Efnisyfirlit

• Chapter 1: Atoms and Molecules; Orbitals and Bonding
• 1.1: Preview
• 1.2: Atoms and Atomic Orbitals
• 1.3: Covalent Bonds and Lewis Structures
• 1.4: Formal Charges
• 1.5: Resonance Forms and the Curved Arrow Formalism
• 1.6: Hydrogen (H2): Molecular Orbitals
• 1.7: Bond Strength
• 1.8: An Introduction to Reactivity: Acids and Bases
• 1.9: Special Topic: Quantum Mechanics and Babies
• 1.10: Summary
• 1.11: Additional Problems
• Chapter 2: Alkanes
• 2.1: Preview
• 2.2: Hybrid Orbitals: Making a Model for Methane
• 2.3: The Methyl Group (CH3) and Methyl Compounds (CH3X)
• 2.4: The Methyl Cation (+CH3), Anion (-:CH3), and Radial (.CH3)
• 2.5: Ethane (C2H6), Ethyl Compounds (C2H5X), and Newman Projections
• 2.6: Structure Drawings
• 2.7: Propane (C3H8) and Propyl Compounds (C3H7X)
• 2.8: Butanes (C4H10), Butyl Compounds (C4H9X), and Comformational Analysis
• 2.9: Pentanes (C5H12) and Pentyl Compounds (C5H11X)
• 2.10: The Naming Conventions for Alkanes
• 2.11: Drawing Isomers
• 2.12: Cycloalkanes
• 2.13: Physical Properties of Alkanes and Cycloalkanes
• 2.14: Nuclear Magnetic Resonance Spectra of Alkanes
• 2.15: Acids and Bases Revisited: More Chemical Reactions
• 2.16: Special Topic: Alkanes as Biomolecules
• 2.17: Summary
• 2.18: Additional Problems
• Chapter 3: Alkenes and Alkynes
• 3.1: Preview
• 3.2: Alkenes: Structure and Bonding
• 3.3: Derivatives and Isomers of Alkenes
• 3.4: Nomenclature
• 3.5: The Cahn-Ingold-Prelog Priority System
• 3.6: Relative Stability of Alkenes: Heats of Formation
• 3.7: Double Bonds in Rings
• 3.8: Physical Properties of Alkenes
• 3.9: Alkynes: Structure and Bonding
• 3.10: Relative Stability of Alkynes: Heats of Formation
• 3.11: Derivatives and Isomers of Alkynes
• 3.12: Triple Bonds in Rings
• 3.13: Physical Properties of Alkynes
• 3.14: Acidity of Alkynes
• 3.15: Molecular Formulas and Degrees of Unsaturation
• 3.16: An Introduction to Addition Reactions of Alkenes and Alkynes
• 3.17: Mechanism of the Addition of Hydrogen Halides to Alkenes
• 3.18: The Energetics of the Addition Reaction: Energy Diagrams
• 3.19: The Regiochemistry of the Addition Reaction
• 3.20: A Catalyzed Addition to Alkenes: Hydration
• 3.21: Synthesis: A Beginning
• 3.22: Special Topic: Alkenes and Biology
• 3.23: Summary
• 3.24: Additional Problems
• Chapter 4: Stereochemistry
• 4.1: Preview
• 4.2: Chirality
• 4.3: The (R/S) Convention
• 4.4: Properties of Enantiomers: Physical Differences
• 4.5: The Physical Basis of Optical Activity
• 4.6: Properties of Enantiomers: Chemical Differences
• 4.7: Interconversion of Enantiomers by Rotation about a Single Bond: gauche-Butane
• 4.8: Properties of Diastereomers: Molecules Containing More than One Stereogenic Atom
• 4.9: Resolution, a Method of Separating Enantiomers from Each Other
• 4.10: Determination of Absolute Configuration [(R) or (S)]
• 4.11: Stereochemical Analysis of Ring Compounds (a Beginning)
• 4.12: Summary of Isomerism
• 4.13: Special Topic: Chirality without “Four Different Groups Attached to One Carbon”
• 4.14: Special Topic: Stereochemistry in the Real World: Thalidomide, the Consequences of Being Wrong
• 4.15: Summary
• 4.16: Additional Problems
• Chapter 5: Rings
• 5.1: Preview
• 5.2: Rings and Strain
• 5.3: Quantitative Evaluation of Strain Energy
• 5.4: Stereochemistry of Cyclohexane: Conformational Analysis
• 5.5: Monosubstituted Cyclohexanes
• 5.6: Disubstituted Ring Compounds
• 5.7: Bicyclic Compounds
• 5.8: Special Topic: Polycyclic Systems
• 5.9: Special Topic: Adamantanes in Materials and Biology
• 5.10: Summary
• 5.11: Additional Problems
• Chapter 6: Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers, Thiols, and Thioethers
• 6.1: Preview
• 6.2: Nomenclature of Substituted Alkanes
