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• Cover
• Title Page
• Dedication
• Copyright
• Preface
• Acknowledgments
• About the Authors
• To the Student
• CHAPTER 1: The Basics
• 1.1 Life and the Chemistry of Carbon Compounds—We Are Stardust
• 1.2 Atomic Structure
• 1.3 Chemical Bonds: The Octet Rule
• 1.4 How To Write Lewis Structures
• 1.5 Formal Charges and How To Calculate Them
• 1.6 Isomers: Different Compounds That Have the Same Molecular Formula
• 1.7 How To Write and Interpret Structural Formulas
• 1.8 Resonance Structures and Curved Arrows
• 1.9 Quantum Mechanics and Atomic Structure
• 1.10 Atomic Orbitals and Electron Configuration
• 1.11 Molecular Orbitals
• 1.12 The Structure of Methane and Ethane: sp3 Hybridization
• 1.13 The Structure of Ethene (Ethylene): sp2 Hybridization
• 1.14 The Structure of Ethyne (Acetylene): sp Hybridization
• 1.15 A Summary of Important Concepts That Come from Quantum Mechanics
• 1.16 How To Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model
• 1.17 Applications of Basic Principles
• Summary and Review Tools
• Key Terms and Concepts
• Problems
• CHAPTER 2: Families of Carbon Compounds
• 2.1 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds
• 2.2 Polar Covalent Bonds
• 2.3 Polar and Nonpolar Molecules
• 2.4 Functional Groups
• 2.5 Alkyl Halides or Haloalkanes
• 2.6 Alcohols and Phenols
• 2.7 Ethers
• 2.8 Amines
• 2.9 Aldehydes and Ketones
• 2.10 Carboxylic Acids, Esters, and Amides
• 2.11 Nitriles
• 2.12 Summary of Important Families of Organic Compounds
• 2.13 Physical Properties and Molecular Structure
• 2.14 Summary of Attractive Forces
• 2.15 Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups
• 2.16 Interpreting IR Spectra
• 2.17 How to Interpret an IR Spectrum without any Knowledge of the Structure
• 2.18 Applications of Basic Principles
• Summary and Review Tools
• Key Terms and Concepts
• Problems
• CHAPTER 3: Acids and Bases
• 3.1 Acid–Base Reactions
• 3.2 How To Use Curved Arrows in Illustrating Reactions
• 3.3 Lewis Acids and Bases
• 3.4 Carbocations and Carbanions
• 3.5 The Strength of Brønsted–Lowry Acids and Bases: Ka and pKa
• 3.6 How To Predict the Outcome of Acid–Base Reactions
• 3.7 Relationships between Structure and Acidity
• 3.8 Energy Changes
• 3.9 The Relationship between the Equilibrium Constant and the Standard Free-Energy Change, ∆G°
• 3.10 Acidity: Carboxylic Acids versus Alcohols
• 3.11 The Effect of the Solvent on Acidity
• 3.12 Organic Compounds as Bases
• 3.13 A Mechanism for an Organic Reaction
• 3.14 Acids and Bases in Nonaqueous Solutions
• 3.15 Acid–Base Reactions and the Synthesis of Deuterium- and Tritium-Labeled Compounds
• 3.16 Applications of Basic Principles
• Summary and Review Tools
• Problems
• CHAPTER 4: Nomenclature and Conformations of Alkanes and Cycloalkanes
• 4.1 Introduction to Alkanes and Cycloalkanes
• 4.2 Shapes of Alkanes
• 4.3 How To Name Alkanes, Alkyl Halides, and Alcohols: the IUPAC System
• 4.4 How to Name Cycloalkanes
• 4.5 How To Name Alkenes and Cycloalkenes
• 4.6 How To Name Alkynes
• 4.7 Physical Properties of Alkanes and Cycloalkanes
• 4.8 Sigma Bonds and Bond Rotation
• 4.9 Conformational Analysis of Butane
• 4.10 The Relative Stabilities of Cycloalkanes: Ring Strain
• 4.11 Conformations of Cyclohexane: The Chair and the Boat
• 4.12 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups
