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Introduction
1-CHEMICAL BONDING
2-ALKANES
3-CONFORMATIONS OF ALKANES AND CYCLOALKANES
4-ALCOHOLS AND ALKYL HALIDES
5-STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS
6-REACTIONS OF ALKENES: ADDITION REACTIONS
7-STEREOCHEMISTRY
8-NUCLEOPHILIC SUBSTITUTION
9-ALKYNES
10-CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS
11-ARENES AND AROMATICITY
12-REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION
13-SPECTROSCOPY
14-ORGANOMETALLIC COMPOUNDS
15-ALCOHOLS, DIOLS, AND THIOLS
16-ETHERS, EPOXIDES, AND SULFIDES
17-ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP
18-ENOLS AND ENOLATES
19-CARBOXYLIC ACIDS
20-CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION
21-ESTER ENOLATES
22-AMINES
23-ARYL HALIDES
24-PHENOLS
25-CARBOHYDRATES
26-LIPIDS
27-AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS
APPENDIX 1 PHYSICAL PROPERTIES
APPENDIX 2 ANSWERS TO IN-TEXT PROBLEMS
APPENDIX 3 LEARNING CHEMISTRY WITH MOLECULAR MODELS: Using SpartanBuild and SpartanView
GLOSSARY
CREDITS
INDEX
INTRODUCTION
The Origins of Organic Chemistry
Berzelius, Wöhler, and Vitalism
The Structural Theory
Electronic Theories of Structure and Reactivity
The Influence of Organic Chemistry
Computers and Organic Chemistry
Challenges and Opportunities
Where Did the Carbon Come From?
CHAPTER 1- CHEMICAL BONDING
Atoms, Electrons, and Orbitals
Ionic Bonds
Covalent Bonds
Double Bonds and Triple Bonds
Polar Covalent Bonds and Electronegativity
Formal Charge
Structural Formulas of Organic Molecules
Constitutional Isomers
Resonance
The Shapes of Some Simple Molecules
Learning By Modeling
Molecular Dipole Moments
Electron Waves and Chemical Bonds
Bonding in H2: The Valence Bond Model
Bonding in H2: The Molecular Orbital Model
Bonding in Methane and Orbital Hybridization
sp3 Hybridization and Bonding in Ethane
sp2 Hybridization and Bonding in Ethylene
sp Hybridization and Bonding in Acetylene
Which Theory of Chemical Bonding Is Best?
SUMMARY
PROBLEMS
CHAPTER 2
ALKANES
Classes of Hydrocarbons
Reactive Sites in Hydrocarbons
The Key Functional Groups
Introduction to Alkanes: Methane, Ethane, and Propane
Methane and the Biosphere
The C5H12 Isomers
IUPAC Nomenclature of Unbranched Alkanes
Applying the IUPAC Rules: The Names of the C6H14 Isomers
A Brief History of Systematic Organic Nomenclature
Alkyl Groups
IUPAC Names of Highly Branched Alkanes
Cycloalkane Nomenclature
Sources of Alkanes and Cycloalkanes
Physical Properties of Alkanes and Cycloalkanes
Chemical Properties. Combustion of Alkanes
Thermochemistry
Oxidation–Reduction in Organic Chemistry
SUMMARY
PROBLEMS
CHAPTER 3
CONFORMATIONS OF ALKANES AND CYCLOALKANES
Conformational Analysis of Ethane
Conformational Analysis of Butane
Molecular Mechanics Applied to Alkanes and Cycloalkanes
Conformations of Higher Alkanes
The Shapes of Cycloalkanes: Planar or Nonplanar?
