Efnisyfirlit

• Cover
• Half-Title
• Title
• Copyright
• Dedication
• Contents
• Preface to the Third Edition
• Common Abbreviations
• Videos to Accompany the Third Edition
• Scientist Photos and Acknowledgements
• Infrared Spectra Reprinted from SBDS
• Chapter 1 Introduction
• 1.1 A Brief History of Organic Chemistry
• 1.2 The Variety and Beauty of Organic Molecules
• Chapter 2 Why Is an Acid–Base Theme Important?
• 2.1 Traditional Acid and Base Theory
• 2.2 There are Two Acid-Base Definitions: How Are They Related?
• 2.3 Acid-Base Equilibria and Equilibrium Constants
• 2.4 Electronegativity and Atom Size
• 2.4.1 Electronegativity
• 2.4.2 Atom Size
• 2.5 Atom Size and Electronegativity Arguments Applied to Acids and Bases
• 2.6 Resonance, Electron Dispersion, and Base Strength
• 2.7 Lewis Acids and Bases
• 2.8 Why Is Acid–Base Chemistry a Theme for Organic Chemistry?
• 2.9 Biological Relevance
• Chapter 3 Bonding
• 3.1 Atomic Orbitals and Electrons
• 3.1.1 Atomic Orbitals
• 3.1.2 Electronic Configuration
• 3.2 Ionic versus Covalent Chemical Bonds
• 3.3 Covalent Bonds
• 3.4 Linear Combination of Atomic Orbital (LCAO) Model
• 3.5 Tetrahedral Carbons and sp3 Hybridization
• 3.5.1 The Experimentally Determined Structure of Methane
• 3.5.2 Electron Promotion and sp3 Hybridization
• 3.5.3 The Hybrid Carbon Model of sp3-Hybrid Orbitals
• 3.6 The Valence Shell Electron Pair Repulsion (VSEPR) Model
• 3.7 Breaking Covalent Bonds
• 3.8 Carbon Bonded to Heteroatoms
• 3.8.1 A Covalent Bond Between Carbon and a Heteroatom: Bond Polarization
• 3.8.2 Bond Polarity, Bond Moments, and Bond Strength
• Chapter 4 Alkanes, Isomers, and an Introduction to Nomenclature
• 4.1 Alkanes
• 4.2 Structural Variations of Alkane Hydrocarbons
• 4.2.1 Straight-Chain and Branched Alkanes
• 4.2.2 Isomers
• 4.3 The IUPAC Rules of Nomenclature
• 4.3.1 Prefixes and Simple Alkanes
• 4.3.2 Common Names
• 4.3.3 Halogens are Substituents
• 4.3.4 Multiple Substituents
• 4.3.5 Complex Substituents
• 4.4 Rings Made of Carbon: Cyclic Compounds
• 4.5 The Acid or Base Properties of Alkanes
• 4.6 Combustion Analysis and Empirical Formulas
• 4.7 Commercial and Biological Relevance
• Chapter 5 Functional Groups
• 5.1 π-Bonds. The C=C Unit and Alkenes
• 5.2 π-Bonds. The C≡C Unit and Alkynes
• 5.3 Hydrocarbons With Several π-Bonds
• 5.4 Terpenes
• 5.5 Heteroatom Functional Groups
• 5.5.1 Alcohols and Thiols
• 5.5.2 Ethers and Dithioethers (Sulfides)
• 5.5.3 Amines
• 5.6 Functional Groups with Polarized π-Bonds
• 5.6.1 The Carbonyl Functional Group, C=O
• 5.6.2 Aldehydes and Ketones
• 5.6.3 Carboxylic Acids, Carboxylic Anions, and Resonance
• 5.6.4 Double and Triple Bonds to Nitrogen
• 5.7 Acid-Base Properties of Functional Groups
• 5.8 Physical Properties and Intermolecular Forces
• 5.8.1 Boiling Point
• 5.8.2 Solubility
• 5.8.3 Melting Point
• 5.9 Benzene: A Special Cyclic Hydrocarbon
• 5.10 Biological Relevance
• Chapter 6 Acids, Bases, and Nucleophiles
• 6.1 Acid-Base Equilibria
• 6.2 Carboxylic Acids and Sulfonic Acids
• 6.2.1 Carboxylic Acids
• 6.2.2 Sulfonic Acids
• 6.3 Factors That Influence the Strength of a Carboxylic Acid
• 6.3.1 Stability of the Conjugate Base
• 6.3.2 Inductive Effects
• 6.3.3 Solvent Effects
• 6.4 Alcohols Are Amphoteric
• 6.5 Amines
• 6.6 Carbon Acids
• 6.6.1 Terminal Alkynes Are Weak Acids
• 6.6.2 α-Hydrogen Atoms and Carbonyls
• 6.7 Organic Bases
• 6.7.1 Amines
• 6.7.2 Alcohols Are Bases
• 6.7.3 Ethers Are Bases
