Organic Chemistry [平装]

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		Organic Chemistry [平装]
		Organic Chemistry [平装]

作者简介

Paula Yurkanis Bruice was raised primarily in Massachusetts, Germany, and Switzerland and was graduated from the Girls' Latin School in Boston. She received an A.B. from Mount Holyoke College and a Ph.D. in chemistry from the University of Virginia. She received an NIH postdoctoral fellowship for study in biochemistry at the University of Virginia Medical School, and she held a postdoctoral appointment in the Department of Pharmacology at Yale Medical School. She is a member of the faculty at the University of California, Santa Barbara, where she has received the Associated Students Teacher of the Year Award, the Academic Senate Distinguished Teaching Award, and two Mortar Board Professor of the Year Awards. Her research interests concern the mechanism and catalysis of organic reactions, particularly those of biological significance. Paula has a daughter and a son who are physicians and a son who is a lawyer. Her main hobbies are reading mystery/suspense novels and her pets (three dogs, two cats, and a parrot).

目录

I AN INTRODUCTION TO THE STUDY OF CHEMISTRY 1 Electronic Structure and Bonding * Acids and Bases 1.1 The Structure of an Atom 1.2 How Electrons in an Atom are Distributed 1.3 Ionic and Covalent Bonds 1.4 How the Structure of a Compound is Represented 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 1.9 How a Triple Bond is Formed: The Bonds in Ethyne 1.10 Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion 1.11 The Bonds in Water 1.12 The Bonds in Ammonia and in the Ammonium Ion 1.13 The Bond in a Hydrogen Halide 1.14 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles 1.15 The Dipole Moments of Molecules 1.16 An Introduction to Acids and Bases 1.17 pka and pH 1.18 Organic Acids and Bases 1.19 How to Predict the Outcome of an Acid-Base Reaction 1.20 How to Determine the Position of Equilibrium 1.21 How the Structure of an Acid Affects its pka Value 1.22 How Substituents Affect the Strength of an Acid 1.23 An Introduction to Delocalized Electrons 1.24 A Summary of the Factors that Determine Acid Strength 1.25 How pH Affects the Structure of an Organic Compound 1.26 Buffer Solutions 1.27 Lewis Acids and Bases 2 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure 2.1 How Alkyl Substituents Are Named 2.2 The Nomenclature of Alkanes 2.3 The Nomenclature of Cycloalkanes * Skeletal Structures 2.4 The Nomenclature of Alkyl Halides 2.5 The Nomenclature of Ethers 2.6 The Nomenclature of Alcohols 2.7 The Nomenclature of Amines 2.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines 2.9 The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines 2.10 Rotation Occurs About Carbon-Carbon Single Bonds 2.11 Some Cycloalkanes Have Angle Strain 2.12 Conformers of Cyclohexane 2.13 Conformers of Monosubstituted Cyclohexanes 2.14 Conformers of Disubstituted Cyclohexanes 2.15 Fused Cyclohexane Rings II ELECTROPHILIC ADDITION REACTIONS, STEREOCHEMISTRY, AND ELECTRON DELOCALIZATION 3 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity * Thermodynamics and Kinetics 3.1 Molecular Formulas and the Degree of Unsaturation 3.2 The Nomenclature of Alkenes 3.3 The Structures of Alkenes 3.4 Alkenes Can Have Cis and Trans Isomers 3.5 Naming Alkenes Using the E,Z System 3.6 How Alkenes React * Curved Arrows Show the Flow of Electrons 3.7 Thermodynamics and Kinetics 3.8 The Rate of a Reaction and the Rate Constant for a Reaction 3.9 A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a Reaction 4 The Reactions of Alkenes 4.1 The Addition of a Hydrogen Halide to an Alkene 4.