• 6.3: Structure of Substituted Alkanes
• 6.4: Properties of Substituted Alkanes
• 6.5: Solubility
• 6.6: Formation of Substituted Alkanes
• 6.7: A Reaction of Alkyl Halides: Synthesis of Alkanes
• 6.8: Special Topic: Sulfur Compounds
• 6.9: Special Topic: Crown Ethers
• 6.10: Summary
• 6.11: Additional Problems
• Chapter 7: Substitution Reactions: The SN2 and SN1 Reactions
• 7.1: Preview
• 7.2: Review of Lewis Acids and Bases
• 7.3: Reactions of Alkyl Halides: The Substitution Reaction
• 7.4: Equilibrium and Reaction Rates, Thermodynamics and Kinetics
• 7.5: Substitution, Nucleophilic, Bimolecular: The SN2 Reaction
• 7.6: The SN2 Reaction in Biochemistry
• 7.7: Substitution, Nucleophilic, Unimolecular: The SN1 Reaction
• 7.8: Summary and Overview of the SN2 and SN1 Reactions
• 7.9: What Can We Do with These Reactions? How to Do Organic Synthesis
• 7.10: Summary
• 7.11: Additional Problems
• Chapter 8: Elimination Reactions: The E1 and E2 Reactions
• 8.1: Preview
• 8.2: The Unimolecular Reaction: E1
• 8.3: The Bimolecular Elimination Reaction: E2
• 8.4: Transition States: Thermodynamics versus Kinetics
• 8.5: Rearrangements of Carbocations
• 8.6: Special Topic: Other Eliminations
• 8.7: Special Topic: Enzymes and Reaction Rates
• 8.8: Special Topic: Why Are Rearrangements of Carbocations Fast?
• 8.9: Summary
• 8.10: Additional Problems
• Chapter 9: Analytical Chemistry: Spectroscopy
• 9.1: Preview
• 9.2: Chromatography
• 9.3: Mass Spectrometry
• 9.4: Ultraviolet/Visible Spectroscopy
• 9.5: Infrared Spectroscopy
• 9.6: 1H Nuclear Magnetic Resonance Spectroscopy
• 9.7: NMR Measurements
• 9.8: Special Topic: More-Complicated NMR Spectra
• 9.9: 13C NMR Spectroscopy
• 9.10: Problem Solving: How to Use Spectroscopy to Determine Structure
• 9.11: Special Topic: Dynamic NMR
• 9.12: Summary
• 9.13: Additional Problems
• Chapter 10: Electrophilic Additions to Alkenes
• 10.1: Preview
• 10.2: Mechanism of the Electrophilic Addition of Hydrogen Halides to Alkenes – Hydrohalogenation
• 10.3: Effects of Resonance on Regiochemistry
• 10.4: Brief Review of Resonance
• 10.5: Resonance and the Stability of Carbocations
• 10.6: Inductive Effects on Electrophilic Addition Reactions
• 10.7: More on Rearrangements of Carbocations
• 10.8: Mechanism of the Electrophilic Addition of Acid and Water to Alkenes – Hydration
• 10.9: Mechanism of Dimerization and Polymerization of Alkenes
• 10.10: Mechanism of Hydroboration of Alkenes
• 10.11: Hydroboration in Synthesis: Alcohol Formation
• 10.12: Special Topic: Rearrangements in Biological Processes
• 10.13: Summary
• 10.14: Additional Problems
• Chapter 11: More Additions to p Bonds
• 11.1: Preview
• 11.2: Electrophilic Addition of X2: Halogenation
• 11.3: Electrophilic Addition of Mercury: Oxymercuration
• 11.4: Electrophilic Addition of Oxygen: Epoxidation
• 11.5: Special Topic: Additions of Carbenes – Cyclopropane Synthesis
• 11.6: Dipolar Addition: Ozonolysis and Dihydroxylation
• 11.7: Hydrohalogenation of Alkynes
• 11.8: Hydration of Alkynes
• 11.9: Hydroboration of Alkynes
• 11.10: Reduction by Addition of H2: Hydrogenation
• 11.11: Reduction of Alkynes by Sodium in Ammonia
• 11.12: Special Topic: Three-Membered Rings in Biochemistry
• 11.13: Summary
• 11.14: Additional Problems
• Chapter 12: Radical Reactions
• 12.1: Preview
• 12.2: Formation and Simple Reactions of Radicals
• 12.3: Structure and Stability of Radicals
• 12.4: Radical Addition to Alkenes
• 12.5: Other Radical Addition Reactions
• 12.6: Radical-Initiated Addition of HBr to Alkynes
• 12.7: Photohalogenation
• 12.8: Allylic Halogenation: Synthetically Useful Reactions
• 12.9: Special Topic: Rearrangements (and Non-rearrangements) of Radicals
• 12.10: Special Topic: Radicals in Our Bodies; Do Free Radicals Age Us?
