Essential Organic Chemistry

Cover
Title Page
Copyright Page
Brief Table of Contents
Contents
Preface
About the Author
Chapter 1 Remembering General Chemistry: Electronic Structure and Bonding
	Natural Organic Compounds Versus Synthetic Organic Compounds
	1.1 The Structure of an Atom
	1.2 How the Electrons in an Atom Are Distributed
	1.3 Ionic and Covalent Bonds
	1.4 How the Structure of a Compound Is Represented
		PROBLEM-SOLVING STRATEGY
	1.5 Atomic Orbitals
	1.6 How Atoms Form Covalent Bonds
	1.7 How Single Bonds Are Formed in Organic Compounds
	1.8 How a Double Bond Is Formed: The Bonds in Ethene
	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
	Water-A Compound Central to Life
	1.13 The Bond in a Hydrogen Halide
	1.14 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
		PROBLEM-SOLVING STRATEGY
	1.15 The Dipole Moments of Molecules
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 2 Acids and Bases: Central to Understanding Organic Chemistry
	2.1 An Introduction to Acids and Bases
	2.2 pKa and pH
	Acid Rain
	2.3 Organic Acids and Bases
	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 pKa Value
	2.7 How Substituents Affect the Strength of an Acid
		PROBLEM-SOLVING STRATEGY
	2.8 An Introduction to Delocalized Electrons
	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
	Aspirin Must Be in Its Basic Form to Be Physiologically Active
	2.11 Buffer Solutions
	Blood: A Buffered Solution
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
	TUTORIAL Acids and Bases
Chapter 3 An Introduction to Organic Compounds
	3.1 How Alkyl Substituents Are Named
	Bad-Smelling Compounds
	3.2 The Nomenclature of Alkanes
	How is the Octane Number of Gasoline Determined?
	3.3 The Nomenclature of Cycloalkanes • Skeletal Structures
		PROBLEM-SOLVING STRATEGY
	3.4 The Nomenclature of Alkyl Halides
		PROBLEM-SOLVING STRATEGY
	3.5 The Classification of Alkyl Halides, Alcohols, and Amines
	Nitrosamines and Cancer
	3.6 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
	3.7 Noncovalent Interactions
		PROBLEM-SOLVING STRATEGY
	Drugs Bind to Their Receptors
	3.8 Factors that Affect the Solubility of Organic Compounds
	Cell Membranes
	3.9 Rotation Occurs About Carbon-Carbon Single Bonds
	3.10 Some Cycloalkanes have Angle Strain
	Von Baeyer, Barbituric Acid, and Blue Jeans
	3.11 Conformers of Cyclohexane
	3.12 Conformers of Monosubstituted Cyclohexanes
	Starch and Cellulose-Axial and Equatorial
	3.13 Conformers of Disubstituted Cyclohexanes
		PROBLEM-SOLVING STRATEGY
	3.14 Fused Cyclohexane Rings
	Cholesterol and Heart Disease
	How High Cholesterol Is Treated Clinically
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 4 Isomers: The Arrangement of Atoms in Space
