Organic chemistry

Cover
Title Page
Copyright Page
Preface
ACKNOWLEDGMENTS
About the Author
Contents
PART ONE: An Introduction to the Study of Organic Chemistry
	1 Remembering General Chemistry: Electronic Structure and Bonding
	CHEMICAL CONNECTION: Natural versus Synthetic Organic Compounds
		1.1 The Structure of an Atom
		1.2 How the Electrons in an Atom are Distributed
		1.3 Covalent Bonds
		1.4 How the Structure of a Compound is Represented
			PROBLEM-SOLVING STRATEGY
		1.5 Atomic Orbitals
		1.6 An Introduction to Molecular Orbital Theory
		1.7 How Single Bonds are Formed in Organic Compounds
		1.8 How a Double Bond is Formed: The Bonds in Ethene
			CHEMICAL CONNECTION: Diamond, Graphite, Graphene, and Fullerenes: Substances that Contain Only Carbon Atoms
		1.9 How a Triple Bond is Formed: The Bonds in Ethyne
		1.10 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion
		1.11 The Bonds in Ammonia and in the Ammonium Ion
		1.12 The Bonds in Water
			CHEMICAL CONNECTION: Water—A Unique Compound
		1.13 The Bond in a Hydrogen Halide
		1.14 Hybridization and Molecular Geometry
			PROBLEM-SOLVING STRATEGY
		1.15 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
			PROBLEM-SOLVING STRATEGY
		1.16 Dipole Moments of Molecules
			ESSENTIAL CONCEPTS
			PROBLEMS
	2 Acids and Bases: Central to Understanding Organic Chemistry
		2.1 An Introduction to Acids and Bases
		2.2 pK[Sub(a)] and pH
			PROBLEM-SOLVING STRATEGY
			CHEMICAL CONNECTION: Acid Rain
		2.3 Organic Acids and Bases
			BIOLOGICAL CONNECTION: Poisonous Amines
			PROBLEM-SOLVING STRATEGY
		2.4 How to Predict the Outcome of an Acid-Base Reaction
		2.5 How to Determine the Position of Equilibrium
		2.6 How the Structure of an Acid Affects its pK[Sub(a)] Value
		2.7 How Substituents Affect the Strength of an Acid
			PROBLEM-SOLVING STRATEGY
		2.8 An Introduction to Delocalized Electrons
			PROBLEM-SOLVING STRATEGY
			MEDICAL CONNECTION: Fosamax Prevents Bones from Being Nibbled Away
		2.9 A Summary of the Factors that Determine Acid Strength
		2.10 How pH Affects the Structure of an Organic Compound
			PROBLEM-SOLVING STRATEGY
			CHEMICAL CONNECTION: Derivation of the Henderson-Hasselbalch Equation
			MEDICAL CONNECTION: Aspirin Must Be in its Basic Form to be Physiologically Active
		2.11 Buffer Solutions
			MEDICAL CONNECTION: Blood: A Buffered Solution
		2.12 Lewis Acids and Bases
			ESSENTIAL CONCEPTS
			PROBLEMS
	TUTORIAL Acids and Bases
	3 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure
		3.1 Alkyl Groups
		3.2 The Nomenclature of Alkanes
			INDUSTRIAL CONNECTION: How is the Octane Number of Gasoline Determined?
