Organic chemistry

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Organic chemistry / Maitland Jones, Jr

版:: 3rd ed
資料種別:: 図書
出版情報:: New York : W.W. Norton, c2005
形態:: xxxvi, 1323, 62 p. ; 27 cm. + 1 CD-ROM (4 3/4 in.)
著者名:: Jones, Maitland, 1937- <DA03096174>
ISBN:: 9780393924084 [0393924084]
9780393114058 [0393114058] (: hbk)
書誌ID:: BA67768651

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他の版・巻

Organic chemistry. 5th ed (: hardcover ; International student ed. : pbk ; : pbk)
Maitland Jones, Jr., Steven A. Fleming , W.W. Norton & Company , c2014

Organic chemistry. 4th ed (international student ed. ; : CD-ROM)
Maitland Jones, Jr, Steven A. Fleming , W.W. Norton , c2010

書誌詳細

注記:

Includes index

主題:

Chemistry, Organic

言語:

英語

目次情報:

Preface

Introduction

Atoms and Molecules; Orbitals and Bonding / Chapter 1.：

Atoms and Atomic Orbitals / 1.1：

Covalent Bonds and Lewis Structures / 1.2：

Introduction to Resonance Forms / 1.3：

More on Atomic Orbitals / 1.4：

The Covalent Bond: Hydrogen (H[subscript 2]) / 1.5：

Bond Strength / 1.6：

An Introduction to Reactivity: Acids and Bases / 1.7：

Quantum Mechanics and Babies / 1.8：

Summary / 1.9：

Additional Problems / 1.10：

Alkanes / Chapter 2.：

The Structure of Methane (CH[subscript 4]) / 2.1：

Hybrid Orbitals: Making a Better Model for Methane / 2.2：

Derivatives of Methane: Methyl (CH[subscript 3]) and Methyl Compounds (CH[subscript 3]X) / 2.3：

The Methyl Cation ([superscript +]CH[subscript 3]), Anion ([superscript -]:CH[subscript 3]), and Radical (.CH[subscript 3]) / 2.4：

Ethane (C[subscript 2]H[subscript 6]), Ethyl Compounds (C[subscript 2]H[subscript 5]X), and Newman Projections / 2.5：

Structure Drawings / 2.6：

Propane (C[subscript 3]H[subscript 8]) and Propyl Compounds (C[subscript 3]H[subscript 7]X) / 2.7：

Butanes (C[subscript 4]H[subscript 10]), Butyl Compounds (C[subscript 4]H[subscript 9]X), and Conformational Analysis / 2.8：

Pentanes (C[subscript 5]H[subscript 12]) and Pentyl Compounds (C[subscript 5]H[subscript 11]X) / 2.9：

