absorption Bands | |
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Absence of Absorption Bands | |
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Infrared Inactive Vibrations | |
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Identifying Infrared Spectra | |
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NMR Spectroscopy | |
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Introduction to NMR Spectroscopy | |
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Fourier Transform NMR | |
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Shielding | |
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The Number of Signals in the 1H NMR Spectrum | |
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The Chemical Shift | |
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The Relative Position of 1H NMR Signals | |
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Characteristic Values of Chemical Shifts | |
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Integration of the NMR Signals | |
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Diamagnetic Anisotropy | |
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Splitting of the Signals | |
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More Examples of 1H NMR Spectra | |
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Coupling Constants | |
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Splitting Diagrams | |
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Time Dependence of NMR Spectroscopy | |
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Protons Bonded to Oxygen and Nitrogen | |
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Use of Deuterium in 1H NMR Spectroscopy | |
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Resolution of 1H NMR Spectra | |
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13C NMR Spectroscopy | |
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DEPT 13C NMR Spectra | |
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Two-Dimensional NMR Spectroscopy | |
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Magnetic Resonance Imaging | |
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Aromatic Compounds | |
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Aromaticity Reactions of Benzene | |
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Criteria for Aromaticity | |
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Aromatic Hydrocarbons | |
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Aromatic Heterocyclic Compounds | |
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Some Chemical Consequences of Aromaticity | |
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Antiaromaticity | |
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A Molecular Orbital Description of Aromaticity and Antiaromaticity | |
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Nomenclature of Monosubstituted Benzenes | |
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How Benzene Reacts | |
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General Mechanism for Electrophilic Aromatic Substitution Reactions | |
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Halogenation of Benzene | |
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Nitration of Benzene | |
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Sulfonation of Benzene | |
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Friedel-Crafts Alkylation of Benzene | |
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Friedel-Crafts Alkylations of Benzene | |
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Alkylations of Benzene by Acylation-Reduction | |
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Reactions of Substituted Benzenes | |
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Nomenclature of Diubstituted and Polysubstituted Benzenes | |
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Reactions of Substituents on Benzene | |
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The Effect of Substituents on Reactivity | |
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The Effect of Substituents on Orientation | |
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The Effect of Substituents on pK | |
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The Ortho/Para Ratio | |
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Additional Considerations Regarding Substituent Effects | |
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Designing a Synthesis III: Synthesis of Monosubstituted and Disubstituted Benzenes | |
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Synthesis of Trisubstituted Benzenes | |
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Synthesis of Substituted Benzenes Using Arenediazonium Salts | |
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The Arenediazonium Ion as an Electrophile | |
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Mechanism for the Reaction of Amines with Nitrous Acid | |
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Nucleophilic Aromatic Substitution Reactions | |
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Benzyne | |
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Polycyclic Benzenoid Hydrocarbons | |
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Electrophilic Substitution Reactions of Naphthalene and Substituted Naphthalenes | |
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Carbonyl Compounds | |
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Carbonyl Compounds I: Nucleophilic Acyl Substitution | |
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Nomenclature | |
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Structures of Carboxylic Acids and Carboxylic Acid Derivatives | |
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Physical Properties of Carbonyl Compounds | |
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Naturally Occurring Carboxylic Acids and Carobxylic Acid Derivatives | |
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How Class I Carbonyl Compounds React | |
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Relative Reactivities of Carboxylic Acids, Acyl Halides, and Carboxylic Acid Derivatives | |
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General Mechanism for Nucleophilic Acyl Substitution Reactions | |
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Reactions of Acyl Halides | |
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Reactions of Acid Anhydrides | |
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Reactions of Esters | |
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Acid-Catalyzed Ester Hydrolysis | |
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Hydroxide-Ion-Promotes Ester Hydrolysis | |
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Soaps, Detergents, and Micelles | |
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Reactions of Carboxylic Acids | |
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Reactions of Amides | |
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Acid-Catalyzed Hydrolysis of Amides | |
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Hydrolysis of an Imide- The Gabriel Synthesis | |
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Hydrolysis of Nitriles | |
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Designing a Synthesis IV: The Synthesis of Cyclic Compounds | |
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Synthesis of Carboxylic Acid Derivatives | |
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Dicarboxylic Acids and Their Derivatives | |
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Carbonyl Compounds II: Nucleophilic Acyl Addition, Nucleophilic Acyl Substitution, and Nucleophilic Addition-Elimination Reactions of <F128>a, <F128>b-Unsaturated Carbonyl Compounds | |
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Nomenclature | |
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Relative Reactivities of Carbonyl Compounds | |
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How Aldeyhdes and Ketones React | |
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Reactions of Carbonyl Compounds with Carbon Nucleophiles | |
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Reactions of Carbonyl Compounds with Hydride Ion | |
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Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles | |
