Efnisyfirlit

• Cover Page
• Title Page
• Copyright Page
• About the Authors
• Contents in Brief
• Contents
• Preface
• Acknowledgments
• Prologue
  • What Is Organic Chemistry?
  • Some Representative Organic Molecules
  • Marine Natural Products
• 1 Structure and Bonding
  • 1.1 The Periodic Table
  • 1.2 Bonding
  • 1.3 Lewis Structures
  • 1.4 Isomers
  • 1.5 Exceptions to the Octet Rule
  • 1.6 Resonance 18
  • 1.7 Determining Molecular Shape
  • 1.8 Drawing Organic Structures
  • 1.9 Hybridization
  • 1.10 Ethane, Ethylene, and Acetylene
  • 1.11 Bond Length and Bond Strength
  • 1.12 Electronegativity and Bond Polarity
  • 1.13 Polarity of Molecules
  • 1.14 Oxybenzone—A Representative Organic Molecule
  • Chapter Review
  • Problems
• 2 Acids and Bases
  • 2.1 Brønsted–Lowry Acids and Bases
  • 2.2 Reactions of Brønsted–Lowry Acids and Bases
  • 2.3 Acid Strength and pKa
  • 2.4 Predicting the Outcome of Acid–Base Reactions
  • 2.5 Factors That Determine Acid Strength
  • 2.6 Common Acids and Bases
  • 2.7 Aspirin
  • 2.8 Lewis Acids and Bases
  • Chapter Review
  • Problems
• 3 Introduction to Organic Molecules and Functional Groups
  • 3.1 Functional Groups
  • 3.2 An Overview of Functional Groups
  • 3.3 Intermolecular Forces
  • 3.4 Physical Properties
  • 3.5 Application: Vitamins
  • 3.6 Application of Solubility: Soap
  • 3.7 Application: The Cell Membrane
  • 3.8 Functional Groups and Reactivity
  • 3.9 Biomolecules
  • Chapter Review
  • Problems
• 4 Alkanes
  • 4.1 Alkanes—An Introduction
  • 4.2 Cycloalkanes
  • 4.3 An Introduction to Nomenclature
  • 4.4 Naming Alkanes
  • 4.5 Naming Cycloalkanes
  • 4.6 Common Names
  • 4.7 Natural Occurrence of Alkanes
  • 4.8 Properties of Alkanes
  • 4.9 Conformations of Acyclic Alkanes—Ethane
  • 4.10 Conformations of Butane
  • 4.11 An Introduction to Cycloalkanes
  • 4.12 Cyclohexane
  • 4.13 Substituted Cycloalkanes
  • 4.14 Oxidation of Alkanes
  • Chapter Review
  • Problems
• 5 Stereochemistry
  • 5.1 Starch and Cellulose
  • 5.2 The Two Major Classes of Isomers
  • 5.3 Looking Glass Chemistry—Chiral and Achiral Molecules
  • 5.4 Stereogenic Centers
  • 5.5 Stereogenic Centers in Cyclic Compounds
  • 5.6 Labeling Stereogenic Centers with Ror S
  • 5.7 Diastereomers
  • 5.8 Meso Compounds
  • 5.9Rand SAssignments in Compounds with Two or More Stereogenic Centers
  • 5.10 Disubstituted Cycloalkanes
  • 5.11 Isomers—A Summary
  • 5.12 Physical Properties of Stereoisomers
  • 5.13 Chemical Properties of Enantiomers
  • Chapter Review
  • Problems
• 6 Understanding Organic Reactions
  • 6.1 Writing Equations for Organic Reactions
  • 6.2 Kinds of Organic Reactions
  • 6.3 Bond Breaking and Bond Making
  • 6.4 Bond Dissociation Energy
  • 6.5 Thermodynamics
  • 6.6 Enthalpy and Entropy
  • 6.7 Energy Diagrams
  • 6.8 Energy Diagram for a Two-Step Reaction Mechanism
  • 6.9 Kinetics
  • 6.10 Catalysts
  • 6.11 Enzymes
  • Chapter Review
  • Problems
• 7 Alkyl Halides and Nucleophilic Substitution
  • 7.1 Introduction to Alkyl Halides
  • 7.2 Nomenclature
  • 7.3 Properties of Alkyl Halides
  • 7.4 Interesting Alkyl Halides
  • 7.5 The Polar Carbon–Halogen Bond
  • 7.6 General Features of Nucleophilic Substitution
  • 7.7 The Leaving Group
  • 7.8 The Nucleophile
  • 7.9 Possible Mechanisms for Nucleophilic Substitution
  • 7.10 Two Mechanisms for Nucleophilic Substitution
  • 7.11 The SN2 Mechanism
  • 7.12 The SN1 Mechanism
  • 7.13 Carbocation Stability
  • 7.14 The Hammond Postulate
  • 7.15 When Is the Mechanism SN1 or SN2?