The Naming Conventions for Alkanes / 2.10：

Writing Isomers / 2.11：

Rings / 2.12：

Physical Properties of Alkanes and Cycloalkanes / 2.13：

[superscript 13]C Nuclear Magnetic Resonance Spectroscopy / 2.14：

Alkanes as Biomolecules / 2.15：

Alkenes and Alkynes / 2.16：

Alkenes: Structure and Bonding / 3.1：

Derivatives, Isomers, and Names of Alkenes / 3.2：

Nomenclature / 3.3：

The Cahn-Ingold-Prelog Priority System / 3.4：

Relative Stability of Alkenes: Heats of Formation / 3.5：

Double Bonds in Rings / 3.6：

Physical Properties of Alkenes / 3.7：

Alkynes: Structure and Bonding / 3.8：

Relative Stability of Alkynes: Heats of Formation / 3.9：

Derivatives and Isomers of Alkynes / 3.10：

Triple Bonds in Rings / 3.11：

Physical Properties of Alkynes / 3.12：

Acidity of Alkynes / 3.13：

Molecular Formulas and Degrees of Unsaturation / 3.14：

Alkenes and Biology / 3.15：

Stereochemistry / 3.16：

Chirality / 4.1：

Properties of Enantiomers: Physical Differences / 4.2：

The (R/S) Convention / 4.3：

The Physical Basis of Optical Activity / 4.4：

Properties of Enantiomers: Chemical Differences / 4.5：

Interconversion of Enantiomers by Mobile Equilibria: Gauche Butane / 4.6：

Diastereomers: Molecules Containing More Than One Stereogenic Atom / 4.7：

Physical Properties of Diastereomers: Optical Resolution / 4.8：

Determination of Absolute Configuration (R or S) / 4.9：

Stereochemical Analysis of Ring Compounds (a Beginning) / 4.10：

Review of Isomerism / 4.11：

Chirality without "Four Different Groups Attached to One Carbon" / 4.12：

Stereochemistry in the Real World: Thalidomide; The Consequences of Being Wrong-Handed / 4.13：

Rings and Strain / 4.14：

Quantitative Evaluation of Strain Energy / 5.2：

Stereochemistry of Cyclohexane: Conformational Analysis / 5.3：

Monosubstituted Cyclohexanes / 5.4：

Disubstituted Ring Compounds / 5.5：

Bicyclic Compounds / 5.6：

Polycyclic Systems / 5.7：

Adamantanes in Materials and Biology / 5.8：

Substitution and Elimination Reactions: The S[subscript N]2, S[subscript N]1, E2, and E1 Reactions / 5.9：

Alkyl Halides: Nomenclature and Structure / 6.1：

Reaction Mechanism: Br[o slash]nsted Acids and Bases / 6.2：

The Arrow Formalism / 6.3：

Lewis Acids and Bases / 6.4：

HOMO-LUMO Interactions / 6.5：

Reactions of Alkyl Halides: The Substitution Reaction / 6.6：

Substitution, Nucleophilic, Bimolecular: The S[subscript N]2 Reaction / 6.7：

The S[subscript N]2 Reaction in Biochemistry / 6.8：

Substitution, Nucleophilic, Unimolecular: The S[subscript N]1 Reaction / 6.9：

Overview of the S[subscript N]2 and S[subscript N]1 Reactions / 6.10：

The Unimolecular Elimination Reaction: E1 / 6.11：

The Bimolecular Elimination Reaction: E2 / 6.12：

What Can We Do with These Reactions? Synthetic Utility / 6.13：

Equilibria / 6.14：

Equilibrium / 7.1：

Gibbs Standard Free Energy Change / 7.2：

Rates of Chemical Reactions / 7.3：

Rate Constant / 7.4：

Energy Barriers in Chemical Reactions: The Transition State and Activation Energy / 7.5：

Reaction Mechanism / 7.6：

The Hammond Postulate: Thermodynamics versus Kinetics / 7.7：

Enzymes and Reaction Rates / 7.8：

Additions to Alkenes 1 / 7.9：

Electronegativity / 8.1：

Mechanism of the Addition of Hydrogen Halides to Alkenes / 8.2：

Regiochemistry / 8.3：

Resonance Effects / 8.4：

Review of Resonance: How to Write Resonance Forms / 8.5：

Resonance and the Stability of Carbocations / 8.6：

Inductive Effects on Addition Reactions / 8.7：

H--X Addition Reactions: Hydration / 8.8：

Dimerization and Polymerization of Alkenes / 8.9：

Hydroboration / 8.10：

Utility of Hydroboration: Alcohol Formation / 8.11：

Rearrangements During H--X Addition to Alkenes / 8.12：

Rearrangements in Biological Processes / 8.13：

Additions to Alkenes 2; Additions to Alkynes / 8.14：

Addition of X[subscript 2] Reagents / 9.1：

Hydration Through Mercury Compounds: Oxymercuration / 9.2：

Other Addition Reactions Involving Three-Membered Rings: Oxiranes and Cyclopropanes / 9.3：