• 4.13 Disubstituted Cycloalkanes: Cis-Trans Isomerism
• 4.14 Bicyclic and Polycyclic Alkanes
• 4.15 Chemical Reactions of Alkanes
• 4.16 Synthesis of Alkanes and Cycloalkanes
• 4.17 How To Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency
• 4.18 Applications of Basic Principles
• Summary and Review Tools
• Problems
• SPECIAL TOPIC A: 13C NMR Spectroscopy—A Practical Introduction
• A.1 One Signal for Each Distinct Carbon
• A.2 Chemical Shift—Location of the Signal Depends on Electronic Environment
• A.3 How To Use 13C NMR to Elucidate Structure
• CHAPTER 5: Stereochemistry
• 5.1 Chirality and Stereochemistry
• 5.2 Isomerism: Constitutional Isomers and Stereoisomers
• 5.3 Enantiomers and Chiral Molecules
• 5.4 Chiral Centers and Chiral Molecules
• 5.5 More about the Biological Importance of Chirality
• 5.6 How To Test for Chirality: Planes of Symmetry
• 5.7 Naming Enantiomers: The R,S-System
• 5.8 Properties of Enantiomers: Optical Activity
• 5.9 Racemic Forms
• 5.10 The Synthesis of Chiral Molecules
• 5.11 Chiral Drugs
• 5.12 Molecules with More than One Chiral Center
• 5.13 Fischer Projection Formulas
• 5.14 Stereoisomerism of Cyclic Compounds
• 5.15 Relating Configurations through Reactions in Which No Bonds to the Chiral Center Are Broken
• 5.16 Separation of Enantiomers: Resolution
• 5.17 Compounds with Chiral Centers Other than Carbon
• 5.18 Chiral Molecules That Do Not Possess a Chiral Center
• Summary and Review Tools
• Problems
• CHAPTER 6: Nucleophilic Reactions
• 6.1 Alkyl Halides
• 6.2 Nucleophilic Substitution Reactions
• 6.3 Nucleophiles
• 6.4 Leaving Groups
• 6.5 Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction
• 6.6 A Mechanism for the SN2 Reaction
• 6.7 Transition State Theory: Free-Energy Diagrams
• 6.8 The Stereochemistry of SN2 Reactions
• 6.9 The Reaction of Tert-Butyl Chloride with Water: An SN1 Reaction
• 6.10 A Mechanism for the SN1 Reaction
• 6.11 Carbocations
• 6.12 The Stereochemistry of SN1 Reactions
• 6.13 Factors Affecting the Rates of SN1 and SN2 Reactions
• 6.14 Organic Synthesis: Functional Group Transformations Using SN2 Reactions
• Summary and Review Tools
• Problems
• CHAPTER 7: Alkenes and Alkynes I
• 7.1 Introduction
• 7.2 The (E)–(Z) System for Designating Alkene Diastereomers
• 7.3 Relative Stabilities of Alkenes
• 7.4 Cycloalkenes
• 7.5 Synthesis of Alkenes: Elimination Reactions
• 7.6 Dehydrohalogenation
• 7.7 The E2 Reaction
• 7.8 The E1 Reaction
• 7.9 Elimination and Substitution Reactions Compete With Each Other
• 7.10 Elimination of Alcohols: Acid-Catalyzed Dehydration
• 7.11 Carbocation Stability and the Occurrence of Molecular Rearrangements
• 7.12 The Acidity of Terminal Alkynes
• 7.13 Synthesis of Alkynes by Elimination Reactions
• 7.14 Terminal Alkynes Can Be Converted to Nucleophiles For Carbon–Carbon Bond Formation
• 7.15 Hydrogenation of Alkenes
• 7.16 Hydrogenation: The Function of the Catalyst
• 7.17 Hydrogenation of Alkynes
• 7.18 An Introduction to Organic Synthesis
• Summary and Review Tools
• Problems
• CHAPTER 8: Alkenes and Alkynes II
• 8.1 Addition Reactions of Alkenes
• 8.2 Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov’s Rule
• 8.3 Stereochemistry of the Ionic Addition to an Alkene
• 8.4 Addition of Water to Alkenes: Acid-Catalyzed Hydration
• 8.5 Alcohols from Alkenes through Oxymercuration–Demercuration: Markovnikov Addition