• 6.7.4 Carbonyl Compounds Are Bases
• 6.7.5 Alkenes and Alkynes Are Bases
• 6.8 Lewis Acids and Lewis Bases
• 6.9 Nucleophiles
• 6.10 Biological Relevance
• Chapter 7 Chemical Reactions, Bond Energy, and Kinetics
• 7.1 A Chemical Reaction
• 7.2 Reactive Intermediates
• 7.3 Formal Charge
• 7.4 Free Energy: Enthalpy and Entropy
• 7.5 Bond Dissociation Enthalpy and Reactions
• 7.6 Transition States
• 7.7 Competing Reactions
• 7.8 Reversible Chemical Reactions
• 7.9 Reaction Curves and Intermediates
• 7.10 Mechanisms
• 7.11 Kinetics
• 7.11.1 Reaction Rate and First-Order Reactions
• 7.11.2 Second-Order Reactions
• 7.11.3 Half-Life
• 7.11.4 No Reaction
• 7.12 Biological Relevance
• Chapter 8 Conformations
• 8.1 Rotation Around C—C Bonds
• 8.1.1 Staggered and Eclipsed Rotamers
• 8.1.2 Torsional Strain: Steric Hindrance and Energy Barriers
• 8.2 Longer Chain Alkanes
• 8.3 Influence of Heteroatoms on the Rotamer Population
• 8.3.1 Halogen Substituents
• 8.3.2 OH or NH Groups in Alcohols or Amines
• 8.4 Introducing π-Bonds
• 8.5 Cyclic Alkanes
• 8.5.1 Strain and Steric Hindrance in Cyclic Alkanes
• 8.5.2 Conformations of C3–C5 Cycloalkanes
• 8.5.3 Conformationally Mobile Cyclohexane
• 8.6 Substituted Cyclohexanes. A1,3-Strain
• 8.7 Large Rings
• 8.8 Cyclic Alkenes
• 8.9 Biological Relevance
• Chapter 9 Stereoisomers: Chirality, Enantiomers, and Diastereomers
• 9.1 Stereogenic Carbons and Stereoisomers
• 9.2 Absolute Configuration [(R) and (S) Nomenclature]
• 9.3 Specific Rotation: A Physical Property
• 9.4 Circular Dichroism
• 9.5 Diastereomers
• 9.6 Alkenes
• 9.7 Cis and Trans Substituents Attached to Rings
• 9.8 Stereogenic Centers in Cyclic Molecules
• 9.9 Bicyclic Molecules
• 9.10 Optical Resolution
• 9.11 Biological Relevance
• Chapter 10 Acid-Base Reactions of π-Bonds: Addition Reactions
• 10.1 Carbocation Stability
• 10.2 Alkenes React with Brønsted-Lowry Acids
• 10.3 Carbocation Rearrangements
• 10.4 Hydration Reactions of Alkenes
• 10.5 Alkenes React with Dihalogens
• 10.5.1 Dihalogenation
• 10.5.3 Reaction With Aqueous Solutions of Halogens (Hypohalous Acids)
• 10.6 Alkenes React with Borane
• 10.7 Alkenes React With Mercury(II) Compounds
• 10.8 Alkynes React as Bases
• 10.8.1 Reaction with Brønsted-Lowry Acids
• 10.8.2 Hydration of Alkynes
• 10.8.3 Dihalogenation of Alkynes
• 10.8.4 Hydroboration of Alkynes
• 10.8.5 Oxymercuration of Alkynes
• 10.9 Metathesis
• 10.10 Non-Ionic Reactions. Radical Reactions
• 10.11 Polymerization
• 10.12 Organization of Reaction Types
• 10.13 Biological Relevance
• Chapter 11 Substitution Reactions
• 11.1 Alkyl Halides, Sulfonate Esters, and the Electrophilic C—X Bond
• 11.2 The SN2 Reaction
• 11.2.1 Nucleophilic Approach to an Electrophilic Carbon
• 11.2.2 Reaction Rate and Energy Requirements
• 11.2.3 The Role of the Solvent
• 11.3 Functional Group Transformations via the SN2 Reaction
• 11.4 The SN1 Reaction
• 11.5 Substitution Reactions of Alcohols
• 11.5.1 Alcohols React with Mineral Acids
• 11.5.2 Sulfur and Phosphorous Halide Reagents
• 11.5.3 The Mitsunobu Reaction
• 11.6 Reactions of Ethers
• 11.6.1 Ethers React as Brønsted-Lowry Bases
• 11.6.2 Reactions of Epoxides
• 11.7 Free Radical Halogenation of Alkanes
• 11.8 C—H Substitution
• 11.9 Organization of Reaction Types
• 11.10 Biological Relevance
• Chapter 12 Elimination and π–Bond-Forming Reactions
• 12.1 Bimolecular Elimination
• 12.2 Stereochemical Consequences of the E2 Reaction
• 12.3 The E2 Reaction in Cyclic Molecules