• 12.11: Summary
• 12.12: Additional Problems
• Chapter 13: Dienes and the Allyl System: 2p Orbitals in Conjugation
• 13.1: Preview
• 13.2: Allenes
• 13.3: Related Systems: Ketenes and Cumulenes
• 13.4: Allenes as Intermediates in the Isomerization of Alkynes
• 13.5: Conjugated Dienes
• 13.6: The Physical Consequences of Conjugation
• 13.7: The Chemical Consequences of Conjugation: Additional Reactions of Conjugated Dienes
• 13.8: Thermodynamic and Kinetic Control of Addition Reactions
• 13.9: The Allyl System: Three Overlapping 2p Orbitals
• 13.10: The Diels-Adler Reaction of Conjugated Dienes
• 13.11: Special Topic: Biosynthesis of Terpenes
• 13.12: Special Topic: Steroid Biosynthesis
• 13.13: Summary
• 13.14: Additional Problems
• Chapter 14: Aromaticity
• 14.1: Preview
• 14.2: The Structure of Benzene
• 14.3: A Resonance Picture of Benzene
• 14.4: The Molecular Orbital Picture of Benzene
• 14.5: Quantitative Evaluations of Resonance Stabilization in Benzene
• 14.6: A Generalization of Aromaticity: Huckel’s 4n + 2 Rule
• 14.7: Substituted Benzenes
• 14.8: Physical Properties of Substituted Benzenes
• 14.9: Heterobenzenes and Other Heterocyclic Aromatic Compounds
• 14.10: Polycyclic Aromatic Compounds
• 14.11: Special Topic: The Bio-Downside, the Mechanism of Carcinogenesis by Polycyclic Aromatic Hydro
• 14.12: The Benzyl Group and Its Reactivity
• 14.13: Introduction to the Chemistry of Benzene
• 14.14: Summary
• 14.15: Additional Problems
• Chapter 15: Substitution Reactions of Aromatic Compounds
• 15.1: Preview
• 15.2: Hydrogenation of Aromatic Compounds
• 15.3: Electrophilic Aromatic Substitution Reactions
• 15.4: Substitution Reactions We Can Do Using Nitrobenzene
• 15.5: Electrophilic Aromatic Substitution of Heteroaromatic Compounds
• 15.6: Disubstituted Benzenes: Ortho, Meta, and Para Substitution
• 15.7: Synthesis of Polysubstituted Benzenes
• 15.8: Nucleophilic Aromatic Substitution
• 15.9: Special Topic: Benzyne
• 15.10: Special Topic: Diels-Alder Reactions
• 15.11: Special Topic: Stable Carbocations in “Superacid”
• 15.12: Special Topic: Biological Synthesis of Aromatic Rings; Phenylalanine
• 15.13: Summary
• 15.14: Additional Problems
• Chapter 16: Carbonyl Chemistry 1: Addition Reactions
• 16.1: Preview
• 16.2: Structure of the Carbon-Oxygen Double Bond
• 16.3: Nomenclature of Carbonyl Compounds
• 16.4: Physical Properties of Carbonyl Compounds
• 16.5: Spectroscopy of Carbonyl Compounds
• 16.6: Reactions of Carbonyl Compounds: Simple Reversible Additions
• 16.7: Equilibrium in Addition Reactions
• 16.8: Other Addition Reactions: Additions of Cyanide and Bisulfite
• 16.9: Addition Reactions Followed by Water Loss: Acetal Formation
• 16.10: Protecting Groups in Synthesis
• 16.11: Addition Reactions of Nitrogen Bases: Imine and Enamine Formation
• 16.12: Organometallic Reagents
• 16.13: Irreversible Addition Reactions: A General Synthesis of Alcohols
• 16.14: Oxidation of Alcohols to Carbonyl Compounds
• 16.15: Retrosynthetic Alcohol Synthesis
• 16.16: Oxidation of Thiols and Other Sulfur Compounds
• 16.17: The Wittig Reaction
• 16.18: Special Topic: Biological Oxidation
• 16.19: Summary
• 16.20: Additional Problems
• Chapter 17: Carboxylic Acids
• 17.1: Preview
• 17.2: Nomenclature and Properties of Carboxylic Acids
• 17.3: Structure of Carboxylic Acids
• 17.4: Infrared and Nuclear Magnetic Resonance Spectra of Carboxylic Acids
• 17.5: Acidity and Basicity of Carboxylic Acids