		3.3 The Nomenclature of Cycloalkanes
			PROBLEM-SOLVING STRATEGY
		3.4 The Nomenclature of Alkyl Halides
		3.5 The Nomenclature of Ethers
		3.6 The Nomenclature of Alcohols
		3.7 The Nomenclature of Amines
			CHEMICAL CONNECTION: Bad-Smelling Compounds
		3.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
		3.9 Noncovalent Interactions
			PROBLEM-SOLVING STRATEGY
			MEDICAL CONNECTION: Drugs Bind to Their Receptors
		3.10 The Solubility of Organic Compounds
			BIOLOGICAL CONNECTION: Cell Membranes
		3.11 Rotation Occurs about Carbon–Carbon Single Bonds
		3.12 Some Cycloalkanes Have Angle Strain
			CHEMICAL CONNECTION: Von Baeyer, Barbituric Acid, and Blue Jeans
			PROBLEM-SOLVING STRATEGY
		3.13 Conformers of Cyclohexane
		3.14 Conformers of Monosubstituted Cyclohexanes
			CHEMICAL CONNECTION: Starch and Cellulose—Axial and Equatorial
		3.15 Conformers of Disubstituted Cyclohexanes
			PROBLEM-SOLVING STRATEGY
			PROBLEM-SOLVING STRATEGY
		3.16 Fused Cyclohexane Rings
			MEDICAL CONNECTION: Cholesterol and Heart Disease
			MEDICAL CONNECTION: How High Cholesterol is Treated Clinically
			ESSENTIAL CONCEPTS
			PROBLEMS
PART TWO: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization
	TUTORIAL Using Molecular Models
	4 Isomers: The Arrangement of Atoms in Space
		4.1 Cis–Trans Isomers Result from Restricted Rotation
			CHEMICAL CONNECTION: Cis-Trans Interconversion in Vision
		4.2 Using the E,Z System to Distinguish Isomers
			PROBLEM-SOLVING STRATEGY
		4.3 A Chiral Object Has a Nonsuperimposable Mirror Image
		4.4 An Asymmetric Center is a Cause of Chirality in a Molecule
		4.5 Isomers with One Asymmetric Center
		4.6 Asymmetric Centers and Stereocenters
		4.7 How to Draw Enantiomers
		4.8 Naming Enantiomers by the R,S System
			PROBLEM-SOLVING STRATEGY
			PROBLEM-SOLVING STRATEGY
		4.9 Chiral Compounds Are Optically Active
		4.10 How Specific Rotation Is Measured
		4.11 Enantiomeric Excess
		4.12 Compounds with More than One Asymmetric Center
		4.13 Stereoisomers of Cyclic Compounds
			PROBLEM-SOLVING STRATEGY
		4.14 Meso Compounds Have Asymmetric Centers but Are Optically Inactive
			PROBLEM-SOLVING STRATEGY
		4.15 How to Name Isomers with More than One Asymmetric Center
			PROBLEM-SOLVING STRATEGY
		4.16 Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
		4.17 Receptors
			MEDICAL CONNECTION: The Enantiomers of Thalidomide
		4.18 How Enantiomers Can Be Separated
			PHARMACEUTICAL CONNECTION: Chiral Drugs
			ESSENTIAL CONCEPTS
			PROBLEMS
	TUTORIAL Interconverting Structural Representations
	5 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics
	ENVIRONMENTAL CONNECTION: Pheromones
		5.1 Molecular Formulas and the Degree of Unsaturation
		5.2 The Nomenclature of Alkenes
		5.3 The Structure of Alkenes
			PROBLEM-SOLVING STRATEGY
		5.4 How An Organic Compound Reacts Depends on Its Functional Group
		5.5 How Alkenes React • Curved Arrows Show the Flow of Electrons
			GENERAL CONNECTION: A Few Words About Curved Arrows
		5.6 Thermodynamics: How Much Product is Formed?
		5.7 Increasing the Amount of Product Formed in a Reaction
		5.8 Calculating Δ H° Values
		5.9 Using Δ H° Values to Determine the Relative Stabilities of Alkenes
			PROBLEM-SOLVING STRATEGY
			NUTRITIONAL CONNECTION: Trans Fats
		5.10 Kinetics: How Fast is the Product Formed?
		5.11 The Rate of a Chemical Reaction
			CHEMICAL CONNECTION: The Difference between 5.11 The Rate of a Chemical Reaction Δ G[Sup(‡)] and E[Sub(a)]
		5.12 A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a  Reaction
		5.13 Catalysis
		5.14 Catalysis by Enzymes
			ESSENTIAL CONCEPTS
			PROBLEMS
			CHEMICAL CONNECTION: Calculating Kinetic Parameters
	TUTORIAL Drawing Curved Arrows
	6 The Reactions of Alkenes • The Stereochemistry of Addition Reactions
		6.1 The Addition of a Hydrogen Halide to an Alkene
		6.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon
		6.3 What Does the Structure of the Transition State Look Like?
		6.4 Electrophilic Addition Reactions Are Regioselective
			PROBLEM-SOLVING STRATEGY
		6.5 The Addition of Water to an Alkene
		6.6 The Addition of an Alcohol to an Alkene
		6.7 A Carbocation Will Rearrange if It Can Form a More Stable Carbocation
		6.8 The Addition of Borane to an Alkene: Hydroboration–Oxidation
			CHEMICAL CONNECTION: Borane and Diborane
		6.9 The Addition of a Halogen to an Alkene
			PROBLEM-SOLVING STRATEGY
		6.10 The Addition of a Peroxyacid to an Alkene
		6.11 The Addition of Ozone to an Alkene: Ozonolysis
			PROBLEM-SOLVING STRATEGY
		6.12 Regioselective, Stereoselective, And Stereospecific Reactions
		6.13 The Stereochemistry of Electrophilic Addition Reactions
			CHEMICAL CONNECTION: Cyclic Alkenes
			PROBLEM-SOLVING STRATEGY
		6.14 The Stereochemistry of Enzyme-Catalyzed Reactions
		6.15 Enantiomers Can Be Distinguished by Biological Molecules
			CHEMICAL CONNECTION: Chiral Catalysts
		6.16 Reactions and Synthesis
			ENVIRONMENTAL CONNECTION: Which are More Harmful: Natural Pesticides or Synthetic Pesticides?
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	7 The Reactions of Alkynes • An Introduction to Multistep Synthesis
	MEDICAL CONNECTION: Synthetic Alkynes Are Used to Treat Parkinson's Disease
	PHARMACEUTICAL CONNECTION: Why Are Drugs so Expensive?