  • 7.16 Biological Nucleophilic Substitution
  • 7.17 Vinyl Halides and Aryl Halides
  • 7.18 Organic Synthesis
  • Chapter Review
  • Problems
• 8 Alkyl Halides and Elimination Reactions
  • 8.1 General Features of Elimination
  • 8.2 Alkenes—The Products of Elimination Reactions
  • 8.3 The Mechanisms of Elimination
  • 8.4 The E2 Mechanism
  • 8.5 The Zaitsev Rule
  • 8.6 The E1 Mechanism
  • 8.7 SN1and E1 Reactions
  • 8.8 Stereochemistry of the E2 Reaction
  • 8.9 When Is the Mechanism E1 or E2?
  • 8.10 E2 Reactions and Alkyne Synthesis
  • 8.11 When Is the Reaction SN1, SN2, E1, or E2?
  • Chapter Review
  • Problems
• 9 Alcohols, Ethers, and Related Compounds
  • 9.1 Introduction
  • 9.2 Structure and Bonding
  • 9.3 Nomenclature
  • 9.4 Properties of Alcohols, Ethers, and Epoxides
  • 9.5 Interesting Alcohols, Ethers, and Epoxides
  • 9.6 Preparation of Alcohols, Ethers, and Epoxides
  • 9.7 General Features—Reactions of Alcohols, Ethers, and Epoxides
  • 9.8 Dehydration of Alcohols to Alkenes
  • 9.9 Carbocation Rearrangements
  • 9.10 Dehydration Using POCl3and Pyridine
  • 9.11 Conversion of Alcohols to Alkyl Halides with HX
  • 9.12 Conversion of Alcohols to Alkyl Halides with SOCl2and PBr
  • 9.13 Tosylate—Another Good Leaving Group
  • 9.14 Reaction of Ethers with Strong Acid
  • 9.15 Thiols and Sulfides
  • 9.16 Reactions of Epoxides
  • 9.17 Application: Epoxides, Leukotrienes, and Asthma
  • Chapter Review
  • Problems
• 10 Alkenes and Alkynes
  • 10.1 Introduction
  • 10.2 Calculating Degrees of Unsaturation
  • 10.3 Nomenclature
  • 10.4 Properties of Alkenes and Alkynes
  • 10.5 Interesting Alkenes and Alkynes
  • 10.6 Fatty Acids and Triacylglycerols
  • 10.7 Preparation of Alkenes and Alkynes
  • 10.8 Introduction to the Reactions of Alkenes and Alkynes
  • 10.9 Hydrohalogenation—Electrophilic Addition of HX to Alkenes
  • 10.10 Markovnikov’s Rule
  • 10.11 Stereochemistry of Electrophilic Addition of HX
  • 10.12 Hydration—Electrophilic Addition of Water
  • 10.13 Halogenation—Addition of Halogen
  • 10.14 Stereochemistry of Halogenation
  • 10.15 Halohydrin Formation
  • 10.16 Hydroboration–Oxidation
  • 10.17 Addition of Hydrogen Halides and Halogens to Alkynes
  • 10.18 Addition of Water to Alkynes
  • 10.19 Hydroboration–Oxidation of Alkynes
  • 10.20 Reaction of Acetylide Anions
  • 10.21 Synthesis
  • Chapter Review
  • Problems
• 11 Oxidation and Reduction
  • 11.1 Introduction
  • 11.2 Reducing Agents
  • 11.3 Reduction of Alkenes
  • 11.4 Application: Hydrogenation of Oils
  • 11.5 Reduction of Alkynes
  • 11.6 The Reduction of Polar C–X σ Bonds
  • 11.7 Oxidizing Agents
  • 11.8 Epoxidation
  • 11.9 Dihydroxylation
  • 11.10 Oxidative Cleavage of Alkenes
  • 11.11 Oxidative Cleavage of Alkynes
  • 11.12 Oxidation of Alcohols
  • 11.13 Biological Oxidation
  • 11.14 Sharpless Epoxidation
  • Chapter Review
  • Problems
• 12 Conjugation, Resonance, and Dienes
  • 12.1 Conjugation
  • 12.2 Resonance and Allylic Carbocations
  • 12.3 Common Examples of Resonance
  • 12.4 The Resonance Hybrid
  • 12.5 Electron Delocalization, Hybridization, and Geometry
  • 12.6 Conjugated Dienes
  • 12.7 Interesting Dienes and Polyenes
  • 12.8 The Carbon–Carbon σ Bond Length in Buta-1,3-diene
  • 12.9 Stability of Conjugated Dienes
  • 12.10 Electrophilic Addition: 1,2- Versus 1,4-Addition
  • 12.11 Kinetic Versus Thermodynamic Products
  • 12.12 The Diels–Alder Reaction
  • 12.13 Specific Rules Governing the Diels–Alder Reaction
  • 12.14 Other Facts About the Diels–Alder Reaction
  • Chapter Review
  • Problems
• Spectroscopy A  Mass Spectrometry