Dipolar Addition Reactions / 9.4：

Addition Reactions of Alkynes: H--X Addition / 9.5：

Addition of X[subscript 2] Reagents to Alkynes / 9.6：

Hydration of Alkynes / 9.7：

Hydroboration of Alkynes / 9.8：

Hydrogenation of Alkynes: Syn Hydrogenation / 9.9：

Reduction by Sodium in Ammonia: Anti Hydrogenation / 9.10：

Three-membered Rings in Biochemistry / 9.11：

Radical Reactions / 9.12：

Formation and Simple Reactions of Radicals / 10.1：

Structure of Radicals / 10.2：

Stability of Radicals / 10.3：

Radical Addition to Alkenes / 10.4：

Other Radical Addition Reactions / 10.5：

Radical-Initiated Addition of HBr to Alkynes / 10.6：

Photohalogenation / 10.7：

Allylic Halogenation / 10.8：

Rearrangements (and Nonrearrangements) of Radicals / 10.9：

Radicals in Your Body: Do Free Radicals Age Us? / 10.10：

Dienes and the Allyl System; 2p Orbitals in Conjugation / 10.11：

Allenes: 1,2-Dienes / 11.1：

Related Systems: Ketenes and Cumulenes / 11.2：

Allenes as Intermediates in the Isomerization of Acetylenes / 11.3：

1,3-Dienes / 11.4：

The Physical Consequences of Conjugation / 11.5：

Molecular Orbitals and Ultraviolet Spectroscopy / 11.6：

Polyenes and Vision / 11.7：

The Chemical Consequences of Conjugation: Addition Reactions of Dienes / 11.8：

Thermodynamic and Kinetic Control of Addition Reactions / 11.9：

The Allyl System: Three Overlapping 2p Orbitals / 11.10：

The Allyl Cation: S[subscript N]1 Solvolysis of Allylic Halides / 11.11：

S[subscript N]2 Reactions of Allylic Halides / 11.12：

The Allyl Radical / 11.13：

The Allyl Anion / 11.14：

The Diels-Alder Reaction of Dienes / 11.15：

Biosynthesis of Terpenes / 11.16：

Steroid Biosynthesis / 11.17：

Conjugation and Aromaticity / 11.18：

The Structure of Benzene / 12.1：

A Resonance Picture of Benzene / 12.2：

The Molecular Orbital Picture of Benzene / 12.3：

Quantitative Evaluations of Resonance Stabilization (Delocalization Energy) in Benzene / 12.4：

A Generalization of Aromaticity: Huckel's 4n + 2 Rule / 12.5：

Annulenes / 12.6：

Substituted Benzenes / 12.7：

Physical Properties of Substituted Benzenes / 12.8：

Heterobenzenes and other Heterocyclic Aromatic Compounds / 12.9：

Polynuclear Aromatic Compounds / 12.10：

Introduction to the Chemistry of Benzene / 12.11：

The Benzyl Group and Its Reactivity: Activation of the Adjacent (Benzyl) Position by Benzene Rings / 12.12：

The Bio-downside: The Mechanism of Carcinogenesis by Polycyclic Aromatic Compounds / 12.13：

Substitution Reactions of Aromatic Compounds / 12.14：

Addition Reactions of Benzenes to Give Nonaromatic Compounds: Hydrogenation / 13.1：

Diels-Alder Reactions / 13.2：

Other Addition Reactions / 13.3：

Substitution Reactions of Benzene / 13.4：

Electrophilic Aromatic Substitution / 13.5：

The Friedel-Crafts Alkylation Reaction / 13.6：

Friedel-Crafts Acylation / 13.7：

Stable Carbocations in "Superacid" / 13.8：

Summary of Simple Aromatic Substitution: What We Can Do So Far / 13.9：

Disubstituted Benzenes: Ortho, Meta, and Para Substitution / 13.10：

Inductive Effects in Aromatic Substitution / 13.11：

Polysubstitution of Aromatic Compounds and Synthesis of Multiply Substituted Benzenes / 13.12：