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon 4.3 What Does the Structure of the Transition State Look Like? 4.4 Electrophilic Addition Reactions Are Regioselective 4.5 The Addition of Water to an Alkene 4.6 The Addition of an Alcohol to an Alkene 4.7 A Carbocation Will Rearrange If It Can Form a More Stable Carbocation 4.8 The Addition of a Halogen to an Alkene 4.9 Oxymercuration-Reduction and Alkoxymercuration-Reduction Are Other Ways to Add Water or an Alcohol to an Alkene 4.10 The Addition of a Peroxyacid to an Alkene 4.11 The Addition of Borane to an Alkene: Hydroboration-Oxidation 4.12 The Addition of Hydrogen to an Alkene 4.13 The Relative Stabilities of Alkenes 4.14 Reactions and Synthesis 5 Stereochemistry: The Arrangement of Atoms in Space; The Stereochemistry of Addition Reactions 5.1 Cis-Trans Isomers Result from Restricted Rotation 5.2 A Chiral Object Has a Nonsuperimposable Mirror Image 5.3 An Asymmetric Center Is a Cause of Chirality in a Molecule 5.4 Isomers with One Asymmetric Center 5.5 Asymmetric Centers and Stereocenters 5.6 How to Draw Enantiomers 5.7 Naming Enantiomers by the R,S System 5.8 Chiral Compounds Are Optically Active 5.9 How Specific Rotation is Measured 5.10 Enantiomeric Excess 5.11 Isomers with More than One Asymmetric Center 5.12 Meso Compounds Have Asymmetric Centers but Are Optically Inactive 5.13 How to Name Isomers with More than One Asymmetric Center 5.14 Reactions of Compounds that Contain an Asymmetric Center 5.15 Using Reactions that Do Not Break Bonds to an Asymmetric Center to Determine Relative Configurations 5.16 How Enantiomers Can Be Separated 5.17 Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers 5.18 Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions 5.19 The Stereochemistry of Electrophilic addition Reactions of Alkenes 5.20 The Stereochemistry of Enzyme-Catalyzed Reactions 5.21 Enantiomers Can Be Distinguished by Biological Molecules 6 The Reactions of Alkynes: An Introduction to Multistep Synthesis 6.1 The Nomenclature of Alkynes 6.2 How to Name a Compound That Has More than One Functional Group 6.3 The Physical Properties of Unsaturated Hydrocarbons 6.4 The Structure of Alkynes 6.5 How Alkynes React 6.6 The Addition of Hydrogen Halides and Addition of Halogens to an Alkyne 6.7 The Addition of Water to an Alkyne 6.8 The Addition of Borane to an Alkyne: Hydroboration-Oxidation 6.9 The Addition if Hydrogen to an Alkyne 6.10 A Hydrogen Bonded to an sp Carbon is "Acidic" 6.11 Synthesis Using Acetylide Ions 6.12 Designing a Synthesis I: An Introduction to Multistep Synthesis 7 Delocalized Electrons and Their Effect on Stability, Reactivity, and pKa * More About Molecular Orbital Theory 7.1 Delocalized Electrons Explain Benzene's Structure 7.2 The Bonding in Benzene 7.3 Resonance Contributors and the Resonance Hybrid 7.4 How to Draw Resonance Contributors 7.5 The Predicted Stabilities of Resonance Contributors 7.6 Delocalized Energy Is the Additional Stability Delocalized Electrons Give to a Compound 7.7 Examples That Show How Delocalized Electrons Affect Stability 7.8 A Molecular Orbital Description of Stability 7.9 How Delocalized Electrons Affect pKa Values 7.10 Delocalized Electrons Can Affect the Product of a Reaction 7.11 Thermodynamic Versus Kinetic Control of Reactions 7.12 The Diels-Adler Reaction Is a 1,4-Addition Reaction III SUBSTITUTION AND ELIMINATION REACTIONS 8 Substitution Reactions of Alkyl Halides 8.1 