Conformations of Cyclohexane
Axial and Equatorial Bonds in Cyclohexane
Conformational Inversion (Ring Flipping) in Cyclohexane
Conformational Analysis of Monosubstituted Cyclohexanes
Enthalpy, Free Energy, and Equilibrium Constant
Small Rings: Cyclopropane and Cyclobutane
Cyclopentane
Medium and Large Rings
Conformational Analysis of Disubstituted Cyclohexanes
Polycyclic Ring Systems
Heterocyclic Compounds
SUMMARY
PROBLEMS
CHAPTER 4
ALCOHOLS AND ALKYL HALIDES
IUPAC Nomenclature of Alkyl Halides
IUPAC Nomenclature of Alcohols
Classes of Alcohols and Alkyl Halides
Bonding in Alcohols and Alkyl Halides
Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces
Acids and Bases: General Principles
Acid–Base Reactions: A Mechanism for Proton Transfer
Preparation of Alkyl Halides from Alcohols and Hydrogen Halides
Mechanism of the Reaction of Alcohols with Hydrogen Halides
Structure, Bonding, and Stability of Carbocationse
Potential Energy Diagrams for Multistep Reactions: The SN1 Mechanism
Effect of Alcohol Structure on Reaction Rate
Reaction of Primary Alcohols with Hydrogen Halides: The SN2 Mechanism
Other Methods for Converting Alcohols to Alkyl Halides
Halogenation of Alkanes
Chlorination of Methane
Structure and Stability of Free Radicals
Mechanism of Methane Chlorination
From Bond Energies to Heats of Reaction
Halogenation of Higher Alkanes
SUMMARY
PROBLEMS
CHAPTER 5
STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS
Alkene Nomenclature
Structure and Bonding in Alkenes
Isomerism in Alkenes
Naming Stereoisomeric Alkenes by the E–Z Notational System
Physical Properties of Alkenes
Relative Stabilities of Alkenes
Cycloalkenes
Preparation of Alkenes: Elimination Reactions
Dehydration of Alcohols
Regioselectivity in Alcohol Dehydration: The Zaitsev Rule
Stereoselectivity in Alcohol Dehydration
Rearrangements in Alcohol Dehydration
Dehydrohalogenation of Alkyl Halides
Mechanism of the Dehydrohalogenation of Alkyl Halides: The E2 Mechanism
Anti Elimination in E2 Reactions: Stereoelectronic Effects
A Different Mechanism for Alkyl Halide Elimination: The E1 Mechanism
SUMMARY
PROBLEMS
CHAPTER 6
REACTIONS OF ALKENES: ADDITION REACTIONS
Hydrogenation of Alkenes
Heats of Hydrogenation
Stereochemistry of Alkene Hydrogenation
Electrophilic Addition of Hydrogen Halides to Alkenes
Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule
Mechanistic Basis for Markovnikov’s Rule
Rules, Laws, Theories, and the Scientific Method
Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes
Free-Radical Addition of Hydrogen Bromide to Alkenes
Addition of Sulfuric Acid to Alkenes
Acid-Catalyzed Hydration of Alkenes
Hydroboration–Oxidation of Alkenes
Stereochemistry of Hydroboration–Oxidation
Mechanism of Hydroboration–Oxidation
Addition of Halogens to Alkenes
Stereochemistry of Halogen Addition
Mechanism of Halogen Addition to Alkenes: Halonium Ions
Epoxidation of Alkenes
Ozonolysis of Alkenes
Introduction to Organic Chemical Synthesis
Reactions of Alkenes with Alkenes: Polymerization
Ethylene and Propene: The Most Important Industrial Organic Chemicals
SUMMARY
PROBLEMS
CHAPTER 7
STEREOCHEMISTRY
Molecular Chirality: Enantiomers
The Stereogenic Center
Symmetry in Achiral Structures
Properties of Chiral Molecules: Optical Activity
Absolute and Relative Configuration
The Cahn–Ingold–Prelog R–S Notational System
Fischer Projections
Physical Properties of Enantiomers
Chiral Drugs
Reactions That Create a Stereogenic Center
Chiral Molecules with Two Stereogenic Centers
Achiral Molecules with Two Stereogenic Centers
Chirality of Disubstituted Cyclohexanes
