Francis Carey,
University of Virginia, Charlottesville
ISBN: 0072424583 Copyright year: 2003
Detailed Table of Contents
Table of Contents Introduction -- The Origins of Organic Chemistry Berzelius,
Wöhler, and Vitalism The Structural Theory Electronic Theories of
Structure and Reactivity The Impact of Organic Chemistry Computers and
Organic Chemistry Challenges and Opportunities
Chapter 1 -- Structure Determines Properties1.1 Atoms, Electrons, and
Orbitals 1.2 Ionic
Bonds 1.3 Covalent
Bonds 1.4 Double Bonds and Triple
Bonds 1.5 Polar Covalent Bonds and
Electronegativity Electrostatic Potential Maps 1.6
Formal Charge 1.7 Structural Formulas of
Organic Molecules 1.8 Constitutional
Isomers 1.9
Resonance Learning by Modeling 1.10 The Shapes of Some
Simple Molecules 1.11 Molecular Dipole
Moments Curved Arrows 1.12 Acids and Bases: The
Arrhenius View 1.13 Acids and Bases: The
Brønsted-Lowry View 1.14 What Happened to
pKb? 1.15 How Structure Affects Acid
Strength 1.16 Acid-Base
Equilibria 1.17 Lewis Acids and Lewis
Bases 1.18 Summary
Problems
Chapter 2 -- Hydrocarbon Frameworks. Alkanes2.1 Classes of
Hydrocarbons 2.2 Electron Waves and
Chemical Bonds 2.3 Bonding in H2: The
Valence Bond Model 2.4 Bonding in H2: The
Molecular Orbital Model 2.5 Introduction
to Alkanes: Methane, Ethane, and
Propane Methane and the Biosphere 2.6 sp3
Hybridization and Bonding in
Methane 2.7 sp3 Hybridization and Bonding
in Ethane 2.8 Isomeric Alkanes: The
Butanes 2.9 Higher
n
-Alkanes 2.10 The C5H12 Isomers 2.11
IUPAC Nomenclature of Unbranched
Alkanes A Brief History of Systematic Organic Nomenclature 2.12 Applying
the IUPAC Rules: The Names of the C6H14 Isomers 2.13 Alkyl
Groups 2.14 IUPAC Names of Highly Branched
Alkanes 2.15 Cycloalkane
Nomenclature 2.16 Sources of Alkanes and
Cycloalkanes 2.17 Physical Properties of Alkanes and
Cycloalkanes 2.18 Chemical Properties. Combustion of
Alkanes Thermochemistry 2.19 Oxidation-Reduction in
Organic Chemistry 2.20 sp3 Hybridization and Bonding in Ethylene 2.21 sp
Hybridization and Bonding in Acetylene 2.22 Which Theory of Chemical
Bonding is Best? 2.23 Summary
Problems
Chapter 3 -- Conformations of Alkanes and
Cycloalkanes3.1 Conformational Analysis of Ethane 3.2 Conformational Analysis
of Butane Molecular Mechanics Applied to Alkanes and
Cycloalkanes 3.3 Conformations of Higher Alkanes 3.4 The Shapes of
Cycloalkanes: Planar or Nonplanar 3.5 Small Rings: Cyclopropane and
Cyclobutane 3.6 Cyclopentane 3.7 Conformations of
Cyclohexane 3.8 Axial and Equatorial Bonds in Cyclohexane 3.9
Conformational Inversion (Ring Flipping) in Cyclohexane 3.10
Conformational Analysis of Monosubstituted Cyclohexanes Enthalpy,
Free Energy, and Equilibrium Constant 3.11 Disubstituted Cycloalkanes.