Nucleophilic Aromatic Substitution / 13.13：

Benzyne / 13.14：

Biological Synthesis of Aromatic Rings: Phenylalanine / 13.15：

Analytical Chemistry / 13.16：

Chromatography / 14.1：

Mass Spectrometry / 14.2：

Infrared Spectroscopy / 14.3：

Nuclear Magnetic Resonance Spectroscopy / 14.4：

Survey of NMR Spectra of Organic Molecules / 14.5：

Spin-Spin Coupling: The Coupling Constant, J / 14.6：

More Complicated Spectra / 14.7：

Decoupled Spectra / 14.8：

Nuclear Magnetic Resonance Spectra of Other Nuclei / 14.9：

Determination of the Structure of a Complex Biomolecule: Maitotoxin / 14.10：

Dynamic NMR / 14.11：

Carbonyl Chemistry 1: Addition Reactions / 14.12：

Structure of the Carbon-Oxygen Double Bond / 15.1：

Nomenclature of Carbonyl Compounds / 15.2：

Physical Properties of Carbonyl Compounds / 15.3：

Spectroscopy of Carbonyl Compounds / 15.4：

Reactions of Carbonyl Compounds: Simple Reversible Additions / 15.5：

Equilibrium in Addition Reactions / 15.6：

Other Addition Reactions: Additions of Cyanide and Bisulfite / 15.7：

Addition Reactions Followed by Water Loss: Acetal and Ketal Formation / 15.8：

Addition Reactions of Nitrogen Bases: Imine and Enamine Formation / 15.9：

Organometallic Reagents / 15.10：

Irreversible Addition Reactions / 15.11：

Oxidation of Alcohols to Carbonyl Compounds / 15.12：

The Wittig Reaction / 15.13：

Biological Oxidation / 15.14：

The Chemistry of Alcohols Summarized and Extended: Glycols, Ethers, and Related Sulfur Compounds / 15.15：

Structure of Alcohols / 16.1：

Physical Properties of Alcohols / 16.3：

Spectroscopic Properties of Alcohols / 16.4：

Acid and Base Properties of Alcohols / 16.5：

Reactions of Alcohols / 16.6：

Syntheses of Alcohols / 16.7：

Dialcohols: Diols or Glycols / 16.8：

Ethers / 16.9：

Syntheses of Ethers / 16.10：

Reactions of Ethers / 16.11：

Thiols (Mercaptans) and Thioethers (Sulfides) / 16.12：

Reactions and Syntheses of Thiols and Sulfides / 16.13：

Crown Ethers / 16.14：

Carbonyl Chemistry 2: Reactions at the [alpha]-Position / 16.15：

Aldehydes and Ketones Are Weak Bronsted Acids / 17.1：

Reactions of Enols and Enolates / 17.2：

Condensation Reactions of Carbonyl Compounds: The Aldol Condensation / 17.3：

Reactions Related to the Aldol Condensation / 17.4：

Problem Solving / 17.5：

Carbonyl Compounds without [alpha]-Hydrogens: Magid's Third Rule / 17.6：

The Aldol Condensation in the Real World: Introduction to Modern Synthesis / 17.7：

Carboxylic Acids / 17.8：

Nomenclature and Properties of Carboxylic Acids / 18.1：

Structure of Carboxylic Acids / 18.2：

Infrared and Nuclear Magnetic Resonance Spectra of Carboxylic Acids / 18.3：

Acidity and Basicity of Carboxylic Acids / 18.4：

Reactions of Carboxylic Acids / 18.5：

Reactivity of Carboxylic Acids at the [alpha]-Position / 18.6：

Syntheses of Carboxylic Acids / 18.7：

Fatty Acids / 18.8：

Derivatives of Carboxylic Acids: Acyl Compounds / 18.9：

Physical Properties and Structures of Acyl Compounds / 19.1：

Spectral Characteristics / 19.3：

Reactions of Acid Chlorides / 19.4：

Reactions of Anhydrides / 19.5：

Addition-Elimination Reactions of Esters / 19.6：

Reactions of Amides / 19.7：

Reactions of Nitriles / 19.8：

Reactions of Ketenes / 19.9：

Enolate Chemistry of Esters: The Claisen and Related Condensation Reactions / 19.10：