Molecules with Multiple Stereogenic Centers
Reactions That Produce Diastereomers
Resolution of Enantiomers
Stereoregular Polymers
Stereogenic Centers Other Than Carbon
SUMMARY
CHAPTER 8
NUCLEOPHILIC SUBSTITUTION
Functional Group Transformation by Nucleophilic Substitution
Relative Reactivity of Halide Leaving Groups
The SN2 Mechanism of Nucleophilic Substitution
Stereochemistry of SN2 Reactions
How SN2 Reactions Occur
Steric Effects in SN2 Reactions
Nucleophiles and Nucleophilicity
An Enzyme-Catalyzed Nucleophilic Substitution of an Alkyl Halide
The SN1 Mechanism of Nucleophilic Substitution
Carbocation Stability and SN1 Reaction Rates
Stereochemistry of SN1 Reactions
Carbocation Rearrangements in SN1 Reactions
Effect of Solvent on the Rate of Nucleophilic Substitution
Substitution and Elimination as Competing Reactions
Sulfonate Esters as Substrates in Nucleophilic Substitution
Looking Back: Reactions of Alcohols with Hydrogen Halides
SUMMARY
PROBLEMS
CHAPTER 9
ALKYNES
Sources of Alkynes
Nomenclature
Physical Properties of Alkynes
Structure and Bonding in Alkynes: sp Hybridization
Acidity of Acetylene and Terminal Alkynes
Natural and “Designed” Enediyne Antibiotics
Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes
Preparation of Alkynes by Elimination Reactions
Reactions of Alkynes
Metal–Ammonia Reduction of Alkynes
Addition of Hydrogen Halides to Alkynes
Hydration of Alkynes
Addition of Halogens to Alkynes
Ozonolysis of Alkynes
SUMMARY
PROBLEMS
CHAPTER 10
CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS
The Allyl Group
Allylic Carbocations
Allylic Free Radicals
Classes of Dienes
Relative Stabilities of Dienes
Bonding in Conjugated Dienes
Bonding in Allenes
Preparation of Dienes
Addition of Hydrogen Halides to Conjugated Dienes
Halogen Addition to Dienes
Diene Polymers
The π Molecular Orbitals of Ethylene and 1,3-Butadiene
A π Molecular Orbital Analysis of the Diels–Alder Reaction
SUMMARY
PROBLEMS
CHAPTER 11
ARENES AND AROMATICITY
Benzene
Kekulé and the Structure of Benzene
Benzene, Dreams, and Creative Thinking
A Resonance Picture of Bonding in Benzene
The Stability of Benzene
An Orbital Hybridization View of Bonding in Benzene
The π Molecular Orbitals of Benzene
Substituted Derivatives of Benzene and Their Nomenclature
Polycyclic Aromatic Hydrocarbons
Carbon Clusters, Fullerenes, and Nanotubes
Physical Properties of Arenes
Reactions of Arenes: A Preview
The Birch Reduction
Free-Radical Halogenation of Alkylbenzenes
Oxidation of Alkylbenzenes
Nucleophilic Substitution in Benzylic Halides
Preparation of Alkenylbenzenes
Addition Reactions of Alkenylbenzenes
Polymerization of Styrene
Cyclobutadiene and Cyclooctatetraene
Hückel’s Rule: Annulenes
Aromatic Ions
Heterocyclic Aromatic Compounds
Heterocyclic Aromatic Compounds and Hückel’s Rule
SUMMARY
PROBLEMS
CHAPTER 12
REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION
Representative Electrophilic Aromatic Substitution Reactions of Benzene
Mechanistic Principles of Electrophilic Aromatic Substitution
Nitration of Benzene
Sulfonation of Benzene
Halogenation of Benzene
Friedel–Crafts Alkylation of Benzene
Friedel–Crafts Acylation of Benzene
Synthesis of Alkylbenzenes by Acylation–Reduction
Rate and Regioselectivity in Electrophilic Aromatic Substitution
Rate and Regioselectivity in the Nitration of Toluene
Rate and Regioselectivity in the Nitration of (Trifluoromethyl)benzene
Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents
Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents
Substituent Effects in Electrophilic Aromatic Substitution: Halogens