Stereoisomers 3.12 Conformational Analysis of Disubstituted
Cyclohexanes 3.13 Medium and Large Rings 3.14 Polycyclic Ring
Systems 3.15 Heterocyclic Compounds 3.16 Summary
Problems
Chapter 4 -- Alcohols and Alkyl
Halides4.1 Functional Groups 4.2 IUPAC Nomenclature of Alkyl
Halides 4.3 IUPAC Nomenclature of Alcohols 4.4 Classes of Alcohols
and Alkyl Halides 4.5 Bonding in Alcohols and Alkyl Halides 4.6 Physical Properties of Alcohols and Alkyl Halides: Intermolecular
Forces 4.7 Preparation of Alkyl Halides From Alcohols and Hydrogen
Halides 4.8 Mechanism of the Reaction of Alcohols with Hydrogen
Halides 4.9 Potential Energy Diagrams for Multistep Reactions. The SN1
Mechanism 4.10 Structure, Bonding, and Stability of
Carbocations 4.11 Effect of Alcohol Structure on Reaction
Rate 4.12 Reaction of Primary Alcohols with Hydrogen Halides. The SN2
Mechanism 4.13 Other Methods for Converting Alcohols to Alkyl
Halides 4.14 Halogenation of Alkanes 4.15 Chlorination of
Methane 4.16 Structure and Stability of Free Radicals 4.17
Mechanism of Methane Chlorination
From Bond Energies to Heats of Reaction 4.18 Halogenation of Higher Alkanes 4.19 Summary
Problems
Chapter 5 -- Structure and Preparation of Alkenes:
Elimination Reactions5.1 Alkene Nomenclature Ethylene 5.2 Structure and Bonding
in Alkenes 5.3 Isomerism in Alkenes 5.4 Naming Stereoisomeric
Alkenes by the E-Z Notational System 5.5 Physical Properties on
Alkenes 5.6 Relative Stabilities of Alkenes 5.7 Cycloalkenes 5.8 Preparations of Alkenes: Elimination
Reactions 5.9 Dehydration of Alcohols 5.10 Regioselectivity in
Alcohol Dehydration: The Zaitsev Rule 5.11 Stereoselectivity in Alcohol
Dehydration 5.12 The E1 and E2 Mechanisms of Alcohol
Dehydration 5.13 Rearrangements in Alcohol Dehydration 5.14
Dehydrohalogenation of Alkyl Halides 5.15 The E2 Mechanism of
Dehydrohalogenation of Alkyl Halides 5.16 Anti Elimination in E2
Reactions: Stereoelectronic Effects 5.17 The E1 Mechanism of
Dehydrohalogenation of Alkyl Halides 5.18 Summary
Problems
Chapter 6 -- Reactions of Alkenes: Addition
Reactions6.1 Hydrogenation of Alkenes 6.2 Heats of Hydrogenation 6.3 Stereochemistry of Alkene Hydrogenation 6.4 Electrophilic Addition of
Hydrogen Halides 6.5 Regioselectivity of Hydrogen Halide Addition:
Markovnikov's Rule 6.6 Mechanistic Basis for Markovnikov's
Rule Rules, Laws, Theories, and the Scientific Method 6.7 Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes 6.8 Free-Radical Addition of Hydrogen Bromide to Alkenes 6.9 Addition of
Sulfuric Acid to Alkenes 6.10 Acid-Catalyzed Hydration of
Alkenes 6.11 Hydroboration-Oxidation of Alkenes 6.12
Stereochemistry of Hydroboration-Oxidation 6.13 Mechanism of
Hydroboration-Oxidation 6.14 Addition of Halogens to Alkenes 6.15
Stereochemistry of Halogen Addition 6.16 Mechanism of Halogen Addition to
Alkenes: Halonium Ions 6.17 Conversion of Alkenes to Vicinal
Halohydrins 6.18 Epoxidation of Alkenes 6.19 Ozonolysis of
Alkenes 6.20 Introduction to Organic Chemical Synthesis 6.21
Reactions of Alkenes with Alkenes: Polymerization Ethylene and Propane: The Most Important Industrial Organic
Chemicals 6.22 Summary
Problems
Chapter 7 -- Stereochemistry7.1 Molecular Chirality: Enantiomers 7.2 The Chirality
Center 7.3 Symmetry in Achiral Structures 7.4 Optical
Activity 7.5 Absolute and Relative Configuration 7.6 The
Cahn-Ingold-Prelog R-S Notation System 7.7 Fischer Projections 7.8
Properties of Enantiomers Chiral Drugs 7.9 Reactions That Create a