  • A.1Mass Spectrometry and the Molecular Ion
  • A.2Alkyl Halides and the M + 2 Peak
  • A.3Fragmentation
  • A.4Fragmentation Patterns of Some Common Functional Groups
  • A.5Other Types of Mass Spectrometry
  • ChapterReview
  • Problems
• Spectroscopy B  Infrared Spectroscopy
  • B.1 Electromagnetic Radiation
  • B.2 The General Features of Infrared Spectroscopy
  • B.3 IR Absorptions
  • B.4 Infrared Spectra of Common Functional Groups
  • B.5 IR and Structure Determination
  • Chapter Review
  • Problems
• Spectroscopy C  Nuclear Magnetic Resonance Spectroscopy
  • C.1An Introduction to NMR Spectroscopy
  • C.21H NMR: Number of Signals
  • C.31H NMR: Position of Signals
  • C.4The Chemical Shift of Protons on sp2and spHybridized Carbons
  • C.51H NMR: Intensity of Signals
  • C.61H NMR: Spin–Spin Splitting
  • C.7More-Complex Examples of Splitting
  • C.8Spin–Spin Splitting in Alkenes
  • C.9Other Facts About 1H NMR Spectroscopy
  • C.10Using 1H NMR to Identify an Unknown
  • C.1113C NMR Spectroscopy
  • C.12Magnetic Resonance Imaging (MRI)
  • Chapter Review
  • Problems
• 13 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction
  • 13.1 Introduction
  • 13.2 General Reactions of Carbonyl Compounds
  • 13.3 A Preview of Oxidation and Reduction
  • 13.4 Reduction of Aldehydes and Ketones
  • 13.5 The Stereochemistry of Carbonyl Reduction
  • 13.6 Enantioselective Biological Reduction
  • 13.7 Reduction of Carboxylic Acids and Their Derivatives
  • 13.8 Oxidation of Aldehydes
  • 13.9 Organometallic Reagents
  • 13.10 Reaction of Organometallic Reagents with Aldehydes and Ketones
  • 13.11 Retrosynthetic Analysis of Grignard Products
  • 13.12 Protecting Groups
  • 13.13 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives
  • 13.14 Reaction of Organometallic Reagents with Other Compounds
  • 13.15 α,β-Unsaturated Carbonyl Compounds
  • 13.16 Summary—The Reactions of Organometallic Reagents
  • 13.17 Synthesis
  • ChapterReview
  • Problems
• 14 Aldehydes and Ketones—Nucleophilic Addition
  • 14.1 Introduction
  • 14.2 Nomenclature
  • 14.3 Properties of Aldehydes and Ketones
  • 14.4 Interesting Aldehydes and Ketones
  • 14.5 Preparation of Aldehydes and Ketones
  • 14.6 Reactions of Aldehydes and Ketones—General Considerations
  • 14.7 Nucleophilic Addition of H−and R−—A Review
  • 14.8 Nucleophilic Addition of −CN
  • 14.9 The Wittig Reaction
  • 14.10 Addition of 1° Amines
  • 14.11 Addition of 2° Amines
  • 14.12 Imine and Enamine Hydrolysis
  • 14.13 Imines in Biological Systems
  • 14.14 Addition of H2O—Hydration
  • 14.15 Addition of Alcohols—Acetal Formation
  • 14.16 Acetals as Protecting Groups
  • 14.17 Cyclic Hemiacetals
  • 14.18 An Introduction to Carbohydrates
  • ChapterReview
  • Problems
• 15 Carboxylic Acids and Nitriles
  • 15.1 Structure and Bonding
  • 15.2 Nomenclature
  • 15.3 Physical and Spectroscopic Properties
  • 15.4 Interesting Carboxylic Acids and Nitriles
  • 15.5 Aspirin, Arachidonic Acid, and Prostaglandins
  • 15.6 Preparation of Carboxylic Acids
  • 15.7 Carboxylic Acids—Strong Organic Brønsted–Lowry Acids
  • 15.8 The Henderson–Hasselbalch Equation
  • 15.9 Inductive Effects in Aliphatic Carboxylic Acids
  • 15.10 Extraction
  • 15.11 Organic Acids That Contain Phosphorus
  • 15.12 Amino Acids
  • 15.13 Nitriles
  • ChapterReview
  • Problems
• 16 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution
  • 16.1 Introduction
  • 16.2 Structure and Bonding
  • 16.3 Nomenclature
  • 16.4 Physical and Spectroscopic Properties
  • 16.5 Interesting Esters and Amides
  • 16.6 Introduction to Nucleophilic Acyl Substitution
