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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 | |