Chirality Center 7.10 Chiral Molecules With Two Chirality
Centers 7.11 Achiral Molecules With Two Chirality
Centers Chirality of Disubstituted Cyclohexanes 7.12 Molecules
With Multiple Chirality Centers 7.13 Reactions That Produce
Diastereomers 7.14 Resolution of Enantiomers 7.15 Stereoregular
Polymers 7.16 Chirality Centers Other Than Carbon 7.17 Summary
Problems
Chapter 8 -- Nucleophilic
Substitution8.1 Functional Group Transformation by Nucleophilic
Substitution 8.2 Relative Reactivity of Halide Leaving Groups 8.3
The SN2 Mechanism of Nucleophilic Substitution 8.4 Stereochemistry of SN2
Reactions 8.5 How SN2 Reactions Occur 8.6 Steric Effects in SN2
Reactions 8.7 Nucleophiles and Nucleophilicity An Enzyme-catalyzed
Nucleophilic Substitution of and Alkyl Halide 8.8 The SN1 Mechanism of
Nucleophilic Substitution 8.9 Carbocation Stability and SN1 Reaction
Rates 8.10 Stereochemistry of SN1 Reactions 8.11 Carbocation
Rearrangements in SN1 Reactions 8.12 Effect of Solvent on the Rate of
Nucleophilic Substitution 8.13 Substitution and Elimination as Competing
Reactions 8.14 Sulfonate Esters as Substrates in Nucleophilic
Substitution 8.15 Looking Back: Reactions of Alcohols with Hydrogen
Halides 8.16 Summary
Problems
Chapter 9 -- Alkynes 9.1 Sources of Alkynes 9.2 Nomenclature 9.3 Physical
Properties of Alkynes 9.4 Structure and
Bonding in Alkynes: sp
Hybridization Natural and "Designed" Enediyne Antibiotics 9.5
Acidity of Acetylene and Terminal Alkynes 9.6 Preparation of Alkynes by
Alkylation of Acetylene and Terminal Alkynes 9.7 Preparation of Alkynes
by Elimination Reactions 9.8 Reactions of Alkynes 9.9
Hydrogenation of Alkynes 9.10 Metal-Ammonia Reduction of
Alkynes 9.11 Addition of Hydrogen Halides to Alkynes 9.12
Hydration of Alkynes 9.13 Addition of Halogens to Alkynes 9.14
Ozonolysis of Alkynes 9.16 Summary
Problems
Chapter 10 - Conjugation in alkadienes and
Allylic Systems 10.1 The Allyl Group 10.2 Allylic Carbocations 10.3 Allylic
Free Radicals 10.4 Allylic Halogenation 10.5 Classes of
Dienes 10.6 Relative Stabilities of Dienes 10.7 Bonding in
Conjugated Dienes 10.8 Bonding in Allenes 10.9 Preparation of
Dienes 10.10 Addition of Hydrogen Halides to Conjugated
Dienes 10.11 Halogen Addition to Dienes Diene
Polymers 10.12 The Diels-Alder Reaction 10.13 The p Molecular
Orbitals of Ethylene and 1,3-Butadiene 10.14 A p Molecular Orbital
Analysis of the Diels-Alder Reaction 10.15 Summary
Problems
Chapter 11 -Arenes and Aromaticity11.1 Benzene 11.2 Kekule and the Structure of
Benzene Benzene, Dreams, and Creative Thinking 11.3 A Resonance
Picture of Bonding in Benzene 11.4 The stability of Benzene 11.5
An Orbital hybridization View of Bonding in Benzene 11.6 The p Molecular
Orbitals of Benzene 11.7 Substituted Derivatives of Benzene and their
Nomenclature 11.8 Polycyclic Aromatic Hydrocarbons
Carbon
Clusters, Fullerenes, and Nanotubes 11.9 Physical Properties of
Arenes 11.10 Reactions of Arenes. A Preview. 11.11 The Birch
Reduction 11.12 Free-Radical Halogenation of Alkylbenzenes 11.13 Oxidation of Alkylbenzenes 11.14 Nucleophilic Substitution in Benzylic
Halides 11.15 Preparation of Alkenylbenzenes' 11.16 Addition
Reactions of Alkenylbenzenes 11.17 Polymerization of Styrene 11.18 Cyclobutadiene and Cyclooctatetraene 11.19 Huckel's Rule 11.20 Annulenes 11.21 Aromatic Ions 11.22 Heterocyclic Aromatic
Compounds 11.23 Heterocyclic Aromatic Compounds and Huckel's
Rule 11.24 Summary
Problems
Chapter 12 - Reactions of Arenes.