• 8.6 Alcohols from Alkenes through Hydroboration–Oxidation: Anti-Markovnikov Syn Hydration
• 8.7 Hydroboration: Synthesis of Alkylboranes
• 8.8 Oxidation and Hydrolysis of Alkylboranes
• 8.9 Summary of Alkene Hydration Methods
• 8.10 Protonolysis of Alkylboranes
• 8.11 Electrophilic Addition of Bromine and Chlorine to Alkenes
• 8.12 Stereospecific Reactions
• 8.13 Halohydrin Formation
• 8.14 Divalent Carbon Compounds: Carbenes
• 8.15 Oxidation of Alkenes: Syn 1,2-Dihydroxylation
• 8.16 Oxidative Cleavage of Alkenes
• 8.17 Electrophilic Addition of Bromine and Chlorine to Alkynes
• 8.18 Addition of Hydrogen Halides to Alkynes
• 8.19 Oxidative Cleavage of Alkynes
• 8.20 How to Plan a Synthesis: Some Approaches and Examples
• Summary and Review Tools
• Problems
• CHAPTER 9: Nuclear Magnetic Resonance and Mass Spectrometry
• 9.1 Introduction
• 9.2 Nuclear Magnetic Resonance (NMR) Spectroscopy
• 9.3 How To Interpret Proton NMR Spectra
• 9.4 Shielding and Deshielding of Protons: More about Chemical Shift
• 9.5 Chemical Shift Equivalent and Nonequivalent Protons
• 9.6 Spin–Spin Coupling: More about Signal Splitting and Nonequivalent or Equivalent Protons
• 9.7 Proton NMR Spectra and Rate Processes
• 9.8 Carbon-13 NMR Spectroscopy
• 9.9 An Introduction to Mass Spectrometry
• 9.10 Formation of Ions: Electron Impact Ionization
• 9.11 Depicting the Molecular Ion
• 9.12 Fragmentation
• 9.13 Isotopes in Mass Spectra
• 9.14 GC/MS Analysis
• 9.15 Mass Spectrometry of Biomolecules
• Summary and Review Tools
• Problems
• SPECIAL TOPIC B: NMR Theory, Instrumentation, and 2D Spectra
• B.1 Nuclear Spin: The Origin of the Signal
• B.2 Detecting the Signal: Fourier Transform NMR Spectrometers
• B.3 The Chemical Shift
• B.4 Shielding and Deshielding of Protons: Induced Magnetic Fields
• B.5 Splitting Tree Diagrams and the Origin of Signal Splitting
• B.6 Factors that May Complicate 1H NMR Analyses
• B.7 Two-Dimensional (2D) NMR Techniques
• CHAPTER 10: Radical Reactions
• 10.1 Introduction: How Radicals Form and How They React
• 10.2 Homolytic Bond Dissociation Energies (DH°)
• 10.3 Reactions of Alkanes with Halogens
• 10.4 Chlorination of Methane: Mechanism of Reaction
• 10.5 Halogenation of Higher Alkanes
• 10.6 The Geometry of Alkyl Radicals
• 10.7 Reactions That Generate Chiral Centers
• 10.8 Allylic Substitution and Allylic Radicals
• 10.9 Benzylic Substitution and Benzylic Radicals
• 10.10 Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide
• 10.11 Radical Polymerization of Alkenes: Chain-Growth Polymers
• 10.12 Other Important Radical Reactions
• Summary and Review Tools
• Problems
• SPECIAL TOPIC C: Chain-Growth Polymers
• C.1 Stereochemistry of Chain-Growth Polymerization
• CHAPTER 11: Alcohols and Ethers
• 11.1 Structure and Nomenclature
• 11.2 Physical Properties of Alcohols and Ethers
• 11.3 Important Alcohols and Ethers
• 11.4 Synthesis of Alcohols from Alkenes
• 11.5 Reactions of Alcohols
• 11.6 Alcohols as Acids
• 11.7 Conversion of Alcohols into Alkyl Halides
• 11.8 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides
• 11.9 Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl2
• 11.10 Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols
• 11.11 Dehydration of Alcohols with POCl3
• 11.12 Synthesis of Ethers
• 11.13 Reactions of Ethers
• 11.14 Epoxides