	4.1 CIS-Trans Isomers Result from Restricted Rotation
	Cis-Trans Interconversion in Vision
	4.2 Designating Geometric Isomers Using the E,Z System
		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 How to Draw Enantiomers
	4.7 Naming Enantiomers by the R,S System
		PROBLEM-SOLVING STRATEGY
		PROBLEM-SOLVING STRATEGY
	4.8 Chiral Compounds Are Optically Active
	4.9 How Specific Rotation Is Measured
	4.10 Isomers with More than One Asymmetric Center
	4.11 Stereoisomers of Cyclic Compounds
		PROBLEM-SOLVING STRATEGY
	4.12 Meso Compounds Have Asymmetric Centers but Are Optically Inactive
		PROBLEM-SOLVING STRATEGY
	4.13 Receptors
	The Enantiomers of Thalidomide
	4.14 How Enantiomers Can Be Separated
	Chiral Drugs
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 5 Alkenes
	Pheromones
	5.1 The Nomenclature of Alkenes
	5.2 How an Organic Compound Reacts Depends on its Functional Group
	5.3 How Alkenes React . Curved Arrows Show the Flow of Electrons
	A Few Words About Curved Arrows
	5.4 Thermodynamics: How Much Product Is Formed?
	5.5 Increasing the Amount of Product Formed in a Reaction
	5.6 Using ΔH° Values to Determine the Relative Stabilities of Alkenes
		PROBLEM-SOLVING STRATEGY
	Trans Fats
	5.7 Kinetics: How Fast Is the Product Formed?
	5.8 The Rate of a Chemical Reaction
	5.9 The Reaction Coordinate Diagram for the Reaction of 2-Butene with HBr
	5.10 Catalysis
	5.11 Catalysis by Enzymes
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
	TUTORIAL An Exercise in Drawing Curved Arrows: Pushing Electrons
Chapter 6 The Reactions of Alkenes and Alkynes
	Green Chemistry: Aiming for Sustainability
	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 Electrophilic Addition Reactions Are Regioselective
	Which Are More Harmful, Natural Pesticides or Synthetic Pesticides?
		PROBLEM-SOLVING STRATEGY
	6.4 A Carbocation will Rearrange if It Can Form a More Stable Carbocation
	6.5 The Addition of Water to an Alkene
	6.6 The Stereochemistry of Alkene Reactions
		PROBLEM-SOLVING STRATEGY
	6.7 The Stereochemistry of Enzyme-Catalyzed Reactions
	6.8 Enantiomers Can Be Distinguished by Biological Molecules
	6.9 An Introduction to Alkynes
	Synthetic Alkynes Are Used to Treat Parkinson\'s Disease
	Why Are Drugs So Expensive?
	6.10 The Nomenclature of Alkynes
	Synthetic Alkynes Are Used for Birth Control
	6.11 The Structure of Alkynes
	6.12 The Physical Properties of Unsaturated Hydrocarbons
	6.13 The Addition of a Hydrogen Halide to an Alkyne
	6.14 The Addition of Water to an Alkyne
	6.15 The Addition of Hydrogen to an Alkyne
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 7 Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and the Reactions of Benzene
	7.1 Delocalized Electrons Explain Benzene\'s Structure
	Kekule\'s Dream
	7.2 The Bonding in Benzene
	7.3 Resonance Contributors and the Resonance Hybrid
	7.4 How to Draw Resonance Contributors
	Electron Delocalization Affects the Three-Dimensional Shape of Proteins
	7.5 The Predicted Stabilities of Resonance Contributors
	7.6 Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound
	7.7 Delocalized Electrons Increase Stability
		PROBLEM-SOLVING STRATEGY
		PROBLEM-SOLVING STRATEGY
	7.8 Delocalized Electrons Affect pKa Values
		PROBLEM-SOLVING STRATEGY
	7.9 Electronic Effects
	7.10 Delocalized Electrons Can Affect the Product of a Reaction
	7.11 Reactions of Dienes
	7.12 The Diels-Alder Reaction Is a 1, 4-Addition Reaction
	7.13 Benzene Is an Aromatic Compound
	7.14 The Two Criteria for Aromaticity
	7.15 Applying the Criteria for Aromaticity
	Buckyballs
	7.16 How Benzene Reacts
	7.17 The Mechanism for Electrophilic Aromatic Substitution Reactions
	Thyroxine
	7.18 Organizing What We Know About the Reactions of Organic Compounds
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
	TUTORIAL: DRAWING RESONANCE CONTRIBUTORS
Chapter 8 Substitution and Elimination Reactions of Alkyl Halides
	DDT: A Synthetic Organohalide That Kills Disease-Spreading Insects
	8.1 The Mechanism for an SN2 Reaction
	8.2 Factors That Affect SN2 Reactions
	Why Are Living Organisms Composed of Carbon Instead of Silicon?