		7.1 The Nomenclature of Alkynes
			MEDICAL CONNECTION: Synthetic Alkynes Are Used for Birth Control
		7.2 How to Name a Compound That Has More than One Functional Group
		7.3 The Structure of Alkynes
			BIOLOGICAL CONNECTION: How a Banana Slug Knows What to Eat
		7.4 The Physical Properties of Unsaturated Hydrocarbons
		7.5 The Reactivity of Alkynes
		7.6 The Addition of Hydrogen Halides and the Addition of Halogens to an Alkyne
		7.7 The Addition of Water to an Alkyne
		7.8 The Addition of Borane to an Alkyne: Hydroboration–Oxidation
		7.9 The Addition of Hydrogen to an Alkyne
		7.10 A Hydrogen Bonded to an sp Carbon Is "Acidic"
			CHEMICAL CONNECTION: Sodium Amide and Sodium in Ammonia
			PROBLEM-SOLVING STRATEGY
		7.11 Synthesis Using Acetylide Ions
		7.12 DESIGNING A SYNTHESIS I: An Introduction to Multistep Synthesis
			ENVIRONMENTAL CONNECTION: Green Chemistry: Aiming for Sustainability
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	8 Delocalized Electrons: Their Effect on Stability, pK[Sub(a)] , and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene
		8.1 Delocalized Electrons Explain Benzene's Structure
			HISTORICAL CONNECTION: Kekule's Dream
		8.2 The Bonding in Benzene
		8.3 Resonance Contributors and the Resonance Hybrid
		8.4 How to Draw Resonance Contributors
			BIOLOGICAL CONNECTION: Electron Delocalization Affects the Three-Dimensional Shape of Proteins
		8.5 The Predicted Stabilities of Resonance Contributors
			PROBLEM-SOLVING STRATEGY
		8.6 Delocalization Energy is the Additional Stability Delocalized Electrons Give to a Compound
		8.7 Delocalized Electrons Increase Stability
			INDUSTRIAL CONNECTION: Organic Compounds That Conduct Electricity
		8.8 A Molecular Orbital Description of Stability
		8.9 Delocalized Electrons Affect pK[Sub(a)] Values
			PROBLEM-SOLVING STRATEGY
		8.10 Electronic Effects
		8.11 Delocalized Electrons Can Affect the Product of a Reaction
		8.12 Reactions of Dienes
		8.13 Thermodynamic Versus Kinetic Control
		8.14 The Diels–Alder Reaction is a 1,4-Addition Reaction
		8.15 Retrosynthetic Analysis of the Diels–Alder Reaction
		8.16 Benzene is an Aromatic Compound
		8.17 The Two Criteria for Aromaticity
		8.18 Applying the Criteria for Aromaticity
			CHEMICAL CONNECTION: Buckyballs
			PROBLEM-SOLVING STRATEGY
		8.19 A Molecular Orbital Description of Aromaticity
		8.20 Aromatic Heterocyclic Compounds
		8.21 How Benzene Reacts
		8.22 Organizing What We Know About the Reactions of Organic Compounds (Group I)
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	TUTORIAL Drawing Resonance Contributors
PART THREE: Substitution and Elimination Reactions
	9 Substitution and Elimination Reactions of Alkyl Halides
	ENVIRONMENTAL CONNECTION: The Birth of the Environmental Movement
		9.1 The S[Sub(N)]2 Reaction
		9.2 Factors That Affect S[Sub(N)]2 Reactions
			CHEMICAL CONNECTION: Why Are Living Organisms Composed of Carbon Instead of Silicon?
		9.3 The S[Sub(N)]1 Reaction
		9.4 Factors That Affect S[Sub(N)]1 Reactions
		9.5 Competition Between S[Sub(N)]2 and S[Sub(N)]1 Reactions
			PROBLEM-SOLVING STRATEGY
			BIOLOGICAL CONNECTION: Naturally Occurring Alkyl Halides That Defend Against Predators
		9.6 Elimination Reactions of Alkyl Halides
		9.7 The E2 Reaction
		9.8 The E1 Reaction
			PROBLEM-SOLVING STRATEGY
		9.9 Competition Between E2 and E1 Reactions
		9.10 E2 and E1 Reactions are Stereoselective
			PROBLEM-SOLVING STRATEGY
		9.11 Elimination from Substituted Cyclohexanes
		9.12 Predicting the Products of the Reaction of an Alkyl Halide with a Nucleophile/Base
		9.13 Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides
			PROBLEM-SOLVING STRATEGY
			PROBLEM-SOLVING STRATEGY
		9.14 Solvent Effects
			CHEMICAL CONNECTION: Solvation Effects
			ENVIRONMENTAL CONNECTION: Environmental Adaptation
		9.15 Substitution and Elimination Reactions in Synthesis
		9.16 Intermolecular Versus Intramolecular Reactions
			PROBLEM-SOLVING STRATEGY
		9.17 DESIGNING A SYNTHESIS II: Approaching the Problem
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	10 Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
		10.1 Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides
			CHEMICAL CONNECTION: The Lucas Test
			GENERAL CONNECTION: Grain Alcohol and Wood Alcohol
		10.2 Other Methods Used to Convert Alcohols into Alkyl Halides
		10.3 Converting an Alcohol Into a Sulfonate Ester
			Forming a Sulfonate Ester
		10.4 Elimination Reactions of Alcohols: Dehydration
			PROBLEM-SOLVING STRATEGY
			BIOLOGICAL CONNECTION: Biological Dehydrations
		10.5 Oxidation of Alcohols