• 11.15 Reactions of Epoxides
• 11.16 Anti 1,2-Dihydroxylation of Alkenes via Epoxides
• 11.17 Crown Ethers
• 11.18 Summary of Reactions of Alkenes, Alcohols, and Ethers
• Summary and Review Tools
• Problems
• CHAPTER 12: Alcohols from Carbonyl Compounds
• 12.1 Structure of the Carbonyl Group
• 12.2 Oxidation–Reduction Reactions in Organic Chemistry
• 12.3 Alcohols by Reduction of Carbonyl Compounds
• 12.4 Oxidation of Alcohols
• 12.5 Organometallic Compounds
• 12.6 Preparation of Organolithium and Organomagnesium Compounds
• 12.7 Reactions of Organolithium and Organomagnesium Compounds
• 12.8 Alcohols from Grignard Reagents
• 12.9 Protecting Groups
• Summary and Review Tools
• Problems
• First Review Problem Set
• CHAPTER 13: Conjugated Unsaturated Systems
• 13.1 Introduction
• 13.2 The Stability of the Allyl Radical
• 13.3 The Allyl Cation
• 13.4 Resonance Theory Revisited
• 13.5 Alkadienes and Polyunsaturated Hydrocarbons
• 13.6 1,3-Butadiene: Electron Delocalization
• 13.7 The Stability of Conjugated Dienes
• 13.8 Ultraviolet–Visible Spectroscopy
• 13.9 Electrophilic Attack on Conjugated Dienes: 1,4-Addition
• 13.10 The Diels–Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes
• Summary and Review Tools
• Problems
• CHAPTER 14: Aromatic Compounds
• 14.1 The Discovery of Benzene
• 14.2 Nomenclature of Benzene Derivatives
• 14.3 Reactions of Benzene
• 14.4 The Kekulé Structure for Benzene
• 14.5 The Thermodynamic Stability of Benzene
• 14.6 Modern Theories of the Structure of Benzene
• 14.7 Hückel’s Rule: The 4n + 2 π Electron Rule
• 14.8 The Annulenes
• 14.9 NMR Spectroscopy: Evidence for Electron Delocalization in Aromatic Compounds
• 14.10 Aromatic Ions
• 14.11 Other Aromatic Compounds
• 14.12 Heterocyclic Aromatic Compounds
• 14.13 Aromatic Compounds in Biochemistry
• 14.14 Spectroscopy of Aromatic Compounds
• Summary and Review Tools
• Problems
• SPECIAL TOPIC D: Electrocyclic and Cycloaddition Reactions
• D.1 Introduction
• D.2 Electrocyclic Reactions
• D.3 The Cope and Claisen Rearrangements
• D.4 Cycloaddition Reactions
• CHAPTER 15: Reactions of Aromatic Compounds
• 15.1 Electrophilic Aromatic Substitution Reactions
• 15.2 A General Mechanism for Electrophilic Aromatic Substitution
• 15.3 Halogenation of Benzene
• 15.4 Nitration of Benzene
• 15.5 Sulfonation of Benzene
• 15.6 Friedel–Crafts Reactions
• 15.7 Synthetic Applications of Friedel–Crafts Acylations: The Clemmensen and Wolff–Kishner Reductions
• 15.8 Existing Substituents Direct the Position of Electrophilic Aromatic Substitution
• 15.9 Activating and Deactivating Effects: How Electron-Donating and Electron-Withdrawing Groups Affect the Rate of an EAS Reaction
• 15.10 Directing Effects in Disubstituted Benzenes
• 15.11 Reactions of Benzene Ring Carbon Side Chains
• 15.12 Synthetic Strategies
• 15.13 SNAr: Nucleophilic Aromatic Substitution
• 15.14 Benzyne: Nucleophilic Aromatic Substitution by Elimination–Addition
• 15.15 Reduction of Aromatic Compounds
• Summary and Review Tools
• Problems
• CHAPTER 16: Aldehydes and Ketones
• 16.1 Introduction
• 16.2 Nomenclature of Aldehydes and Ketones
• 16.3 Physical Properties
• 16.4 Synthesis of Aldehydes
• 16.5 Synthesis of Ketones
• 16.6 Nucleophilic Addition to the Carbon–Oxygen Double Bond: Mechanistic Themes
• 16.7 The Addition of Alcohols: Hemiacetals and Acetals