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Reactions of Aldehydes and Ketones with Oxygen Nucleophiles | |
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Protecting Groups | |
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Addition of Sulfur Nucleophiles | |
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The Wittig Reaction | |
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Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces | |
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Designing a Synthesis V: The Synthesis of Cyclic Compounds | |
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Nucleophilic Addition to -Unsaturated Aldehydes and Ketones: Direct Addition Versus Conjugate Addition | |
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Nucleophilic Addition to <F128>a, <F128>b-Unsaturated Carboxylic Acid Derivatives | |
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Enzyme-Catalyzed Additions to <F128>a, <F128>b-Unsaturated Carbonyl Compounds | |
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Carbonyl Compounds III: Reactions at the <F128>a-Carbon | |
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Acidity of <F128>a-Hydrogens | |
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Keto-Enol Tautomerism | |
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How Enols and Enolate Ions React | |
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Halogenation of the <F128>a-Carbon of Aldehydes and Ketones | |
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Halogenation of the <F128>a-Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction | |
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<F128>a-Halogenated Carbonyl Compounds in Synthesis | |
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Using LDA to Form an Enolate | |
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Alkylation of the <F128>a-Carbon of Carbonyl Compounds | |
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Alkylation and Acylation of the <F128>a-Carbon via an Enamine Intermediate | |
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Alkylation of the <F128>b-Carbon: The Michael Reaction | |
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The Aldol Addition | |
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Dehydration of Aldol Addition Products: Formation of <F128>a, <F128>b-Unsaturated Aldehydes and Ketones | |
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The Mixed Aldol Addition | |
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The Claisen Condensation | |
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The Mixed Claisen Condensation | |
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Intramolecular Condensation and Addition Reactions | |
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Decarboxylation of 3-Oxocarboxylic Acids | |
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The Malonic Ester Synthesis: Synthesis of Carboxylic Acids | |
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The Acetoacetic Ester Synthesis: Synthesis of Methyl Ketones | |
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Designing a Synthesis VI: Making New Carbon-Carbon Bonds | |
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Reactions at the <F128>a-Carbon in Biological Systems | |
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Bioorganic Compounds | |
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More About Oxidation-Reduction Reactions | |
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Reduction Reactions | |
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Oxidation of Alcohols | |
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Oxidation of Aldehydes and Ketones | |
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Oxidation of Alkenes with Peroxyacids | |
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Hydroxylation of Alkenes | |
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Oxidative Cleavage of 1,2-Diols | |
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Oxidative Cleavage of Alkenes: Ozonolysis | |
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Oxidative Cleavage of Alkynes | |
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Designing a Synthesis VII: Functional Group Interconversion | |
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Biological Oxidation-Reduction Reactions | |
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Oxidation of Hydroquinones/Reduction of Quinones | |
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More about Amines Heterocyclic Compounds | |
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More About Nomenclature | |
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More About Acid-Base Properties | |
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Amine Inversion | |
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Synthesis of Amines | |
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Reactions of Amines | |
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Reactions of Quaternary Ammonium Compounds | |
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Phase-Transfer Catalysis | |
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Unsaturated Five-Membered-Ring Heterocycles | |
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Unsaturated Six-Membered-Ring Heterocycles | |
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Biologically Important Heterocycles | |
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Carbohydrates | |
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Classification of Carbohydrates | |
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The D and L Notation | |
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Configurations of the Aldoses | |
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Configurations of the Ketoses | |
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Redox Reactions of Monosaccharides | |
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Osazone Formation | |
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Chain Elongation: The Kiliani-Fischer Synthesis | |
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Chain Shortening: The Ruff Degradation | |
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Stereochemistry of Glucose: The Fischer Proof | |
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Cyclic Structure of Monosaccharides: Hemiacetal Formation | |
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Stability of Glucose | |
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Acylation and Alkylation of Monosaccharides | |
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Formation of Glycosides | |
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The Anomeric Effect | |
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Reducing and Nonreducing Sugars | |
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Determination of Ring Size | |
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Disaccharides | |
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Polysaccharides | |
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Some Naturally Occurring Products Derived from Carbohydrates | |
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Carbohydrates on Cell Surfaces | |
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Synthetic Sweeteners | |
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Amino Acids, Peptides, and Proteins | |
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Classification and Nomenclature of Amino Acids | |
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Configuration of Amino Acids | |
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Acid-Base Properties of Amino Acids | |
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The Isoelectric Point | |
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Separation of Amino Acids | |
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Resolution of Racemic Mixtures of Amino Acids | |
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Peptide Bonds and Disulfide Bonds | |
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Some Interesting Peptides | |
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Strategy of Peptide Bond Synthesis: N-Protection and C-Activation | |
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Automated Peptide Synthesis | |
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Protein Structure | |