			GENERAL CONNECTION: Blood Alcohol Concentration
			MEDICAL CONNECTION: Treating Alcoholism with Antabuse
			MEDICAL CONNECTION: Methanol Poisoning
		10.6 Nucleophilic Substitution Reactions of Ethers
			MEDICAL CONNECTION: Anesthetics
		10.7 Nucleophilic Substitution Reactions of Epoxides
			CHEMICAL CONNECTION: Crown Ethers—Another Example of Molecular Recognition
			CHEMICAL CONNECTION: Crown Ethers Can be Used to Catalyze SN[Sub(2)] Reactions
		10.8 Arene Oxides
			ENVIRONMENTAL CONNECTION: Benzo[a]pyrene and Cancer
			ENVIRONMENTAL CONNECTION: Chimney Sweeps and Cancer
		10.9 Amines Do Not Undergo Substitution or Elimination Reactions
			BIOLOGICAL CONNECTION: Alkaloids
			PHARMACEUTICAL CONNECTION: Lead Compounds for the Development of Drugs
		10.10 Quaternary Ammonium Hydroxides Undergo Elimination Reactions
		10.11 Thiols, Sulfides, and Sulfonium Ions
			HISTORICAL CONNECTION: Mustard Gas–A Chemical Warfare Agent
			MEDICAL CONNECTION: Alkylating Agents as Cancer Drugs
		10.12 Methylating Agents Used by Chemists versus Those Used by Cells
			CHEMICAL CONNECTION: Eradicating Termites
			MEDICAL CONNECTION: S-Adenosylmethionine: A Natural Antidepressant
		10.13 Organizing What We Know About the Reactions of Organic Compounds (Group II)
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	11 Organometallic Compounds
		11.1 Organolithium and Organomagnesium Compounds
		11.2 Transmetallation
		11.3 Organocuprates
		11.4 Palladium-Catalyzed Coupling Reactions
			PROBLEM-SOLVING STRATEGY
		11.5 Alkene Metathesis
			HISTORICAL CONNECTION: Grubbs, Schrock, Suzuki, and Heck Receive the Nobel Prize
			HISTORICAL CONNECTION: The Nobel Prize
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	12 Radicals
		12.1 Alkanes are Unreactive Compounds
			GENERAL CONNECTION: Natural Gas and Petroleum
			GENERAL CONNECTION: Fossil Fuels: A Problematic Energy Source
		12.2 The Chlorination and Bromination of Alkanes
			HISTORICAL CONNECTION: Why Radicals No Longer Have to Be Called Free Radicals
		12.3 Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron
		12.4 The Distribution of Products Depends on Probability and Reactivity
		12.5 The Reactivity–Selectivity Principle
			PROBLEM-SOLVING STRATEGY
		12.6 Formation of Explosive Peroxides
		12.7 The Addition of Radicals to an Alkene
		12.8 The Stereochemistry of Radical Substitution and Radical Addition Reactions
		12.9 Radical Substitution of Allylic and Benzylic Hydrogens
			CHEMICAL CONNECTION: Cyclopropane
		12.10 DESIGNING A SYNTHESIS III: More Practice with Multistep Synthesis
		12.11 Radical Reactions in Biological Systems
			NUTRITIONAL CONNECTION: Decaffeinated Coffee and the Cancer Scare
			NUTRITIONAL CONNECTION: Food Preservatives
			NUTRITIONAL CONNECTION: Is Chocolate a Health Food?
		12.12 Radicals and Stratospheric Ozone
			MEDICAL CONNECTION: Artificial Blood
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	TUTORIAL Drawing Curved Arrows in Radical Systems
PART FOUR: Identification of Organic Compounds
	13 Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy
		13.1 Mass Spectrometry
		13.2 The Mass Spectrum • Fragmentation
		13.3 Using The m/z Value of the Molecular Ion to Calculate the Molecular Formula
			PROBLEM-SOLVING STRATEGY
		13.4 Isotopes in Mass Spectrometry
		13.5 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas
		13.6 The Fragmentation Patterns of Functional Groups
		13.7 Other Ionization Methods
		13.8 Gas Chromatography–Mass Spectrometry
			GENERAL CONNECTION: Mass Spectrometry in Forensics
		13.9 Spectroscopy and the Electromagnetic Spectrum
		13.10 Infrared Spectroscopy
		13.11 Characteristic Infrared Absorption Bands
		13.12 The Intensity of Absorption Bands
		13.13 The Position of Absorption Bands
			GENERAL CONNECTION: The Originator of Hooke's Law
		13.14 The Position and Shape of an Absorption Band is Affected by Electron Delocalization and Hydrogen Bonding
			PROBLEM-SOLVING STRATEGY
		13.15 C-H Absorption Bands
		13.16 The Absence of Absorption Bands
		13.17 Some Vibrations are Infrared Inactive
		13.18 How to Interpret an Infrared Spectrum
		13.19 Ultraviolet and Visible Spectroscopy
			GENERAL CONNECTION: Ultraviolet Light and Sunscreens
		13.20 The Beer–Lambert Law
		13.21 The Effect of Conjugation on λ[Sub(max)]
		13.22 The Visible Spectrum and Color
			CHEMICAL CONNECTION: What Makes Blueberries Blue and Strawberries Red?
		13.23 Some Uses of UV/Vis Spectroscopy
			ESSENTIAL CONCEPTS
			PROBLEMS
	14 NMR Spectroscopy
		14.1 An Introduction to NMR Spectroscopy
			HISTORICAL CONNECTION: Nikola Tesla (1856–1943)