The Mechanism For an SN2 Reaction 8.2 Factors That Affect SN2 Reactions 8.3 The Reversibility of an SN2 Reaction Depends on the Basicities of the Leaving Groups in the Forward and Reverse Directions 8.4 The Mechanism for an SN1 Reaction 8.5 Factors That Affect SN1 Reactions 8.6 More About the Stereochemistry of SN2 and SN1Reactions 8.7 Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides 8.8 Competition Between SN2 and SN1Reactions 8.9 The Role of the Solvent in SN2 and SN1 Reactions 8.10 Intermolecular Versus Intramolecular Reactions 8.11 Biological Methylating Reagents Have Good Leaving Groups 9 Elimination Reactions of Alkyl Halides * Competition between Substitution and Elimination 9.1 The E2 Reaction 9.2 An E2 Reaction is Regioselective 9.3 The E1 Reaction 9.4 Competition between E2 and E1 Reactions 9.5 E2 and E1 Reactions are Stereoselective 9.6 Elimination from Substituted Cyclohexanes 9.7 A Kinetic Isotope Effect Can Help Determine a Mechanism 9.8 Competition between Substitution and Elimination 9.9 Substitution and Elimination Reactions in Synthesis 9.10 Designing a Synthesis II: Approaching the Problem 10 Reactions of Alcohols, Ethers, Epoxides, Amine, and Sulfur- Containing Compounds 10.1 Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides 10.2 Other Methods Used to Convert Alcohols into Alkyl Halides 10.3 Converting an Alcohol to a Sulfonate Ester 10.4 Elimination Reactions of Alcohols: Dehydration 10.5 Oxidation of Alcohols 10.6 Nucleophilic Substitution Reactions of Ethers 10.7 Nucleophilic Substitution Reactions of Epoxides 10.8 Amines Do Not Undergo Substitution or Elimination Reactions 10.9 Quaternary Ammonium Hydroxides Undergo Elimination Reactions 10.10 Phase-Transfer Catalysts 10.11 Thiols, Sulfides, and Sulfonium Salts 11 Organometallic Compounds 11.1 Organolithium and Organomagnesium Compounds 11.2 The Reaction Organolithium Compounds and Grighard Reagents with Electrophiles 11.3 Transmetallation 11.4 Coupling Reactions 11.5 Palladium-Catalyzed Coupling Reactions 11.6 Alkene Metathesis 12 Radicals * Reactions of Alkanes 12.1 Alkanes Are Unreactive Compounds 12.2 Chlorination and Bromination of Alkanes 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 12.6 Formation of Explosive Peroxides 12.7 The Addition of Radicals to an Alkene 12.8 The Stereochemistry of Radical Substitution and Addition Reactions 12.9 Radical Substitution of Benzylic and Allylic Hydrogens 12.10 Designing a Synthesis III: More Practice with Multistep Synthesis 12.11 Radical Reactions Occur in Biological Systems 12.12 Radicals and Stratospheric Ozone IV IDENTIFICATION OF ORGANIC COMPOUNDS 13 Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/Visible Spectroscopy 13.1 Mass Spectrometry 13.2 The Mass Spectrum * Fragmentation 13.3 Isotopes in Mass Spectrometry 13.4 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas 13.5 Fragmentation Patterns of Functional Groups 13.6 Other Ionization Methods 13.7 Spectroscopy and the Electromagnetic Spectrum 13.8 Infrared Spectroscopy 13.9 Characteristic Infrared Absorption Bands 13.10 The Intensity of Absorption Bands 13.11 The Position of Absorption Bands 13.12 The Position of an Absorption Band is Affected by Electron Delocalization, Election Donation and Withdrawal, and Hydrogen Bonding 13.13 The Shape of Absorption Bands 13.14 The Absence of Absorption Bands 13.15 Some Vibrations Are Infrared Inactive 13.16 How to Interpret An Infrared Spectrum 13.17 Ultraviolet and Visible Spectroscopy 13.18 The ...

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