	8.3 The Mechanism for an SN1 Reaction
	8.4 Factors That Affect SN1 Reactions
	8.5 Comparing SN2 and SN1 Reactions
		PROBLEM-SOLVING STRATEGY
	Naturally Occurring Organohalides That Defend against Predators
	8.6 Intermolecular versus Intramolecular Reactions
		PROBLEM-SOLVING STRATEGY
	8.7 Elimination Reactions of Alkyl Halides
	8.8 The Products of an Elimination Reaction
	8.9 Relative Reactivities of Alkyl Halides Reactions
	The Nobel Prize
	8.10 Does a Tertiary Alkyl Halide Undergo SN2/E2 Reactions or SN1/E1 Reactions?
	8.11 Competition between Substitution and Elimination
	8.12 Solvent Effects
	Solvation Efects
	8.13 Substitution Reactions in Synthesis
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 9 Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols
	9.1 The Nomenclature of Alcohols
	Grain Alcohol and Wood Alcohol
	9.2 Activating an Alcohol for Nucleophilic Substitution by Protonation
	9.3 Activating an OH Group for Nucleophilic Substitution in a Cell
	The Inability to Perform an SN2 Reaction Causes a Severe Clinical Disorder
	9.4 Elimination Reactions of Alcohols: Dehydration
	9.5 Oxidation of Alcohols
	Blood Alcohol Content
	Treating Alcoholism with Antabuse
	Methanol Poisoning
	9.6 Nomenclature of Ethers
	9.7 Nucleophilic Substitution Reactions of Ethers
	Anesthetics
	9.8 Nucleophilic Substitution Reactions of Epoxides
	9.9 Using Carbocation Stability to Determine the Carcinogenicity of an Arene Oxide
	Benzo[a]pyrene and Cancer
	Chimney Sweeps and Cancer
	9.10 Amines Do Not Undergo Substitution or Elimination Reactions
	Alkaloids
	Lead Compounds for the Development of Drugs
	9.11 Thiols, Sulfides, and Sulfonium Salts
	Mustard Gas-A Chemical Warfare Agent
	Alkylating Agents as Cancer Drugs
	9.12 Methylating Agents Used by Chemists versus Those Used by Cells
	Eradicating Termites
	S-Adenosylmethionine: A Natural Antidepressant
	9.13 Organizing What We Know about the Reactions of Organic Compounds
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 10 Determining the Structure of Organic Compounds
	10.1 Mass Spectrometry
	10.2 The Mass Spectrum • Fragmentation
	10.3 Using The m/z Value of The Molecular Ion to Calculate the Molecular Formula
		PROBLEM-SOLVING STRATEGY
	10.4 Isotopes in Mass Spectrometry
	10.5 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas
	10.6 Fragmentation Patterns
	10.7 Gas Chromatography-Mass Spectrometry
	Mass Spectrometry in Forensics
	10.8 Spectroscopy and the Electromagnetic Spectrum
	10.9 Infrared Spectroscopy
	10.10 Characteristic Infrared Absorption Bands
	10.11 The Intensity of Absorption Bands
	10.12 The Position of Absorption Bands
	10.13 The Position and Shape of an Absorption Band Is Affected by Electron Delocalization,
 Electron
 Donation and Withdrawal, and Hydrogen Bonding
		PROBLEM-SOLVING STRATEGY
	10.14 The Absence of Absorption Bands
	10.15 How to Interpret an Infrared Spectrum
	10.16 Ultraviolet and Visible Spectroscopy
	Ultraviolet Light and Sunscreens
	10.17 The Effect of Conjugation on Amax
	10.18 The Visible Spectrum and Color
	What Makes Blueberries Blue and Strawberries Red?