Multiple Substituent Effects
Regioselective Synthesis of Disubstituted Aromatic Compounds
Substitution in Naphthalene
Substitution in Heterocyclic Aromatic Compounds
SUMMARY
PROBLEMS
CHAPTER 13
SPECTROSCOPY
Principles of Molecular Spectroscopy: Electromagnetic Radiation
Principles of Molecular Spectroscopy: Quantized Energy States
Introduction to 1H NMR Spectroscopy
Nuclear Shielding and 1H Chemical Shifts
Effects of Molecular Structure on 1H Chemical Shifts
Interpreting Proton NMR Spectra
Spin–Spin Splitting in NMR Spectroscopy
Splitting Patterns: The Ethyl Group
Splitting Patterns: The Isopropyl Group
Splitting Patterns: Pairs of Doublets
Complex Splitting Patterns
1 H NMR Spectra of Alcohols
NMR and Conformations
13 C NMR Spectroscopy
13 C Chemical Shifts
13 C NMR and Peak Intensities
13 C—1H Coupling
Using DEPT to Count the Hydrogens Attached to 13C
Magnetic Resonance Imaging
Infrared Spectroscopy
Ultraviolet-Visible (UV-VIS) Spectroscopy
Mass Spectrometry
Gas Chromatography, GC/MS, and MS/MS
Molecular Formula as a Clue to Structure
SUMMARY
PROBLEMS
CHAPTER 14
ORGANOMETALLIC COMPOUNDS
Organometallic Nomenclature
Carbon–Metal Bonds in Organometallic Compounds
Preparation of Organolithium Compounds
Preparation of Organomagnesium Compounds: Grignard Reagents
Organolithium and Organomagnesium Compounds as Brønsted Bases
Synthesis of Alcohols Using Grignard Reagents
Synthesis of Alcohols Using Organolithium Reagents
Synthesis of Acetylenic Alcohols
Retrosynthetic Analysis
Preparation of Tertiary Alcohols from Esters and Grignard Reagents
Alkane Synthesis Using Organocopper Reagents
An Organozinc Reagent for Cyclopropane Synthesis
Carbenes and Carbenoids
Transition-Metal Organometallic Compounds
Ziegler–Natta Catalysis of Alkene Polymerization
An Organometallic Compound That Occurs Naturally: Coenzyme B12
SUMMARY
PROBLEMS
CHAPTER 15
ALCOHOLS, DIOLS, AND THIOLS
Sources of Alcohols
Preparation of Alcohols by Reduction of Aldehydes and Ketones
Preparation of Alcohols by Reduction of Carboxylic Acids and Esters
Preparation of Alcohols from Epoxides
Preparation of Diols
Reactions of Alcohols: A Review and a Preview
Conversion of Alcohols to Ethers
Esterification
Esters of Inorganic Acids
Oxidation of Alcohols
Economic and Environmental Factors in Organic Synthesis
Biological Oxidation of Alcohols
Oxidative Cleavage of Vicinal Diols
Preparation of Thiols
Properties of Thiols
Spectroscopic Analysis of Alcohols
SUMMARY
PROBLEMS
CHAPTER 16
ETHERS, EPOXIDES, AND SULFIDES
Nomenclature of Ethers, Epoxides, and Sulfides
Structure and Bonding in Ethers and Epoxides
Physical Properties of Ethers
Crown Ethers
Polyether Antibiotics
Preparation of Ethers
The Williamson Ether Synthesis
Reactions of Ethers: A Review and a Preview
Acid-Catalyzed Cleavage of Ethers
Preparation of Epoxides: A Review and a Preview
Conversion of Vicinal Halohydrins to Epoxides
Reactions of Epoxides: A Review and a Preview
Nucleophilic Ring-Opening Reactions of Epoxides
Acid-Catalyzed Ring-Opening Reactions of Epoxides
Epoxides in Biological Processes
Preparation of Sulfides
Oxidation of Sulfides: Sulfoxides and Sulfones
Alkylation of Sulfides: Sulfonium Salts
Spectroscopic Analysis of Ethers
SUMMARY
PROBLEMS
CHAPTER 17
ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP
Nomenclature
Structure and Bonding: The Carbonyl Group
Physical Properties
Sources of Aldehydes and Ketones
Reactions of Aldehydes and Ketones: A Review and a Preview
Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones
Cyanohydrin Formation
Acetal Formation