		14.2 Fourier Transform NMR
		14.3 Shielding Causes Different Nuclei to Show Signals at Different Frequencies
		14.4 The Number of Signals in an [Sup(1)]H NMR Spectrum
			PROBLEM-SOLVING STRATEGY
		14.5 The Chemical Shift Tells How Far the Signal Is from the Reference Signal
		14.6 The Relative Positions of [Sup(1)]H NMR Signals
		14.7 The Characteristic Values of Chemical Shifts
		14.8 Diamagnetic Anisotropy
		14.9 The Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal
		14.10 The Splitting of Signals Is Described by the N + 1 Rule
		14.11 What Causes Splitting?
		14.12 More Examples of [Sup(1)]H NMR Spectra
		14.13 Coupling Constants Identify Coupled Protons
			PROBLEM-SOLVING STRATEGY
		14.14 Splitting Diagrams Explain the Multiplicity of a Signal
		14.15 Enantiotopic and Diastereotopic Hydrogens
		14.16 The Time Dependence of NMR Spectroscopy
		14.17 Protons Bonded to Oxygen and Nitrogen
		14.18 The Use of Deuterium in [Sup(1)]H NMR Spectroscopy
		14.19 The Resolution of [Sup(1)]H NMR Spectra
		14.20 [Sup(13)]C NMR Spectroscopy
			PROBLEM-SOLVING STRATEGY
		14.21 Dept [Sup(13)]C NMR Spectra
		14.22 Two-Dimensional NMR Spectroscopy
		14.23 NMR Used in Medicine is Called Magnetic Resonance Imaging
		14.24 X-Ray Crystallography
			GENERAL CONNECTION: Structural Databases
			ESSENTIAL CONCEPTS
			PROBLEMS
PART FIVE: Carbonyl Compounds
	15 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
		15.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives
			MEDICAL CONNECTION: Nature's Sleeping Pill
		15.2 The Structures of Carboxylic Acids and Carboxylic Acid Derivatives
		15.3 The Physical Properties of Carbonyl Compounds
		15.4 How Carboxylic Acids and Carboxylic Acid Derivatives React
			PROBLEM-SOLVING STRATEGY
		15.5 The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
		15.6 Reactions of Acyl Chlorides
		15.7 Reactions of Esters
		15.8 Acid-Catalyzed Ester Hydrolysis and Transesterification
		15.9 Hydroxide-Ion-Promoted Ester Hydrolysis
			PHARMACEUTICAL CONNECTION: Aspirin, NSAIDs, and COX-2 Inhibitors
		15.10 Reactions of Carboxylic Acids
			PROBLEM-SOLVING STRATEGY
		15.11 Reactions of Amides
			BIOLOGICAL CONNECTION: Dalmatians: Do Not Fool with Mother Nature
		15.12 Acid-Catalyzed Amide Hydrolysis and Alcoholysis
			HISTORICAL CONNECTION: The Discovery of Penicillin
			MEDICAL CONNECTION: Penicillin and Drug Resistance
			PHARMACEUTICAL CONNECTION: Penicillins in Clinical Use
			BIOLOGICAL CONNECTION: A Semisynthetic Penicillin
		15.13 Hydroxide-Ion-Promoted Hydrolysis of Amides
			INDUSTRIAL CONNECTION: Synthetic Polymers
			MEDICAL CONNECTION: Dissolving Sutures
		15.14 Hydrolysis of an Imide: a Way to Synthesize a Primary Amine
		15.15 Nitriles
		15.16 Acid Anhydrides
			GENERAL CONNECTION: What Drug-Enforcement Dogs Are Really Detecting
		15.17 Dicarboxylic Acids
		15.18 How Chemists Activate Carboxylic Acids
		15.19 How Cells Activate Carboxylic Acids
			CHEMICAL CONNECTION: Nerve Impulses, Paralysis, and Insecticides
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	16 Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
		16.1 The Nomenclature of Aldehydes and Ketones
			GENERAL CONNECTION: Butanedione: An Unpleasant Compound
		16.2 The Relative Reactivities of Carbonyl Compounds
		16.3 How Aldehydes and Ketones React
		16.4 Reactions of Carbonyl Compounds with Carbon Nucleophiles
			CHEMICAL CONNECTION: Enzyme-Catalyzed Carbonyl Additions
			PROBLEM-SOLVING STRATEGY
		16.5 Reactions of Carbonyl Compounds with Hydride Ion
		16.6 More About Reduction Reactions
		16.7 Chemoselective Reactions
		16.8 Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles
			PHARMACEUTICAL CONNECTION: Serendipity in Drug Development
		16.9 Reactions of Aldehydes and Ketones with Oxygen Nucleophiles
			BIOLOGICAL CONNECTION: Preserving Biological Specimens
			CHEMICAL CONNECTION: Carbohydrates
			PROBLEM-SOLVING STRATEGY
		16.10 Protecting Groups
		16.11 Reactions of Aldehydes and Ketones with Sulfur Nucleophiles
		16.12 Reactions of Aldehydes and Ketones with a Peroxyacid
		16.13 The Wittig Reaction Forms an Alkene
			CHEMICAL CONNECTION: β-Carotene
		16.14 DESIGNING A SYNTHESIS IV: Disconnections, Synthons, and Synthetic Equivalents
			CHEMICAL CONNECTION: Synthesizing Organic Compounds
			PHARMACEUTICAL CONNECTION: Semisynthetic Drugs
		16.15 Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones
		16.16 Nucleophilic Addition to α,β-Unsaturated Carboxylic Acid Derivatives
			CHEMICAL CONNECTION: Enzyme-Catalyzed Cis-Trans Interconversion
		16.17 Conjugate Addition Reactions in Biological Systems
			MEDICAL CONNECTION: Cancer Chemotherapy
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	17 Reactions at the α-Carbon
		17.1 The Acidity of an α-Hydrogen
			PROBLEM-SOLVING STRATEGY
		17.2 Keto–Enol Tautomers
		17.3 Keto–Enol Interconversion
		17.4 Halogenation of the α-Carbon of Aldehydes and Ketones
		17.5 Halogenation of the α-Carbon of Carboxylic Acids
		17.6 Forming an Enolate Ion
		17.7 Alkylating the α-Carbon
			PROBLEM-SOLVING STRATEGY
			INDUSTRIAL CONNECTION: The Synthesis of Aspirin
		17.8 Alkylating and Acylating the α-Carbon Via an Enamine Intermediate
		17.9 Alkylating the β-Carbon
		17.10 An Aldol Addition Forms a β-Hydroxyaldehyde or a β-Hydroxyketone
		17.11 The Dehydration of Aldol Addition Products Forms α,β-Unsaturated Aldehydes and Ketones
		17.12 A Crossed Aldol Addition