	10.19 Some Uses of UV/VIS Spectroscopy
	10.20 An Introduction to NMR Spectroscopy
	Nikola Tesla (1856-1943)
	10.21 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies
	10.22 The Number of Signals in an 1H NMR Spectrum
	10.23 The Chemical Shift Tells How Far the Signal Is from the Reference Signal
	10.24 The Relative Positions of 1H NMR Signals
	10.25 The Characteristic Values of Chemical Shifts
	10.26 The Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal
	10.27 The Splitting of Signals Is Described by the N + 1 Rule
	10.28 More Examples of 1H NMR Spectra
		PROBLEM-SOLVING STRATEGY
	10.29 13C NMR Spectroscopy
		PROBLEM-SOLVING STRATEGY
	NMR Used in Medicine is Called Magnetic Resonance Imaging
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 11 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
	11.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives
	Nature\'s Sleeping Pill
	11.2 The Structures of Carboxylic Acids and Carboxylic Acid Derivatives
	11.3 The Physical Properties of Carbonyl Compounds
	11.4 How Carboxylic Acids and Carboxylic Acid Derivatives React
		PROBLEM-SOLVING STRATEGY
	11.5 The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
	11.6 The Reactions of Acyl Chlorides
	11.7 The Reactions of Esters
	11.8 Acid-Catalyzed Ester Hydrolysis and Transesterification
	11.9 Hydroxide-Ion-Promoted Ester Hydrolysis
	Aspirin, NSAID s, and COX-2 Inhibitors
	11.10 Reactions of Carboxylic Acids
	11.11 Reactions of Amides
	Dalmatians: Do Not Fool with Mother Nature
	11.12 Acid-Catalyzed Amide Hydrolysis and Alcoholysis
	The Discovery of Penicillin
	Penicillin and Drug Resistance
	Penicillins in Clinical Use
	A Semisynthetic Penicillin
	11.13 Nitriles
	11.14 Acid Anhydrides
	What Drug-Enforcement Dogs Are Really Detecting
	11.15 How Chemists Activate Carboxylic Acids
	11.16 How Cells Activate Carboxylic Acids
	Nerve Impulses, Paralysis, and Insecticides
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 12 Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
	12.1 The Nomenclature of Aldehydes and Ketones
	Butanedione: An Unpleasant Compound
	12.2 The Relative Reactivities of Carbonyl Compounds
	12.3 How Aldehydes and Ketones React
	12.4 Organometallic Compounds
	12.5 The Reactions of Carbonyl Compounds with Grignard Reagents
	Synthesizing Organic Compounds
	Semisynthetic Drugs
		PROBLEM-SOLVING STRATEGY
	12.6 The Reactions of Aldehydes and Ketones with Cyanide Ion
	12.7 The Reactions of Carbonyl Compounds with Hydride Ion
	12.8 The Reactions of Aldehydes and Ketones with Amines
	Serendipity in Drug Development
	12.9 The Reactions of Aldehydes and Ketones with Alcohols
	Carbohydrates Form Hemiacetals and Acetals
	12.10 Nucleophilic Addition to a,B-Unsaturated Aldehydes and Ketones
	12.11 Nucleophilic Addition to a,B-Unsaturated Carboxylic Acid Derivatives
	Enzyme-Catalyzed Cis-Trans Interconversion
	12.12 Conjugate Addition Reactions in Biological Systems
	Cancer Chemotherapy
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 13 Reactions at the a-Carbon of Carbonyl Compounds
	13.1 The Acidity of an a-Hydrogen
		PROBLEM-SOLVING STRATEGY
	13.2 Keto-Enol Tautomers
	13.3 Keto-Enol Interconversion
	13.4 Alkylation of Enolate Ions
	The Synthesis of Aspirin
	13.5 An Aldol Addition Forms B-Hydroxyaldehydes or B-Hydroxyketones
	13.6 The Dehydration of Aldol Addition Products forms a,B-Unsaturated  Aldehydes and Ketones
	13.7 A Crossed Aldol Addition
	Breast Cancer and Aromatase Inhibitors
	13.8 A Claisen Condensation Forms a B-Keto Ester
	13.9 CO2 Can Be Removed from a Carboxylic Acid with a Carbonyl Group at the 3-Position
	13.10 Reactions at the a-Carbon in Cells
	13.11 Organizing What We Know about the Reactions of Organic Compounds
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 14 Radicals
	14.1 Alkanes are Unreactive Compounds
	Natural Gas and Petroleum
	Fossil Fuels: A Problematic Energy Source
	14.2 The Chlorination and Bromination of Alkanes
	Why Radicals No Longer Have to Be Called Free Radicals
	14.3 Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron
	14.4 The Distribution of Products Depends on Radical Stability
		PROBLEM-SOLVING STRATEGY
	14.5 The Stereochemistry of Radical Substitution Reactions
	14.6 Formation of Explosive Peroxides
	14.7 Radical Reactions Occur in Biological Systems
	Decaffeinated Coffee and the Cancer Scare
	Food Preservatives
	Is Chocolate a Health Food?