Acetals as Protecting Groups
Reaction with Primary Amines: Imines
Reaction with Secondary Amines: Enamines
Imines in Biological Chemistry
The Wittig Reaction
Planning an Alkene Synthesis via the Wittig Reaction
Stereoselective Addition to Carbonyl Groups
Oxidation of Aldehydes
Baeyer–Villiger Oxidation of Ketones
Spectroscopic Analysis of Aldehydes and Ketones
SUMMARY
PROBLEMS
CHAPTER 18
ENOLS AND ENOLATES
The ␣-Carbon Atom and Its Hydrogens
␣ Halogenation of Aldehydes and Ketones
Mechanism of ␣ Halogenation of Aldehydes and Ketones
Enolization and Enol Content
Stabilized Enols
Base-Catalyzed Enolization: Enolate Anions
The Haloform Reaction
The Haloform Reaction and the Biosynthesis of Trihalomethanes
Some Chemical and Stereochemical Consequences of Enolization
The Aldol Condensation
Mixed Aldol Condensations
Effects of Conjugation in ␣,-Unsaturated Aldehydes and Ketones
Conjugate Addition to ␣,-Unsaturated Carbonyl Compounds
Additions of Carbanions to ␣,-Unsaturated Ketones: The Michael Reaction
Alkylation of Enolate Anions
SUMMARY
PROBLEMS
CHAPTER 19
CARBOXYLIC ACIDS
Carboxylic Acid Nomenclature
Structure and Bonding
Physical Properties
Acidity of Carboxylic Acids
Salts of Carboxylic Acids
Quantitative Relationships Involving Carboxylic Acids
Substituents and Acid Strength
Ionization of Substituted Benzoic Acids
Dicarboxylic Acids
Carbonic Acid
Sources of Carboxylic Acids
Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents
Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles
Reactions of Carboxylic Acids: A Review and a Preview
Mechanism of Acid-Catalyzed Esterification
Intramolecular Ester Formation: Lactones
␣ Halogenation of Carboxylic Acids: The Hell–Volhard–Zelinsky Reaction
Decarboxylation of Malonic Acid and Related Compounds
Spectroscopic Analysis of Carboxylic Acids
SUMMARY
PROBLEMS
CHAPTER 20
CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION
Nomenclature of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Nucleophilic Substitution in Acyl Chlorides
Preparation of Carboxylic Acid Anhydrides
Reactions of Carboxylic Acid Anhydrides
Sources of Esters
Physical Properties of Esters
Reactions of Esters: A Review and a Preview
Acid-Catalyzed Ester Hydrolysis
Ester Hydrolysis in Base: Saponification
Reaction of Esters with Ammonia and Amines
Thioesters
Preparation of Amides
The Hofmann Rearrangement
Condensation Polymers: Polyamides and Polyesters
Preparation of Nitriles
Hydrolysis of Nitriles
Addition of Grignard Reagents to Nitriles
Spectroscopic Analysis of Carboxylic Acid Derivatives
SUMMARY
PROBLEMS
CHAPTER 21
ESTER ENOLATES
The Claisen Condensation
Intramolecular Claisen Condensation: The Dieckmann Reaction
Mixed Claisen Condensations
Acylation of Ketones with Esters
Ketone Synthesis via -Keto Esters
The Acetoacetic Ester Synthesis
The Malonic Ester Synthesis
Barbiturates
Michael Additions of Stabilized Anions
␣ Deprotonation of Carbonyl Compounds by Lithium Dialkylamides
SUMMARY
PROBLEMS
CHAPTER 22
AMINES
Amine Nomenclature
Structure and Bonding
Physical Properties
Measures of Amine Basicity
Basicity of Amines
Amines as Natural Products
Tetraalkylammonium Salts as Phase-Transfer Catalysts
Reactions That Lead to Amines: A Review and a Preview
Preparation of Amines by Alkylation of Ammonia
The Gabriel Synthesis of Primary Alkylamines
Preparation of Amines by Reduction
Reductive Amination
Reactions of Amines: A Review and a Preview
Reaction of Amines with Alkyl Halides
Electrophilic Aromatic Substitution in Arylamines
Nitrosation of Alkylamines
Nitrosation of Arylamines