			MEDICAL CONNECTION: Breast Cancer and Aromatase Inhibitors
		17.13 A Claisen Condensation Forms a β-Keto Ester
		17.14 Other Crossed Condensations
		17.15 Intramolecular Condensations and Intramolecular Aldol Additions
		17.16 The Robinson Annulation
			PROBLEM-SOLVING STRATEGY
		17.17 CO[Sub(2)] Can be Removed from a Carboxylic Acid that has a Carbonyl Group at the 3-Position
		17.18 The Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid
		17.19 The Acetoacetic Ester Synthesis: A Way to Synthesize a Methyl Ketone
		17.20 DESIGNING A SYNTHESIS V: Making New Carbon–Carbon Bonds
		17.21 Reactions at the α-Carbon in Living Systems
		17.22 Organizing What We Know About the Reactions of Organic Compounds (Group III)
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	TUTORIAL Synthesis and Retrosynthetic Analysis
PART SIX: Aromatic Compounds
	18 Reactions of Benzene and Substituted Benzenes
	GENERAL CONNECTION: Measuring Toxicity
		18.1 The Nomenclature of Monosubstituted Benzenes
			GENERAL CONNECTION: The Toxicity of Benzene
		18.2 The General Mechanism for Electrophilic Aromatic Substitution Reactions
		18.3 Halogenation of Benzene
			MEDICAL CONNECTION: Thyroxine
		18.4 Nitration of Benzene
		18.5 Sulfonation of Benzene
		18.6 Friedel–Crafts Acylation of Benzene
		18.7 Friedel–Crafts Alkylation of Benzene
			CHEMICAL CONNECTION: Incipient Primary Carbocations
			BIOLOGICAL CONNECTION: A Biological Friedel-Crafts Alkylation
		18.8 Alkylation of Benzene by Acylation–Reduction
		18.9 Using Coupling Reactions to Alkylate Benzene
		18.10 How Some Substituents on a Benzene Ring Can Be Chemically Changed
		18.11 The Nomenclature of Disubstituted and Polysubstituted Benzenes
		18.12 The Effect of Substituents on Reactivity
		18.13 The Effect of Substituents on Orientation
		18.14 The Ortho–Para Ratio
		18.15 Additional Considerations Regarding Substituent Effects
		18.16 DESIGNING A SYNTHESIS VI: The Synthesis of Monosubstituted and Disubstituted Benzenes
		18.17 The Synthesis of Trisubstituted Benzenes
		18.18 Synthesizing Substituted Benzenes Using Arenediazonium Salts
		18.19 Azobenzenes
			HISTORICAL CONNECTION: Discovery of the First Antibiotic
			PHARMACEUTICAL CONNECTION: Drug Safety
		18.20 The Mechanism for the Formation of a Diazonium Ion
			MEDICAL CONNECTION: A New Cancer-Fighting Drug
			NUTRITIONAL CONNECTION: Nitrosamines and Cancer
		18.21 Nucleophilic Aromatic Substitution
		18.22 DESIGNING A SYNTHESIS VII: The Synthesis of Cyclic Compounds
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	19 More About Amines • Reactions of Heterocyclic Compounds
		19.1 More About Nomenclature
		19.2 More About the Acid–Base Properties of Amines
			MEDICAL CONNECTION: Atropine
		19.3 Amines React as Bases and as Nucleophiles
		19.4 Synthesis of Amines
		19.5 Aromatic Five-Membered-Ring Heterocycles
			PROBLEM-SOLVING STRATEGY
		19.6 Aromatic Six-Membered-Ring Heterocycles
		19.7 Some Heterocyclic Amines Have Important Roles in Nature
			PHARMACEUTICAL CONNECTION: Searching for Drugs: An Antihistamine, a Nonsedating Antihistamine, and a Drug for Ulcers
			MEDICAL CONNECTION: Porphyrin, Bilirubin, and Jaundice
		19.8 Organizing What We Know About the Reactions of Organic Compounds (Group IV)
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
PART SEVEN: Bioorganic Compounds
	20 The Organic Chemistry of Carbohydrates
		20.1 Classifying Carbohydrates
		20.2 The D and L Notation
		20.3 The Configurations of Aldoses
		20.4 The Configurations of Ketoses
		20.5 The Reactions of Monosaccharides in Basic Solutions
		20.6 Oxidation–Reduction Reactions of Monosaccharides
		20.7 Lengthening the Chain: The Kiliani–Fischer Synthesis
		20.8 Shortening the Chain: The Wohl Degradation
			MEDICAL CONNECTION: Measuring the Blood Glucose Levels in Diabetes
		20.9 The Stereochemistry of Glucose: The Fischer Proof
			GENERAL CONNECTION: Glucose/Dextrose
		20.10 Monosaccharides Form Cyclic Hemiacetals
		20.11 Glucose is the Most Stable Aldohexose
		20.12 Formation of Glycosides
		20.13 The Anomeric Effect
		20.14 Reducing and Nonreducing Sugars
		20.15 Disaccharides
			NUTRITIONAL CONNECTION: Lactose Intolerance
			MEDICAL CONNECTION: Galactosemia
			BIOLOGICAL CONNECTION: A Toxic Disaccharid
		20.16 Polysaccharides
			MEDICAL CONNECTION: Why the Dentist is Right
			BIOLOGICAL CONNECTION: Controlling Fleas
		20.17 Some Naturally Occurring Compounds Derived from Carbohydrates
			MEDICAL CONNECTION: Resistance to Antibiotics
			MEDICAL CONNECTION: Heparin–A Natural Anticoagulant
			HISTORICAL CONNECTION: Vitamin C
		20.18 Carbohydrates on Cell Surfaces
		20.19 Artificial Sweeteners
			NUTRITIONAL CONNECTION: Acceptable Daily Intake
			ESSENTIAL CONCEPTS
			SUMMARY OF REACTIONS
			PROBLEMS
	21 Amino Acids, Peptides, and Proteins
		21.1 The Nomenclature of Amino Acids
			NUTRITIONAL CONNECTION: Proteins and Nutrition
		21.2 The Configuration of Amino Acids
			MEDICAL CONNECTION: Amino Acids and Disease
			PHARMACEUTICAL CONNECTION: A Peptide Antibiotic
		21.3 Acid–Base Properties of Amino Acids
		21.4 The Isoelectric Point
		21.5 Separating Amino Acids
			GENERAL CONNECTION: Water Softeners: Examples of Cation-Exchange Chromatography
		21.6 Synthesis of Amino Acids
		21.7 Resolution of Racemic Mixtures of Amino Acids
		21.8 Peptide Bonds and Disulfide Bonds
			MEDICAL CONNECTION: Diabetes
			CHEMICAL CONNECTION: Hair: Straight or Curly?