	14.8 Radicals and Stratospheric Ozone
	Artificial Blood
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 15 Synthetic Polymers
	15.1 There Are Two Major Classes of Synthetic Polymers
	15.2 Chain-Growth Polymers
	Teflon: An Accidental Discovery
	Recycling Symbols
	15.3 Stereochemistry of Polymerization • Ziegler-Natta Catalysts
	15.4 Organic Compounds That Conduct Electricity
	15.5 Polymerization of Dienes • Natural and Synthetic Rubber
	15.6 Copolymers
	Nanocontainers
	15.7 Step-Growth Polymers
	15.8 Classes of Step-Growth Polymers
	Health Con cerns: Bisphenol A and Phthalates
	Designing a Polymer
	15.9 Recycling Polymers
	15.10 Biodegradable Polymers
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 16 The Organic Chemistry of Carbohydrates
	16.1 Classification of Carbohydrates
	16.2 The D and L Notations
	16.3 The Configurations of Aldoses
	16.4 The Configurations of Ketoses
	16.5 The Reactions of Monosaccharides in Basic Solutions
	Measuring the Blood Glucose Levels in Diabetes
	16.6 Monosaccharides Form Cyclic Hemiacetals
	Vitamin C
	16.7 Glucose Is the Most Stable Aldohexose
	16.8 Formation of Glycosides
	16.9 Disaccharides
	Lactose Intolerance
	16.10 Polysaccharides
	Why the Dentist Is Right
	Heparin-A Natural Anticoagulant
	Controlling Fleas
	16.11 Carbohydrates on Cell Surfaces
	16.12 Artificial Sweeteners
	Acceptable Daily Intake
	SOME IMPORTANT THINGS TO REMEMBER
	SUMMARY OF REACTIONS
	PROBLEMS
Chapter 17 The Organic Chemistry of Amino Acids, Peptides, and Proteins
	17.1 The Nomenclature of Amino Acids
	Proteins and Nutrition
	17.2 The Configuration of Amino Acids
	Amino Acids and Disease
	17.3 The Acid-Base Properties of Amino Acids
	17.4 The Isoelectric Point
	17.5 Separating Amino Acids
	Water Softeners: Examples of Cation-Exchange Chromatography
	17.6 The Synthesis of Amino Acids
	17.7 The Resolution of Racemic Mixtures of Amino Acids
	17.8 Peptide Bonds and Disulfide Bonds
	Runner\'s High
	Diabetes
	Hair: Straight or Curly?