Electrophilic Aromatic Substitution12.1 Representative Electrophilic Aromatic Substitution Reactions
of Benzene 12.2 Mechanistic Principles of Electrophilic Aromatic
Substitution 12.3 Nitration of Benzene 12.4 Sulfonation of
Benzene 12.5 Halogenation of Benzene 12.6 Friedel-Crafts
Alkylation of Benzene 12.7 Friedel-Crafts Acylation of
Benzene 12.8 Synthesis of Alkylbenzenes by
Acylation-Reduction 12.9 Rate and Regioselectivity in Electrophilic
Aromatic Substitution 12.10 Rate and Regioselectivity in the Nitration of
Toluene 12.11 Rate and Regioselectivity in the Nitration of
(Trifluoromethyl)Benzene 12.12 Substituent Effects in Electrophilic
Aromatic Substitution Activating
Substituents 12.13 Substituent
Effects in Electrophilic Aromatic Substitution Strongly Deactivating
Substituents 12.14 Substituent Effects in Electrophilic Aromatic
Substitution Halogens 12.15 Multiple Substituent
Effects 12.16 Regioselective Synthesis of Disubstituted Aromatic
compounds 12.17 Substitution in Naphthalene 12.18 Substitution in
Heterocyclic Aromatic Compounds 12.19 Summary
Problems
Chapter 13 - Spectroscopy13.1 Principles of Molecular Spectroscopy Electromagnetic
Radiation 13.2 Principles of Molecular Spectroscopy Quantized
Energy States 13.3 Introduction to 1H NMR Spectroscopy 13.4
Nuclear Shielding and 1H Chemical Shifts 13.5 Effects of Molecular
Structure on 1H Chemical Shifts Ring Currents-Aromatic and
Antiaromatic 13.6 Interpreting 1H NMR Spectra 13.7 Spin-Spin
Splitting in 1H NMR 13.8 Splitting Patterns: The Ethyl Group 13.9 Splitting Patterns: The Isopropyl Group 13.10 Splitting Patterns: Pairs
of Doublets 13.11 Complex Splitting Patterns 13.12 1H NMR Spectra
of Alcohols 13.13 NMR and Conformations Magnetic
Resonance Imaging 13.14 13C NMR Spectroscopy 13.15 13C NMR Chemical
shifts 13.16 13C NMR and Peak Intensities 13.17 13C-1H
Coupling 13.18 Using Dept to Count Hydrogens Attached to 13C 13.19
2D NMR: Cosy and Hetcor Spectra by the Thousands 13.20 Infrared
Spectroscopy 13.21 Ultraviolet-Visible (UV-Vis) Spectroscopy 13.22
Mass Spectrometry Gas Chromatography, GC/MS, and MS/MS 13.23
Molecular Formula as a Clue to Structure 13.24 Summary
Problems
Chapter 14 - Organometallic
Compounds14.1 Organometallic Nomenclature 14.2 Carbon-Metal Bonds in
Organometallic Compounds 14.3 Preparation of Organolithium
compounds 14.4 Preparation of Organomagnesium Compounds Grignard
Reagents 14.5 Organolithium and Organomagnesium Compounds as Bronsted
Bases 14.6 Synthesis of Alcohols Using Grignard Reagents 14.7
Synthesis of Alcohols Using Organolithium Reagents 14.8 Synthesis of
Acetylenic Alcohols 14.9 Retrosynthetic Analysis 14.10 Preparation
of Tertiary Alcohols From Esters and Grignard Reagents 14.11 Alkane
Synthesis Using Organocopper Reagents 14.12 An Organozinc Reagent for
Cyclopropane Synthesis 14.13 Carbenes and Carbenoids 14.14
Transition-Metal Organometallic Compounds An Organometallic That Occurs
Naturally. Coenzyme B12 14.15 Ziegler-Natta Catalysis of Alkene
Polymerization 14.16 Summary
Problems
Chapter 15 - Alcohols, Diols, and
Thiols15.1 Sources of Alcohols 15.2 Preparation of Alcohols by Reduction
of Aldehydes and Ketones 15.3 Preparation of Alcohols by Reduction of
Carboxylic Acids and Esters 15.4 Preparation of Alcohols from
Epoxides 15.5 Preparation of Diols 15.6 Reactions of Alcohols: A
Review and a Preview 15.7 Conversion of Alcohols to Ethers 15.8
Esterification 15.9 Esters of Inorganic Acids 15.10 Oxidaton of
Alcohols Economic and Environmental Factors in Organic
Synthesis 15.11 Biological Oxidation of Alcohols 15.12 Oxidative
Cleavage of Vicinal Diols 15.13 Thiols 15.14 Spectroscopic
Analysis of Alcohols and Thiols 15.15 Summary
Problems
Chapter 16 - Ethers, Epoxides, and
Sulfides16.1 Nomenclature of Ethers, Epoxides, and Sulfides 16.2 Structure
and bonding in Ethers and Epoxides 16.3 Physical Properties of
Ethers 16.4 Crown Ethers Polyether Antibiotics 16.5
Preparation of Ethers 16.6 The Williamson Ether Synthesis 16.7
Reactions of Ethers: A Review and a Preview 16.8 Acid-Catalyzed Cleavage
of Ethers 16.9 Preparation of Epoxides: A Review and a
Preview 16.10 Conversion of Vicinal Halohydrins to Epoxides 16.11
Reactions of Epoxides: A Review and a Preview 16.12 Nucleophilic
Ring-Opening of Epoxides 16.13 Acid-Catalyzed Ring-Opening of
Epoxides 16.14 Epoxides in Biological Processes 16.15 Preparation
of Sulfides 16.16 Oxidation of Sulfides: Sulfoxides and
Sulfones 16.17 Alkylation of Sulfides: Sulfonium Salts 16.18
Spectroscopic Analysis of Ethers, Epoxides, and Sulfides 16.19 Summary
Problems
Chapter 17 - Aldehydes and Ketones.