		21.9 Some Interesting Peptides
		21.10 The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation
		21.11 Automated Peptide Synthesis
		21.12 An Introduction to Protein Structure
			BIOLOGICAL CONNECTION: Primary Structure and Taxonomic Relationship
		21.13 How to Determine the Primary Structure of a Polypeptide or a Protein
			PROBLEM-SOLVING STRATEGY
		21.14 Secondary Structure
			CHEMICAL CONNECTION: Right-Handed and Left-Handed Helices
			CHEMICAL CONNECTION: β-Peptides: An Attempt to Improve on Nature
		21.15 Tertiary Structure
			MEDICAL CONNECTION: Diseases Caused by a Misfolded Protein
		21.16 Quaternary Structure
		21.17 Protein Denaturation
			ESSENTIAL CONCEPTS
			PROBLEMS
	22 Catalysis in Organic Reactions and in Enzymatic Reactions
		22.1 Catalysis in Organic Reactions
		22.2 Acid Catalysis
		22.3 Base Catalysis
		22.4 Nucleophilic Catalysis
		22.5 Metal-Ion Catalysis
		22.6 Intramolecular Reactions
		22.7 Intramolecular Catalysis
		22.8 Catalysis in Biological Reactions
		22.9 An Enzyme-Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed Amide Hydrolysis
		22.10 Another Enzyme-Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed Amide Hydrolysis
		22.11 An Enzyme-Catalyzed Reaction That Involves Two Sequential S[Sub(N)]2 Reactions
			MEDICAL CONNECTION: How Tamiflu Works
		22.12 An Enzyme-Catalyzed Reaction That Is Reminiscent of the Base-Catalyzed Enediol Rearrangement
		22.13 An Enzyme Catalyzed-Reaction That Is Reminiscent of a Retro-Aldol Addition
			ESSENTIAL CONCEPTS
			PROBLEMS
	23 The Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins
	HISTORICAL CONNECTION: Vitamin B[Sub(1)]
		23.1 Niacin: The Vitamin Needed for Many Redox Reactions
			HISTORICAL CONNECTION: Niacin Deficiency
		23.2 Riboflavin: Another Vitamin Used in Redox Reactions
		23.3 Vitamin B[Sub(1)] : The Vitamin Needed for Acyl Group Transfer
			GENERAL CONNECTION: Curing a Hangover with Vitamin B[Sub(1)]
		23.4 Biotin: The Vitamin Needed for Carboxylation of an α-Carbon
		23.5 Vitamin B[Sub(6)] : The Vitamin Needed for Amino Acid Transformations
			MEDICAL CONNECTION: Assessing the Damage After a Heart Attack
		23.6 Vitamin B[Sub(12)] : The Vitamin Needed for Certain Isomerizations
		23.7 Folic Acid: The Vitamin Needed for One-Carbon Transfer
			HISTORICAL CONNECTION: The First Antibiotics
			MEDICAL CONNECTION: Cancer Drugs and Side Effects
			BIOLOGICAL CONNECTION: Competitive Inhibitors
		23.8 Vitamin K: The Vitamin Needed for Carboxylation of Glutamate
			MEDICAL CONNECTION: Anticoagulants
			NUTRITIONAL CONNECTION: Too Much Broccoli
			ESSENTIAL CONCEPTS
			PROBLEMS
	24 The Organic Chemistry of the Metabolic Pathways
	NUTRITIONAL CONNECTION: Differences in Metabolism
		24.1 ATP is Used for Phosphoryl Transfer Reactions
			CHEMICAL CONNECTION: Why Did Nature Choose Phosphates?