• 16.8 The Addition of Primary and Secondary Amines
• 16.9 The Addition of Hydrogen Cyanide: Cyanohydrins
• 16.10 The Addition of Ylides: The Wittig Reaction
• 16.11 Oxidation of Aldehydes
• 16.12 The Baeyer–Villiger Oxidation
• 16.13 Spectroscopic Properties of Aldehydes and Ketones
• 16.14 Summary of Aldehyde and Ketone Addition Reactions
• Summary and Review Tools
• Problems
• CHAPTER 17: Carboxylic Acids and Their Derivatives
• 17.1 Introduction
• 17.2 Nomenclature and Physical Properties
• 17.3 Preparation of Carboxylic Acids
• 17.4 Acyl Substitution: Nucleophilic Addition–Elimination at the Acyl Carbon
• 17.5 Acyl Chlorides
• 17.6 Carboxylic Acid Anhydrides
• 17.7 Esters
• 17.8 Amides
• 17.9 Derivatives of Carbonic Acid
• 17.10 Decarboxylation of Carboxylic Acids
• 17.11 Polyesters and Polyamides: Step-Growth Polymers
• 17.12 Summary of the Reactions of Carboxylic Acids and Their Derivatives
• Summary and Review Tools
• Problems
• SPECIAL TOPIC E: Step-Growth Polymers
• E.1 Polyamides
• E.2 Polyesters
• E.3 Polyurethanes
• E.4 Phenol–Formaldehyde Polymers
• CHAPTER 18: Reactions at the α Carbon of Carbonyl Compounds
• 18.1 The Acidity of the α Hydrogens of Carbonyl Compounds: Enolate Anions
• 18.2 Keto and Enol Tautomers
• 18.3 Reactions via Enols and Enolates
• 18.4 Lithium Enolates
• 18.5 Enolates of β-Dicarbonyl Compounds
• 18.6 Synthesis of Methyl Ketones Using Ethyl Acetoacetate: The Acetoacetic Ester Synthesis
• 18.7 Synthesis of Substituted Acetic Acids: The Malonic Ester Synthesis
• 18.8 Further Reactions of Active Hydrogen Compounds
• 18.9 Synthesis of Enamines: Stork Enamine Reactions
• 18.10 Summary of Enolate Chemistry
• Summary and Review Tools
• Problems
• CHAPTER 19: Condensation and Conjugate Addition Reactions of Carbonyl Compounds
• 19.1 Introduction
• 19.2 The Claisen Condensation: A Synthesis of β-Keto Esters
• 19.3 β-Dicarbonyl Compounds by Acylation of Ketone Enolates
• 19.4 Aldol Reactions: Addition of Enolates and Enols to Aldehydes and Ketones
• 19.5 Crossed Aldol Condensations
• 19.6 Cyclizations via Aldol Condensations
• 19.7 Additions to α,β-Unsaturated Aldehydes and Ketones
• 19.8 The Mannich Reaction
• 19.9 Summary of Important Reactions
• Summary and Review Tools
• Problems
• SPECIAL TOPIC F: Thiols, Sulfur Ylides, and Disulfides
• F.1 Preparation of Thiols
• F.2 Physical Properties of Thiols
• F.3 The Addition of Sulfur Ylides to Aldehydes and Ketones
• F.4 Thiols and Disulfides in Biochemistry
• SPECIAL TOPIC G: Thiol Esters and Lipid Biosynthesis
• G.1 Thiol Esters
• G.2 Biosynthesis of Fatty Acids
• G.3 Biosynthesis of Isoprenoid Compounds
• G.4 Biosynthesis of Steroids
• G.5 Cholesterol and Heart Disease
• CHAPTER 20: Amines
• 20.1 Nomenclature
• 20.2 Physical Properties and Structure of Amines
• 20.3 Basicity of Amines: Amine Salts
• 20.4 Preparation of Amines
• 20.5 Reactions of Amines
• 20.6 Reactions of Amines with Nitrous Acid
• 20.7 Replacement Reactions of Arenediazonium Salts
• 20.8 Coupling Reactions of Arenediazonium Salts
• 20.9 Reactions of Amines with Sulfonyl Chlorides
• 20.10 Synthesis of Sulfa Drugs
• 20.11 Analysis of Amines
• 20.12 Eliminations Involving Ammonium Compounds
• 20.13 Summary of Preparations and Reactions of Amines
• Summary and Review Tools
• Problems
• SPECIAL TOPIC H: Alkaloids
• H.1 Alkaloids Containing a Pyridine or Reduced Pyridine Ring