Nucleophilic Addition to the Carbonyl Group17.1 Nomenclature 17.2 Structure and bonding: The Carbonyl
Group 17.3 Physical Properties 17.4 Sources of Aldehydes and
Ketones 17.5 Reactions of Aldehydes and Ketones. A Review and a
Preview 17.6 Principles of Nucleophilic Addition: Hydration of Aldehydes
and Ketones 17.7 Cyanohydrin Formation 17.8 Acetal
Formation 17.9 Acetals as Protecting Groups 17.10 Reaction with
Primary Amines: Imines Imines in Bioligical Chemistry 17.11
Reaction with Secondary Amines: Enamines 17.12 The Wittig
Reaction 17.13 Planning an Alkene Synthesis via the Wittig
Reaction 17.14 Stereoselective Addition to Carbonyl Groups 17.15
Oxidation of Aldehydes 17.16 Baeyer-Villiger Oxidation of
Ketones 17.17 Spectroscopic Analysis of Aldeyhdes and
Ketones 17.18 Summary
Problems
Chapter 18 - Enols and Enolates18.1 The a-Carbon Atom and its Hydrogens 18.2 a Halogenation of
Aldehydes and Ketones 18.3 Mechanism of a Halogenation of Aldehydes and
Ketones 18.4 Enolization and Enol Content 18.5 Stabilized
Enols 18.6 Base-Catalyzed Enolization: Enolate Anions 18.7 The
Haloform Reaction
The Haloform reaction and the biosynthesis of
Trihalomethanes 18.8 Some Chemical And Stereochemical Consequences of
Enolization 18.9 The Aldol Condensation 18.10 Mixed Aldol
Condensations 18.11 Effects of Conjugation in a,ß-Unsaturated Aldehydes
and Ketones 18.12 Conjugate addition to a,ß-Unsaturated Carbonyl
compounds 18.13 Addition of carbanions to a,ß-Unsaturated Ketones: The
Michael Reaction 18.14 Conjugate Addition of Organocopper Reagents to
a,ß-Unsaturated Carbonyl Compounds 18.15 Alkylation of Enolate
Anions 18.16 Summary
Problems
Chapter 19 - Carboxylic Acids19.1 Carboxylic Acid Nomenclature 19.2 Structure and
Bonding 19.3 Physical Properties 19.4 Acidity of Carboxylic
Acids 19.5 Salts of Carboxylic Acids 19.6 Substituents and Acid
Strength 19.7 Ionizaton of Substituted Benzoic Acids 19.8
Dicarboxylic Acids 19.9 Carbonic Acid 19.10 Sources of Carboxylic
Acids 19.11 Synthesis of Carboxylic Acids by the Carboxylation of
Grignard Reagents 19.12 Synthesis of Carboxylic Acids by the Preparation
and Hydrolysis of Nitriles 19.13 Reactions of Carboxylic Acids: A Review
and a Preview 19.14 Mechanism of Acid-Catalyzed
Esterification 19.15 Intramolecular Ester Formation.