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Determining the Primary Structure of a Protein | |
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Secondary Structure of Proteins | |
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Tertiary Structure of Proteins | |
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Quaternary Structure of Proteins | |
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Protein Denaturation | |
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Catalysis | |
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Catalysis in Organic Reactions | |
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Nucleophilic Catalysis | |
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Acid Catalysis | |
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Base Catalysis | |
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Metal-Ion Catalysis | |
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Intramolecular Reactions | |
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Intramolecular Catalysis | |
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Catalysis in Biological Reactions | |
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Enzyme-Catalyzed Reactions | |
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Catalytic Antibodies and Artificial Enzymes | |
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The Organic Mechanisms of the Coenzymes Metabolism | |
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Overall View of Metabolism | |
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Niacin: The Vitamin Needed for Many Redox Reactions | |
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Flavin Adenine Dinucleotide and Flavin Mononucleotide: Vitamin B2 | |
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Thiamine Pyrophosphate: Vitamin B1 | |
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Biotin: Vitamin H | |
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Pyridoxal Phosphate: Vitamin B6 | |
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Coenzyme B12: Vitamin B12 | |
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Tetrahydrofolate: Folic Acid | |
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Vitamin KH2: Vitamin K | |
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Special Topics In Organic Chemistry | |
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Lipids | |
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Fatty Acids | |
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Waxes | |
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Fats and Oils | |
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Membranes | |
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Prostaglandins | |
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Terpenes | |
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Vitamin A | |
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Biosynthesis of Terpenes | |
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Steroids | |
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Biosynthesis of Cholesterol | |
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Synthetic Steroids | |
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Nucleosides, Nucleotides, and Nucleic Acids I | |
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Nucleosides and Nucleotides | |
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ATP: The Carrier of Chemical Energy | |
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Three Mechanisms for Phosphoryl Transfer Reactions | |
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The "High-Energy" Character of Phosphoanhydride Bonds | |
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Kinetic Stability of ATP in the Cell | |
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Other Important Nucleotides | |
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The Nucleic Acids | |
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Helical Forms of DNA | |
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Biosynthesis of DNA: Replication | |
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Biosynthesis of Messenger RNA: Transcription | |
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Ribosomal RNA | |
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Transfer RNA | |
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Biosynthesis of Proteins: Translation | |
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Why DNA Contains Thymine Instead of Uracil | |
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Determining the Base Sequence of DNA | |
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Laboratory Synthesis of DNA Strands | |
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Rational Drug Design | |
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Synthetic Polymers | |
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General Classes of Synthetic Polymers | |
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Chain-Growth Polymers | |
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Stereochemistry of Polymerization | |
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Ziegler-Natta Catalysts | |
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Polymerization of Dienes | |
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The Manufacture of Rubber | |
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Copolymers | |
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Step-Growth Polymers | |
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Physical Properties of Polymers | |
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Biodegradable Polymers | |
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Pericyclic Reactions | |
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Three Kinds of Pericyclic Reactions | |
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Molecular Orbitals and Orbital Symmetry | |
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Electrocyclic Reactions | |
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Cycloaddition Reactions | |
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Sigmatropic Rearrangements | |
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Pericyclic Reactions in Biological Systems | |
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Summary of the Selection Rules for Pericyclic Reactions | |
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The Organic Chemistry of Drugs: Discovery and Design | |
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Naming Drugs | |
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Lead Compounds | |
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Molecular Modification | |
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Random Screening | |
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Serendipity in Drug Development | |
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Receptors | |
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Drugs as Enzyme Inhibitors | |
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Designing a Suicide Substrate | |
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Quantitative Structure-Activity Relation-ships (QSAR) | |
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Molecular Modeling | |
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Combinatorial Organic Synthesis | |
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Antiviral Drugs | |
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Economics of Drugs | |
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Governmental Regulations | |
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Appendices | |
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Physical Properties of Organic Compounds | |
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Values | |
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Derivations of Rate Laws | |
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Summary of Methods Used to Synthesize a Particular Functional Group | |
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Summary of Methods Used to Form Carbon-Carbon Bonds | |
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Spectroscopy Tables | |
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Answers to Selected Problems | |
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Glossary | |
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Photo Credits | |