• 12.4 Unimolecular Elimination: The E1 Reaction
• 12.5 Intramolecular Elimination
• 12.6 Elimination Reactions of Vinyl Halides: Formation of Alkynes
• 12.7 Substitution versus Elimination
• 12.8 Strength and Limitations of the Simplifying Assumptions
• 12.9 Organization of Reaction Types
• 12.10 Biological Relevance
• Chapter 13 Spectroscopic Methods of Identification
• 13.1 Light and Energy
• 13.2 Mass Spectrometry
• 13.3 Infrared Spectroscopy
• 13.3.1 Absorbing Infrared Light and the Infrared Spectrophotometer
• 13.3.2 The Infrared Spectrum and Functional Group Absorptions
• 13.4 Nuclear Magnetic Resonance Spectroscopy
• 13.4.1 The Nuclear Magnetic Resonance Experiment
• 13.4.2 The Proton NMR Spectrum
• 13.5 Identifying Monofunctional Molecules
• 13.6 Carbon-13 NMR Spectroscopy: Counting the Carbons
• 13.7 Two-Dimensional (2D)-NMR
• 13.8 Biological Relevance
• Chapter 14 Organometallics
• 14.1 Organomagnesium Compounds
• 14.2 Grignard Reagents Are Bases and Nucleophiles
• 14.3 Organolithium Reagents
• 14.4 Organocuprates
• 14.5 Other Organometallic Compounds
• 14.6 Organization of Reaction Types
• 14.7 Biological Relevance
• Chapter 15 Oxidation
• 15.1 Defining an Oxidation
• 15.2 Oxidation of Alcohols
• 15.2.1 Chromium (VI) Oxidation of Alcohols
• 15.2.2 Swern Oxidation
• 15.3 Dihydroxylation of Alkenes
• 15.4 Epoxidation of Alkenes
• 15.5 Oxidative Cleavage
• 15.6 C—H Oxidation
• 15.7 Organization of Reaction Types
• 15.8 Biological Relevance
• Chapter 16 Reactions of Aldehydes and Ketones
• 16.1 Aldehydes and Ketones
• 16.2 The Reaction of Ketones and Aldehydes with Strong Nucleophiles
• 16.3 Stereoselectivity
• 16.4 The Reaction of Ketones and Aldehydes with Weak Nucleophiles
• 16.4.1 Reaction with Water
• 16.4.2 Reaction with Alcohols
• 16.4.3 Reaction With Amines
• 16.5 Organization of Reaction Types
• 16.6 Biological Relevance
• Chapter 17 Reduction
• 17.1 Defining a Reduction
• 17.2 Hydride Reducing Agents
• 17.3 Hydride Reduction of Other Functional Groups
• 17.4 Catalytic Hydrogenation
• 17.4.1 Hydrogenation of Alkenes and Alkynes
• 17.4.2 Homogenous Hydrogenation
• 17.4.3 Hydrogenation of Heteroatom Functional Groups
• 17.5 Dissolving Metal Reductions
• 17.6 Organization of Reaction Types
• 17.7 Biological Relevance
• Chapter 18 Carboxylic Acid Derivatives and Acyl Substitution
• 18.1 Carboxylic Acids
• 18.2 Carboxylic Acid Derivatives: Structure and Nomenclature
• 18.3 Sulfonic Acids and Derivatives
• 18.4 Acyl Substitution and Hydrolysis of Carboxylic Acid Derivatives
• 18.5 Preparation of Acid Chlorides and Acid Anhydrides
• 18.6 Preparation of Esters
• 18.7 Baeyer-Villiger Oxidation
• 18.8 Preparation of Amides
• 18.9 Carboxylic Acid Derivatives React with Carbon Nucleophiles
• 18.10 Dicarboxylic Acids and Derivatives
• 18.11 Nitrate Esters, Sulfate Esters, and Phosphate Esters
• 18.12 Nitriles Are Carboxylic Acid Derivatives
• 18.13 Fatty Acids and Lipids
• 18.14 Organization of Reaction Types
• 18.15 Biological Relevance
• Chapter 19 Aromatic Compounds and Benzene Derivatives
• 19.1 Benzene and Aromaticity
• 19.2 Substituted Benzene Derivatives
• 19.2.1 Alkyl Substituents (Arenes)
• 19.2.2 Functional Groups on the Benzene Ring
• 19.3 Electrophilic Aromatic Substitution
• 19.3.1 Aromatic Substitution: Halogenation, Nitration, and Sulfonation
• 19.3.2 Friedel–Crafts Alkylation
• 19.3.3 Friedel–Crafts Acylation
• 19.4 Disubstituted Benzene Derivatives
• 19.4.1 Regioselectivity