Lactones 19.16 a-Halogenation of Carboxylic Acids. The
Hell-Volhardzelinsky Reaction 19.17 Decarboxylation of Malonic Acid and
Related Compounds 19.18 Spectroscopic Properties of Carboxylic
Acids 19.19 Summary
Problems
Chapter 20 - Carboxylic Acid Derivatives:
Nucleophilic Acyl Substitution
20.1 Nomenclature of Carboxylic Acid Derivatives 20.2 Structure
and Reactivity of Carboxylic Acid Derivatives 20.3 General Mechanism for
Nucleophilic Acyl Substitution 20.4 Nucleophilic Substitution in Acyl
Chlorides 20.5 Preparation of Carboxylic Acid Anhydrides 20.6
Reactions of Carboxylic Acid Anhydrides 20.7 Sources of
Esters 20.8 Physical Properties of Esters 20.9 Reactions of
Esters: A review and a Preview 20.10 Acid-Catalyzed Ester
Hydrolysis 20.11 Ester Hydrolysis in Base: Saponification 20.12 Reaction of Esters with Ammonia and Amines 20.13 Thioesters 20.14
Preparation of Amides 20.15 Lactams 20.16 Imides 20.17 Hydrolysis of Amides Condensation Polymers. Polyamides and
Polyesters 20.18 Preparation of Nitriles 20.19 Hydrolysis of
Nitriles 20.20 Addition of Grignard Reagents to Nitriles 20.21
Spectroscopic Analysis of carboxylic Acid Derivatives 20.22 Summary
Problems
Chapter 21 - Ester Enolates21.1 The Claisen Condensation 21.2 Intramolecular Claisen
Condensation: The Dieckmann Reaction 21.3 Mixed Claisen
Condensations 21.4 Acylation of Ketones with Esters 21.5 Ketone
Synthesis via b-Keto Esters 21.6 The Acetoacetic Ester
Synthesis 21.7 The Malonic Ester Synthesis 21.8
Barbiturates 21.9 Michael Additions of Stabilized Anions 21.10 a
Deprotonation of Carbonyl Compounds by Lithium Dialkylamides 21.11
Summary
Problems
Chapter 22 - Amines22.1 Amine Nomenclature 22.2 Structure and Bonding 22.3
Physical Properties 22.4 Basicity of Amines Amines as Natural
Products 22.5 Tetraalkylammonium Salts as Phase-Transfer
Catalysts 22.6 Reactions That Lead to Amines: A Review and a
Preview 22.7 Preparation of Amines by Alkylation of Ammonia 22.8 The Gabriel Synthesis of Primary Alkylamines 22.9 Preparation of Amines
by Reduction 22.10 Reductive Amination 22.11 Reactions of Amines:
A Review and a Preview 22.12 Reaction of Amines with Alkyl
Halides 22.13 The Hofmann Elimination 22.14 Electrophilic Aromatic
Substitution in Arylamines 22.15 Nitrosation of Alkylamines 22.16 Nitrosation of Arylamines 22.17 Synthetic Transformations of Aryl
diazonium Slats 22.18 Azo Coupling
From Dyes to Sulfa Drugs 22.19 Spectroscopic Analysis of Amines 22.20 Summary
Problems
Chapter 23 - Aryl Halides23.1 Bonding in Aryl Halides 23.2 Sources of Aryl
Halides 23.3 Physical Properties of Aryl Halides 23.4 Reactions of
Aryl Halides: A Review and a Preview 23.5 Nucleophilic Substitution in
Nitro-Substituted Aryl Halides 23.6 The Addition-Elimination Mechanism of
Nucleophilic Aromatic Substitution 23.7 Related Nucleophilic Aromatic
Substitution Reactions 23.8 The Elimination-Addition Mechanism of
Nucleophilic Aromatic Substitution: Benzyne 23.9 Diels-Alder Reactions of
Benzyne 23.10 Summary
Problems
Chapter 24 - Phenols24.1 Nomenclature 24.2 Structure and Bonding 24.3 Physical
Properties 24.4 Acidity of Phenols 24.5 Substituent Effects on the
Acidity of Phenols 24.6 Sources of Phenols 24.7 Naturally
Occurring Phenols 24.8 Reactions of Phenols: Electrophilic Aromatic
Substitution 24.9 Acylation of Phenols 24.10 Carboxylation of