• 17.6: Syntheses of Carboxylic Acids
• 17.7: Reactions of Carboxylic Acids
• 17.18: Special Topic: Carboxylic Acids in Nature
• 17.9: Summary
• 17.10: Additional Problems
• Chapter 18: Derivatives of Carboxylic Acids: Acyl Compounds
• 18.1: Preview
• 18.2: Nomenclature
• 18.3: Physical Properties and Structures of Acyl Compounds
• 18.4: Acidity and Basicity of Acyl Compounds
• 18.5: Spectral Characteristics
• 18.6: Reactions of Acid Chlorides: Synthesis of Acyl Compounds
• 18.7: Reactions of Anhydrides
• 18.8: Reactions of Esters
• 18.9: Reactions of Amides
• 18.10: Reactions of Nitriles
• 18.11: Reactions of Ketenes
• 18.12: Special Topic: Other Synthetic Routes to Acid Derivatives
• 18.13: Special Topic: A Family of Concerted Rearrangements of Acyl Compounds
• 18.14: Summary
• 18.15: Additional Problems
• Chapter 19: Carbonyl Chemistry 2: Reactions at the a Position
• 19.1: Preview
• 19.2: Many Carbonyl Compounds Are Weak Bronsted Acids
• 19.3: Racemization of Enols and Enolates
• 19.4: Halogenation in the a Position
• 19.5: Alkylation in the a Position
• 19.6: Addition of Carbonyl Compounds to the a Position: The Aldol Condensation
• 19.7: Reactions Related to the Aldol Condensation
• 19.8: Addition of Acid Derivatives to the a Position: The Claisen Condensation
• 19.9: Variations on the Claisen Condensation
• 19.10: Special Topic: Forward and Reverse Claisen Condensations in Biology
• 19.11: Condensation Reactions in Combination
• 19.12: Special Topic: Alkylation of Dithianes
• 19.13: Special Topic: Amines in Condensation Reactions, the Mannich Reaction
• 19.14: Special Topic: Carbonyl Compounds without a Hydrogens
• 19.15: Special Topic: The Aldol Condensation in the Real World, an Introduction to Modern Synthesis
• 19.16: Summary
• 19.17: Additional Problems
• Chapter 20: Carbohydrates
• 20.1: Preview
• 20.2: Nomenclature and Structure of Carbohydrates
• 20.3: Formation of Carbohydrates
• 20.4: Reactions of Carbohydrates
• 20.5: Special Topic: The Fischer Determination of the Structure of D-Glucose (and the 15 Other Aldo
• 20.6: Special Topic: An Introduction to Disaccharides and Polysaccharides
• 20.7: Summary
• 20.8: Additional Problems
• Chapter 21: Special Topic: Bioorganic Chemistry
• 21.1: Preview
• 21.2: Lipids
• 21.3: Formation of Neutral and Acidic Biomolecules
• 21.4: Alkaloids
• 21.5: Formation of Basic Biomolecules: Amine Chemistry
• 21.6: Summary
• 21.7: Additional Problems
• Chapter 22: Special Topic: Amino Acids and Polyamino Acids (Peptides and Proteins)
• 22.1: Preview
• 22.2: Amino Acids
• 22.3: Reactions of Amino Acids
• 22.4: Peptide Chemistry
• 22.5: Nucleosides, Nucleotides, and Nucleic Acids
• 22.6: Summary
• 22.7: Additional Problems
• Chapter 23: Special Topic: Reactions Controlled by Orbital Symmetry
• 23.1: Preview
• 23.2: Concerted Reactions
• 23.3: Electrocyclic Reactions
• 23.4: Cycloaddition Reactions
• 23.5: Sigmatropic Shift Reactions
• 23.6: The Cope Rearrangement
• 23.7: A Molecule with a Fluxional Structure
• 23.8: How to Work Orbital Symmetry Problems
• 23.9: Summary
• 23.10: Additional Problems
• Chapter 24: Special Topic: Intramolecular Reactions and Neighboring Group Participation
• 24.1: Preview
• 24.2: Heteroatoms as Neighboring Groups
• 24.3: Neighboring p Systems
• 24.4: Single Bonds as Neighboring Groups
• 24.5: Coates’ Cation
• 24.6: Summary
• 24.7: Additional Problems
• Glossary
• Credits
• Index