	17.9 An Introduction to Protein Structure
	Primary Structure and Taxonomic Relationship
	17.10 How to Determine the Primary Structure of a Polypeptide or a Protein
		PROBLEM-SOLVING STRATEGY
	17.11 Secondary Structure
	17.12 Tertiary Structure
	Diseases Caused by a Misfolded Protein
	17.13 Quaternary Structure
	17.14 Protein Denaturation
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 18 How Enzymes Catalyze Reactionss . The Organic Chemistry of the Vitamins available on-line
	18.1 Enzyme-Catalyzed Reactions
	18.2 An Enzyme-Catalyzed Reaction That Involves Two Sequential SN2 Reactions
	How Tamiflu Works
	18.3 An Enzyme-Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed Amide and Ester Hydrolysis
	18.4 An Enzyme-Catalyzed Reaction That Is Reminiscent of the Base-Catalyzed Enediol Rearrangement
	18.5 An Enzyme-Catalyzed Reaction That Is Reminiscent of a Retro-Aldol Addition
	18.6 Vitamins and Coenzymes
	Vitamin B1
	18.7 Niacin: The Vitamin Needed for Many Redox Reactions
	Niacin Deficiency
	18.8 Riboflavin: Another Vitamin Used in Redox Reactions
	18.9 Vitamin B1: The Vitamin Needed for Acyl Group Transfer
	Curing a Hangover with Vitamin B1
	18.10 Vitamin H: The Vitamin Needed for Carboxylation of an a-Carbon
		PROBLEM-SOLVING STRATEGY
	18.11 Vitamin B6: The Vitamin Needed for Amino Acid Transformations
	Assessing the Damage After a Heart Attack
	18.12 Vitamin B12: The Vitamin Needed for Certain Isomerizations
	18.13 Folic Acid: The Vitamin Needed for One-Carbon Transfer
	The First Antibiotics
	Competitive Inhibitors
	Cancer Drugs and Side Efects
	18.14 Vitamin K: The Vitamin Needed for Carboxylation of Glutamate
	Anticoagulants
	Too Much Broccoli
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 19 The Organic Chemistry of the Metabolic Pathways
	Differences in Metabolism
	19.1 ATP Is Used for Phosphoryl Transfer Reactions
	Why Did Nature Choose Phosphates?
	19.2 The \"High-Energy\" Character of Phosphoanhydride Bonds
	19.3 The Four Stages of Catabolism
	19.4 The Catabolism of Fats
	19.5 The Catabolism of Carbohydrates
		PROBLEM-SOLVING STRATEGY
	19.6 The Fate of Pyruvate
	19.7 The Catabolism of Proteins
	Phenylketonuria (PKU): An Inborn Error of Metabolism
	19.8 The Citric Acid Cycle
	19.9 Oxidative Phosphorylation
	Basal Metabolic Rate
	19.10 Anabolism
	19.11 Gluconeogenesis
	19.12 Regulating Metabolic Pathways
	19.13 Amino Acid Biosynthesis
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 20 The Organic Chemistry of Lipids
	20.1 Fatty Acids Are Long-Chain Carboxylic Acids
	Omega Fatty Acids
	Waxes Are Esters That Have High Molecular Weights
	20.2 Fats and Oils Are Triglycerides
	Whales and Echolocation
	20.3 Soaps and Detergents
	20.4 Phosphoglycerides and Sphingolipids
	Snake Venom
	Multiple Sclerosis and the Myelin Sheath
	20.5 Prostaglandins Regulate Physiological Responses
	20.6 Terpenes Contain Carbon Atoms in Multiples of Five
	20.7 How Terpenes are Biosynthesized
		PROBLEM-SOLVING STRATEGY
	20.8 How Nature Synthesizes Cholesterol
	20.9 Synthetic Steroids
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Chapter 21 The Chemistry of the Nucleic Acids
	21.1 Nucleosides and Nucleotides
	The Structure of DNA: Watson, Crick, Franklin, and Wilkins
	21.2 Nucleic Acids Are Composed of Nucleotide Subunits
	21.3 The Secondary Structure of DNA-The Double Helix
	21.4 Why DNA Does Not Have a 2\'-OH Group
	21.5 The Biosynthesis of DNA Is Called Replication
	21.6 DNA and Heredity
	Natural Products That Modify DNA
	21.7 The Biosynthesis of RNA Is Called Transcription
	21.8 The RNAs Used for Protein Biosynthesis
	21.9 The Biosynthesis of Proteins Is Called Translation
	Sickle Cell Anemia
	Antibiotics That Act by Inhibiting Translation
	21.10 Why DNA Contains Thymine Instead of Uracil
	Antibiotics Act by a Common Mechanism
	21.11 Antiviral Drugs
	Influenza Pandemics
	21.12 How the Base Sequence of DNA Is Determined
	21.13 Genetic Engineering
	Resisting Herbicides
	Using Genetic Engineering to Treat the Ebola Virus
	SOME IMPORTANT THINGS TO REMEMBER
	PROBLEMS
Appendix I Physical Properties of Organic Compounds
Appendix II Spectroscopy Tables
Answers to Selected Problems
Glossary
Photo Credits
Index
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