		24.2 Why ATP is Kinetically Stable in a Cell
		24.3 The "High-Energy" Character of Phosphoanhydride Bonds
		24.4 The Four Stages of Catabolism
		24.5 The Catabolism of Fats: Stages 1 and 2
		24.6 The Catabolism of Carbohydrates: Stages 1 and 2
			PROBLEM-SOLVING STRATEGY
			NUTRITIONAL CONNECTION: Fats Versus Carbohydrates as a Source of Energy
		24.7 The Fate of Pyruvate
		24.8 The Catabolism of Proteins: Stages 1 and 2
			MEDICAL CONNECTION: Phenylketonuria (PKU): An Inborn Error of Metabolism
			MEDICAL CONNECTION: Alcaptonuria
		24.9 The Citric Acid Cycle: Stage 3
		24.10 Oxidative Phosphorylation: Stage 4
			NUTRITIONAL CONNECTION: Basal Metabolic Rate
		24.11 Anabolism
		24.12 Gluconeogenesis
		24.13 Regulating Metabolic Pathways
		24.14 Amino Acid Biosynthesis
			ESSENTIAL CONCEPTS
			PROBLEMS
	25 The Organic Chemistry of Lipids
		25.1 Fatty Acids Are Long-Chain Carboxylic Acids
			NUTRITIONAL CONNECTION: Omega Fatty Acids
		25.2 Waxes Are High-Molecular-Weight Esters
		25.3 Fats and Oils Are Triglycerides
			NUTRITIONAL CONNECTION: Olestra: Nonfat with Flavor
			BIOLOGICAL CONNECTION: Whales and Echolocation
		25.4 Soaps and Micelles
		25.5 Phospholipids Are Components of Cell Membranes
			BIOLOGICAL CONNECTION: Snake Venom
			MEDICAL CONNECTION: Multiple Sclerosis and the Myelin Sheath
		25.6 Prostaglandins Regulate Physiological Responses
		25.7 Terpenes Contain Carbon Atoms in Multiples of Five
		25.8 How Terpenes Are Biosynthesized
			MEDICAL CONNECTION: How Statins Lower Cholesterol Levels
			PROBLEM-SOLVING STRATEGY
			CHEMICAL CONNECTION: Protein Prenylation
		25.9 How Nature Synthesizes Cholesterol
		25.10 Steroids
			MEDICAL CONNECTION: One Drug—Two Effects
		25.11 Synthetic Steroids
			ESSENTIAL CONCEPTS
			PROBLEMS
	26 The Chemistry of the Nucleic Acids
		26.1 Nucleosides and Nucleotides
			HISTORICAL CONNECTION: The Structure of DNA: Watson, Crick, Franklin, and Wilkins
			BIOLOGICAL CONNECTION: Cyclic AMP
		26.2 Nucleic Acids Are Composed of Nucleotide Subunits
		26.3 The Secondary Structure of DNA
		26.4 Why DNA Does Not Have A 2'-OH Group
		26.5 The Biosynthesis of DNA Is Called Replication
		26.6 DNA and Heredity
			PHARMACEUTICAL CONNECTION: Natural Products That Modify DNA
		26.7 The Biosynthesis of RNA Is Called Transcription
			BIOLOGICAL CONNECTION: There Are More Than Four Bases in DNA
		26.8 The RNAs Used for Protein Biosynthesis
		26.9 The Biosynthesis of Proteins Is Called Translation
			MEDICAL CONNECTION: Sickle Cell Anemia
			MEDICAL CONNECTION: Antibiotics That Act by Inhibiting Translation
		26.10 Why DNA Contains Thymine Instead of Uracil
			MEDICAL CONNECTION: Antibiotics Act by a Common Mechanism
		26.11 Antiviral Drugs
			HISTORICAL CONNECTION: Influenza Pandemics
		26.12 How the Base Sequence of DNA Is Determined
		26.13 Genetic Engineering
			ENVIRONMENTAL CONNECTION: Resisting Herbicides
			PHARMACEUTICAL CONNECTION: Using Genetic Engineering to Treat the Ebola Virus
			ESSENTIAL CONCEPTS
			PROBLEMS
PART EIGHT: Special Topics in Organic Chemistry
	27 Synthetic Polymers
		27.1 There Are Two Major Classes of Synthetic Polymers
		27.2 An Introduction To Chain-Growth Polymers
		27.3 Radical Polymerization
			INDUSTRIAL CONNECTION: Teflon: An Accidental Discovery
			ENVIRONMENTAL CONNECTION: Recycling Symbols
		27.4 Cationic Polymerization
		27.5 Anionic Polymerization
		27.6 Ring-Opening Polymerizations
		27.7 Stereochemistry of Polymerization • Ziegler–Natta Catalysts
		27.8 Polymerization of Dienes
		27.9 Copolymers
			PHARMACEUTICAL CONNECTION: Nanocontainers
		27.10 An Introduction to Step-Growth Polymers
		27.11 Classes of Step-Growth Polymers
			MEDICAL CONNECTION: Health Concerns: Bisphenol A and Phthalates
			INDUSTRIAL CONNECTION: Designing a Polymer
		27.12 Physical Properties of Polymers
			NUTRITIONAL CONNECTION: Melamine Poisoning
		27.13 Recycling Polymers
		27.14 Biodegradable Polymers
			ESSENTIAL CONCEPTS
			PROBLEMS
	28 Pericyclic Reactions
		28.1 There Are Three Kinds of Pericyclic Reactions
		28.2 Molecular Orbitals and Orbital Symmetry
		28.3 Electrocyclic Reactions
		28.4 Cycloaddition Reactions
		28.5 Sigmatropic Rearrangements
		28.6 Pericyclic Reactions in Biological Systems
			CHEMICAL CONNECTION: Bioluminescence
			NUTRITIONAL CONNECTION: The Sunshine Vitamin
			NUTRITIONAL CONNECTION: Animals, Birds, Fish—And Vitamin D
		28.7 Summary of the Selection Rules for Pericyclic Reactions
			ESSENTIAL CONCEPTS
			PROBLEMS
Appendices
	I: PK[Sub(A)] VALUES
	II: KINETICS
	III: SUMMARY OF METHODS USED TO SYNTHESIZE A PARTICULAR FUNCTIONAL GROUP
	IV: SUMMARY OF METHODS EMPLOYED TO FORM CARBON-CARBON BONDS
	V: SPECTROSCOPY TABLES
	VI: PHYSICAL PROPERTIES OF ORGANIC COMPOUNDS
ANSWERS TO SELECTED PROBLEMS
GLOSSARY
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CREDITS
INDEX
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