• 19.4.2 Activating and Deactivating Substituents
• 19.4.3 Halogen Substituents
• 19.4.4 Aniline and Aniline Derivatives
• 19.5 Polysubstituted Benzene Derivatives
• 19.6 Aromatic Coupling Reactions
• 19.7 Reduction and Aromatic Compounds
• 19.8 Aromaticity in Monocyclic Molecules Other Than Benzene
• 19.9 Polynuclear Aromatic Hydrocarbons
• 19.9.1 Naphthalene, Anthracene, and Phenanthrene
• 19.9.2 Aromatic Substitution Reactions of Polycyclic Hydrocarbons
• 19.10 Nucleophilic Aromatic Substitution
• 19.11 Aromatic Amines and Diazonium Salts
• 19.12 Benzyne Intermediates
• 19.13 Synthesis of Aromatic Compounds
• 19.14 Spectroscopy of Aromatic Compounds
• 19.15 Organization of Reaction Types
• 19.16 Biological Relevance
• Chapter 20 Enolate Anions: Acyl Addition and Acyl Substitution
• 20.1 Aldehydes and Ketones Are Weak Acids
• 20.1.1 Acidity of the α-Proton of Ketones and Aldehydes
• 20.2 Nonnucleophilic Bases
• 20.3 Enolate Alkylation
• 20.4 The Aldol Condensation
• 20.5 The Zimmerman-Traxler Model
• 20.6 The Intramolecular Aldol Condensation
• 20.7 The Acid-Catalyzed Aldol Condensation
• 20.8 Ester Enolate Anions
• 20.8.1 Alkylation of Ester Enolate Anions
• 20.8.2 Acyl Substitution and Acyl Addition
• 20.8.3 Intramolecular Condensation: The Dieckmann Condensation
• 20.8.4 Malonic Ester Enolate Anions
• 20.9 Decarboxylation
• 20.10 The Knoevenagel Reaction, the Malonic Ester Synthesis, and the Acetoacetic Acid Synthesis
• 20.11 Ylid Reactions
• 20.12 Organization of Reaction Types
• 20.13 Biological Relevance
• Chapter 21 Difunctional Molecules: Dienes and Conjugated Carbonyl Compounds
• 21.1 Conjugation
• 21.2 General Principles of Photochemistry
• 21.3 Detecting Conjugation with Spectroscopy
• 21.4 Reactions of Conjugated π-Bonds
• 21.5 Conjugate Addition
• 21.6 Reduction of Conjugate Systems
• 21.7 Organization of Reaction Types
• 21.8 Biological Relevance
• Chapter 22 Difunctional Molecules: Pericyclic Reactions
• 22.1 The Diels-Alder Reaction
• 22.2 Reactivity of Dienes and Alkenes
• 22.3 Selectivity in the Diels-Alder Reaction
• 22.4 Other Pericyclic Reactions
• 22.5 Sigmatropic Rearrangements
• 22.6 Organization of Reaction Types
• 22.7 Biological Relevance
• Chapter 23 Heteroaromatic Compounds
• 23.1 Nitrogen, Oxygen, and Sulfur in an Aromatic Ring
• 23.2 Substitution Reactions in Monocyclic Heterocyclic Aromatic Compounds
• 23.3 Heteroaromatic Compounds With More Than One Ring
• 23.4 Aromatic Substitution Reactions of Polycyclic Heterocycles
• 23.5 Reduced Heterocycles
• 23.6 Alkaloids
• 23.7 Biological Relevance
• Chapter 24 Multifunctional Compounds: Amines, Amino Acids and Peptides
• 24.1 Reactions That Form Amines
• 24.2 Amino Acids
• 24.3 Reactions and Synthesis of α-Amino Acids
• 24.4 Biological Relevance: Peptides
• 24.5 Biological Relevance: Proteins
• 24.6 Biological Relevance: Enzymes
• 24.7 Combinatorial Methods
• 24.8 Amino Acid Residue Identification in Proteins
• 24.9 End Group Analysis
• 24.10 Biological Relevance: Hormones
• Chapter 25 Multifunctional Compounds: Carbohydrates
• 25.1 Polyhydroxy Carbonyl Compounds
• 25.1.1 Monosaccharides
• 25.1.2 Hemi-Acetals
• 25.1.3 The Anomeric Effect
• 25.1.4 Ketose Monosaccharides
• 25.1.5 Amino Sugars
• 25.2 Disaccharides, Trisaccharides, Oligosaccharides, and Polysaccharides
• 25.3 Reactions of Carbohydrates
• 25.4 Glycans and Glycosides
• 25.5 Biological Relevance: Nucleosides and Nucleotides
• 25.6 Biological Relevance: Polynucleotides
• Index