• H.2 Alkaloids Containing an Isoquinoline or Reduced Isoquinoline Ring
• H.3 Alkaloids Containing Indole or Reduced Indole Rings
• CHAPTER 21: Transition Metal Complexes
• 21.1 Organometallic Compounds in Previous Chapters
• 21.2 Transition Metal Elements and Complexes
• 21.3 How to Count Electrons in a Metal Complex
• 21.4 Mechanistic Steps in the Reactions of Some Transition Metal Complexes
• 21.5 Homogeneous Hydrogenation: Wilkinson’s Catalyst
• 21.6 Cross-Coupling Reactions
• 21.7 Olefin Metathesis
• 21.8 Transition Metals in Nature: Vitamin B12 and Vanadium Haloperoxidases
• Summary and Review Tools
• Problems
• Second Review Problem Set
• CHAPTER 22: Carbohydrates
• 22.1 Introduction
• 22.2 Monosaccharides
• 22.3 Mutarotation
• 22.4 Glycoside Formation
• 22.5 Other Reactions of Monosaccharides
• 22.6 Oxidation Reactions of Monosaccharides
• 22.7 Reduction of Monosaccharides: Alditols
• 22.8 Reactions of Monosaccharides with Phenylhydrazine: Osazones
• 22.9 Synthesis and Degradation of Monosaccharides
• 22.10 The D Family of Aldoses
• 22.11 Fischer’s Proof of the Configuration of D-(+)-Glucose
• 22.12 Disaccharides
• 22.13 Polysaccharides
• 22.14 Other Biologically Important Sugars
• 22.15 Sugars That Contain Nitrogen
• 22.16 Glycolipids and Glycoproteins of the Cell Surface: Cell Recognition and the Immune System
• 22.17 Carbohydrate Antibiotics
• 22.18 Summary of Reactions of Carbohydrates
• Summary and Review Tools
• Problems
• CHAPTER 23: Lipids
• 23.1 Introduction
• 23.2 Fatty Acids and Triacylglycerols
• 23.3 Terpenes and Terpenoids
• 23.4 Steroids
• 23.5 Prostaglandins
• 23.6 Phospholipids and Cell Membranes
• 23.7 Waxes
• Summary and Review Tools
• Problems
• CHAPTER 24: Amino Acids and Proteins
• 24.1 Introduction
• 24.2 Amino Acids
• 24.3 Synthesis of α-Amino Acids
• 24.4 Polypeptides and Proteins
• 24.5 Primary Structure of Polypeptides and Proteins
• 24.6 Examples of Polypeptide and Protein Primary Structure
• 24.7 Polypeptide and Protein Synthesis
• 24.8 Secondary, Tertiary, and Quaternary Structures of Proteins
• 24.9 Introduction to Enzymes
• 24.10 Lysozyme: Mode of Action of an Enzyme
• 24.11 Serine Proteases
• 24.12 Hemoglobin: A Conjugated Protein
• 24.13 Purification and Analysis of Polypeptides and Proteins
• 24.14 Proteomics
• Summary and Review Tools
• Problems
• CHAPTER 25: Nucleic Acids and Protein Synthesis
• 25.1 Introduction
• 25.2 Nucleotides and Nucleosides
• 25.3 Laboratory Synthesis of Nucleosides and Nucleotides
• 25.4 Deoxyribonucleic Acid: DNA
• 25.5 RNA and Protein Synthesis
• 25.6 Determining the Base Sequence of DNA: The Chain-Terminating (Dideoxynucleotide) Method
• 25.7 Laboratory Synthesis of Oligonucleotides
• 25.8 Polymerase Chain Reaction
• 25.9 Sequencing of the Human Genome: An Instruction Book for the Molecules of Life
• Summary and Review Tools
• Problems
• Glossary
• Index
• Answers to Selected Problems
• Essential Tables and Charts
• PERIODIC TABLE OF THE ELEMENTS
• TABLE 3.1 Relative Strength of Selected Acids and Their Conjugate Bases
• Typical IR absorption frequencies for common functional groups
• Carbon-13 NMR Approximate Chemical Shift Ranges
• TABLE 9.2 Approximate Carbon-13 Chemical Shifts
• Hydrogen-1 NMR Approximate Chemical Shift Ranges
• TABLE 9.1 Approximate Proton Chemical Shifts
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