Variations on the Claisen Condensation / 19.11：

Forward and Reverse Claisen Condensations in Biology / 19.12：

Reactions of [beta]-Keto Esters / 19.13：

Complicated "Fun in Base" Problems / 19.14：

New Synthetic Routes to Acyl Compounds / 19.15：

Thermal Elimination Reactions of Esters / 19.16：

Introduction to the Chemistry of Nitrogen-Containing Compounds: Amines / 19.17：

Structure and Physical Properties of Amines / 20.1：

Spectroscopic Properties of Amines / 20.3：

Acid and Base Properties of Amines / 20.4：

Reactions of Amines / 20.5：

Syntheses of Amines / 20.6：

Alkaloids / 20.7：

Synthesis of Quinine / 20.8：

Phase-Transfer Catalysis: Ammonium Ions in Synthesis / 20.9：

Aromatic Transition States: Orbital Symmetry / 20.10：

Concerted Reactions / 21.1：

Electrocyclic Reactions / 21.2：

Cycloaddition Reactions / 21.3：

Sigmatropic Shift Reactions / 21.4：

Sigmatropic Shifts of Carbon / 21.5：

Other Sigmatropic Shifts / 21.6：

A Biological Cope Rearrangement / 21.7：

A Molecule with a Fluxional Structure / 21.8：

Introduction to Polyfunctional Compounds: Intramolecular Reactions and Neighboring Group Participation / 21.9：

Heteroatoms as Neighboring Groups / 22.1：

Neighboring [pi] Systems / 22.2：

Single Bonds as Neighboring Groups / 22.3：

Coates' Cation / 22.4：

A Family of Concerted Rearrangements of Acyl Compounds / 22.5：

Polyfunctional Natural Products: Carbohydrates / 22.6：

Nomenclature and Structure / 23.1：

Reactions of Sugars / 23.2：

The Ring Size in Glucose / 23.3：

The Fischer Determination of the Structure of D-Glucose (and the 15 Other Aldohexoses) / 23.4：

An Introduction to Di- and Polysaccharides / 23.5：

Introduction to the Chemistry of Heterocyclic Molecules / 23.6：

Three-Membered Heterocycles: Oxiranes (Epoxides), Thiiranes (Episulfides), and Aziridines / 24.1：

Four-Membered Heterocycles: Oxetanes, Thietanes, and Azetidines / 24.2：

Five- and Six-Membered Heterocycles / 24.3：

Nonaromatic Heterocycles Containing More Than One Heteroatom / 24.4：

Nitrogen-Containing Aromatic Heterocyclic Compounds / 24.5：

Other Aromatic Heterocycles: Furan and Thiophene / 24.6：

Aromatic Heterocycles Containing More Than One Heteroatom / 24.7：

Two-Ring Heterocycles / 24.8：

Bioactive Heterocycles: Penicillin and Related Antibiotics / 24.9：

Introduction to Amino Acids and Polyamino Acids (Peptides and Proteins) / 24.10：

Amino Acids / 25.1：

Reactions of Amino Acids / 25.2：

Peptide Chemistry / 25.3：

Nucleosides, Nucleotides, and Nucleic Acids / 25.4：

Key Terms / 25.5：

Some Commonly Used Abbreviations

Index

Preface

Introduction

Atoms and Molecules; Orbitals and Bonding / Chapter 1.：

Atoms and Atomic Orbitals / 1.1：

Covalent Bonds and Lewis Structures / 1.2：

Introduction to Resonance Forms / 1.3：

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