Synthetic Transformations of Aryl Diazonium Salts
Azo Coupling
From Dyes to Sulfa Drugs
Spectroscopic Analysis of Amines
SUMMARY
PROBLEMS
CHAPTER 23
ARYL HALIDES
Bonding in Aryl Halides
Sources of Aryl Halides
Physical Properties of Aryl Halides
Reactions of Aryl Halides: A Review and a Preview
Nucleophilic Substitution in Nitro-Substituted Aryl Halides
The Addition–Elimination Mechanism of Nucleophilic Aromatic Substitution
Related Nucleophilic Aromatic Substitution Reactions
The Elimination–Addition Mechanism of Nucleophilic Aromatic Substitution: Benzyne
Diels–Alder Reactions of Benzyne
SUMMARY
PROBLEMS
CHAPTER 24
PHENOLS
Nomenclature
Structure and Bonding
Physical Properties
Acidity of Phenols
Substituent Effects on the Acidity of Phenols
Sources of Phenols
Naturally Occurring Phenols
Reactions of Phenols: Electrophilic Aromatic Substitution
Acylation of Phenols
Carboxylation of Phenols: Aspirin and the Kolbe–Schmitt Reaction
Preparation of Aryl Ethers
Agent Orange and Dioxin
Cleavage of Aryl Ethers by Hydrogen Halides
Claisen Rearrangement of Allyl Aryl Ethers
Oxidation of Phenols: Quinones
Spectroscopic Analysis of Phenols
SUMMARY
PROBLEMS
CHAPTER 25
CARBOHYDRATES
Classification of Carbohydrates
Fischer Projections and the D–L Notation
The Aldotetroses
Aldopentoses and Aldohexoses
A Mnemonic for Carbohydrate Configurations
Cyclic Forms of Carbohydrates: Furanose Forms
Cyclic Forms of Carbohydrates: Pyranose Forms
Mutarotation
Ketoses
Deoxy Sugars
Amino Sugars
Glycosides
Disaccharides
Polysaccharides
Cell-Surface Glycoproteins
Carbohydrate Structure Determination
Reduction of Carbohydrates
How Sweet It Is!
Oxidation of Carbohydrates
Cyanohydrin Formation and Carbohydrate Chain Extension
Epimerization, Isomerization, and Retro-Aldol Cleavage Reactions of Carbohydrates
Acylation and Alkylation of Hydroxyl Groups in Carbohydrates
Periodic Acid Oxidation of Carbohydrates
SUMMARY
PROBLEMS
CHAPTER 26
LIPIDS
Acetyl Coenzyme A
Fats, Oils, and Fatty Acids
atty Acid Biosynthesis
Phospholipids
Waxes
Terpenes: The Isoprene Rule
sopentenyl Pyrophosphate: The Biological Isoprene Unit
Carbon–Carbon Bond Formation in Terpene Biosynthesis
The Pathway from Acetate to Isopentenyl Pyrophosphate
Steroids: Cholesterol
Good Cholesterol? Bad Cholesterol? What’s the Difference?
Vitamin D
Bile Acids
Corticosteroids
Sex Hormones
Anabolic Steroids
Carotenoids
SUMMARY
PROBLEMS
CHAPTER 27
AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS
Classification of Amino Acids
tereochemistry of Amino Acids
Acid–Base Behavior of Amino Acids
Electrophoresis
Synthesis of Amino Acids
Reactions of Amino Acids
Some Biochemical Reactions of Amino Acids
Peptides
Introduction to Peptide Structure Determination
Amino Acid Analysis
Partial Hydrolysis of Peptides
End Group Analysis
Insulin
The Edman Degradation and Automated Sequencing of Peptides
The Strategy of Peptide Synthesis
Amino Group Protection
Carboxyl Group Protection
Peptide Bond Formation
Solid-Phase Peptide Synthesis: The Merrifield Method
Secondary Structures of Peptides and Proteins
Tertiary Structure of Peptides and Proteins
Coenzymes
Protein Quaternary Structure: Hemoglobin
Pyrimidines and Purines
Nucleosides
Nucleotides
Nucleic Acids
Structure and Replication of DNA: The Double Helix
AIDS
DNA Sequencing
SUMMARY
PROBLEMS
APPENDIX 1 PHYSICAL PROPERTIES A-1
APPENDIX 2 ANSWERS TO IN-TEXT PROBLEMS A-9
APPENDIX 3 LEARNING CHEMISTRY WITH MOLECULAR MODELS: Using SpartanBuild and SpartanView A-64
GLOSSARY G-1
CREDITS C-1
INDEX I-1
Chemistry
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