Phenols: Aspirin and the Kolbe-Schmitt Reaction 24.11 Preparation of Aryl
Ethers Agent Orange and Dioxin 24.12 Cleavage of Aryl Ethers by
Hydrogen Halides 24.13 Claisen Rearrangement of Allyl Aryl
Ethers 24.14 Oxidation of Phenols: Quinones 24.15 Spectroscopic
Analysis of Phenols 24.16 Summary
Problems
Chapter 25 - Carbohydrates25.1 Classification of Carbohydrates 25.2 Fischer Projections and
D-L Notation 25.3 The Aldotetroses 25.4 Aldopentoses and
Aldohexoses 25.5 A mnemonic for carbohydrate Configurations 25.6
Cyclic Forms of Carbohydrates: Furanose Forms 25.7 Cyclic Forms of
Carbohydrates: Pyranose Forms 25.8 Mutarotation 25.9 Ketoses 25.10 Deoxy Sugars 25.11 Amino Sugars 25.12 Branched-chain Carbohydrates 25.13 Glycosides 25.14 Disaccharides 25.15 Polysaccharides 25.16 Cell-Surface
Glycoproteins How Sweet it is! 25.17 Carbohydrate Structure
Determination 25.18 Reduction of Carbohydrates 25.19 Oxidation of
Carbohydrates 25.20 Cyanohydrin Formation and Chain
Extension 25.21 Epimerizaton, Isomerization, and Retro-Aldol
Cleavage 25.22 Acylation and Alkylation of Hydroxyl Groups in
Carbohydrates 25.23 Periodic Acid Oxidation of Carbohydrates 25.24
Summary
Problems
Chapter 26 - Lipids26.1 Acetyl Coenzyme A 26.2 Fats, Oils, and Fatty
Acids 26.3 Fatty Acid Biosynthesis 26.4 Phospholipids 26.5 Waxes 26.6 Prostaglandins Nonsteroidal
Anti-Inflammatory Drugs (NSAIDs) and COX-2 Inhibitors 26.7 Terpenes: The Iosprene
Rule 26.8 Isopentenyl Pyrophosphate: The Biological Isoprene
Unit 26.9 Carbon-Carbon Bond-Formation in Terpene
Biosynthesis 26.10 The Pathway from Acetate to Isopentenyl
Pyrophosphate 26.11 Steroids: Cholesterol Good Cholesterol? Bad
Cholesterol? What's the Difference? 26.12 Vitamin D 26.13 Bile
Acids 26.14 Corticosteroids 26.15 Sex Hormones Anabolic Steroids 26.16 Carotenoids 26.17 Summary
Problems
Chapter 27 - Amino Acids, Peptides, and
Proteins27.1 Classification of Amino Acids 27.2 Stereochemistry of Amino
Acids 27.3 Acid-Base Behavior of Amino
Acids Electrophoresis 27.4 Synthesis of Amino Acids 27.5 Reactions of Amino Acids 27.6 Some Biochemical Reactions of Amino
Acids 27.7 Peptides 27.8 Introduction to Peptide Structure
Determination 27.9 Amino Acid Analysis 27.10 Partial Hydrolysis of
Peptides 27.11 End Group Analysis 27.12 Insulin 27.13 The
Edman Degradation and Automated Sequencing of Peptides 27.14 The Strategy
of Peptide Synthesis 27.15 Amino Group Protection 27.16 Carboxyl
Group Protection 27.17 Peptide Bond Formation 27.18 Solid-Phase
Peptide Synthesis: The Merrifield Method 27.19 Secondary Structures of
Peptides and Proteins 27.20 Tertiary Structure of Peptides and
Proteins 27.21 Coenzymes 27.22 Protein Quaternary Structure:
Hemoglobin 27.23 Summary
Problems
Chapter 28 - Nucleosides, Nucleotides, and
Nucleic Acids 28.1 Pyrimidines and Purines 28.2 Nucleosides 28.3
Nucleotides 28.4 Bioenergetics 28.5 ATP and
Bioenergetics 28.6 Phosphodiesters, Oligonucleotides, and
Polynucleotides 28.7 Nucleic Acids
"It has not escaped our notice…" 28.8 Secondary Structure of DNA. The Double Helix 28.9
Tertiary Structure of DNA. Supercoils 28.10 Replication of
DNA 28.11 Ribonucleic Acids 28.12 Protein Synthesis RNA
World 28.13 AIDS 28.14 DNA Sequencing 28.15 The Human
Genome Project 28.16 DNA Profiling and the Polymerase Chain Reaction
(PCR) 28.17 Summary
Problems
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