  • 16.7 Reactions of Acid Chlorides
  • 16.8 Reactions of Anhydrides
  • 16.9 Reactions of Carboxylic Acids
  • 16.10 Reactions of Esters
  • 16.11 Application: Lipid Hydrolysis
  • 16.12 Reactions of Amides
  • 16.13 Application: The Mechanism of Action of β-Lactam Antibiotics
  • 16.14 Summary of Nucleophilic Acyl Substitution Reactions
  • 16.15 Acyl Phosphates—Biological Anhydrides
  • 16.16 Reactions of Thioesters—Biological Acylation Reactions
  • ChapterReview
  • Problems
• 17 Substitution Reactions of Carbonyl Compounds at the α Carbon
  • 17.1 Introduction
  • 17.2 Enols
  • 17.3 Enolates
  • 17.4 Enolates of Unsymmetrical Carbonyl Compounds
  • 17.5 Racemization at the α Carbon
  • 17.6 A Preview of Reactions at the α Carbon
  • 17.7 Halogenation at the α Carbon
  • 17.8 Direct Enolate Alkylation
  • 17.9 Malonic Ester Synthesis
  • 17.10 Acetoacetic Ester Synthesis
  • 17.11 Biological Decarboxylation
  • ChapterReview
  • Problems
• 18 Carbonyl Condensation Reactions
  • 18.1 The Aldol Reaction
  • 18.2 Crossed Aldol Reactions
  • 18.3 Directed Aldol Reactions
  • 18.4 Intramolecular Aldol Reactions
  • 18.5 The Claisen Reaction
  • 18.6 The Crossed Claisen and Related Reactions
  • 18.7 The Dieckmann Reaction
  • 18.8 Biological Carbonyl Condensation Reactions
  • 18.9 The Michael Reaction
  • 18.10 The Robinson Annulation
  • ChapterReview
  • Problems
• 19 Benzene and Aromatic Compounds
  • 19.1 Background
  • 19.2 The Structure of Benzene
  • 19.3 Nomenclature of Benzene Derivatives
  • 19.4 Spectroscopic Properties
  • 19.5 Interesting Aromatic Compounds
  • 19.6 Benzene’s Unusual Stability
  • 19.7 The Criteria for Aromaticity—Hückel’s Rule
  • 19.8 Examples of Aromatic Compounds
  • 19.9 Aromatic Heterocycles
  • 19.10 What Is the Basis of Hückel’s Rule?
  • 19.11 The Inscribed Polygon Method for Predicting Aromaticity
  • 19.12 Aromatase Inhibitors for Estrogen-Dependent Cancer Treatment
  • ChapterReview
  • Problems
• 20 Reactions of Aromatic Compounds
  • 20.1 Electrophilic Aromatic Substitution
  • 20.2 The General Mechanism
  • 20.3 Halogenation
  • 20.4 Nitration and Sulfonation
  • 20.5 Friedel–Crafts Alkylation and Friedel–Crafts Acylation
  • 20.6 Substituted Benzenes
  • 20.7 Electrophilic Aromatic Substitution of Substituted Benzenes
  • 20.8 Why Substituents Activate or Deactivate a Benzene Ring
  • 20.9 Orientation Effects in Substituted Benzenes
  • 20.10 Limitations on Electrophilic Substitution Reactions with Substituted Benzenes
  • 20.11 Disubstituted Benzenes
  • 20.12 Synthesis of Benzene Derivatives
  • 20.13 Nucleophilic Aromatic Substitution
  • 20.14 Reactions of Substituted Benzenes
  • 20.15 Multistep Synthesis
  • ChapterReview
  • Problems
• 21 Radical Reactions
  • 21.1 Introduction
  • 21.2 General Features of Radical Reactions
  • 21.3 Halogenation of Alkanes
  • 21.4 The Mechanism of Halogenation
  • 21.5 Chlorination of Other Alkanes
  • 21.6 Chlorination Versus Bromination
  • 21.7 The Stereochemistry of Halogenation Reactions
  • 21.8 Application: The Ozone Layer and CFCs
  • 21.9 Radical Halogenation at an Allylic Carbon
  • 21.10 Application: Oxidation of Unsaturated Lipids
  • 21.11 Application: Antioxidants
  • 21.12 Radical Addition Reactions to Double Bonds
  • 21.13 Polymers and Polymerization
  • Chapter Review
  • Problems
• 22 Amines
  • 22.1 Introduction
  • 22.2 Structure and Bonding
  • 22.3 Nomenclature
  • 22.4 Physical and Spectroscopic Properties
  • 22.5 Interesting and Useful Amines
  • 22.6 Preparation of Amines
  • 22.7 Reactions of Amines—General Features
  • 22.8 Amines as Bases
  • 22.9 Relative Basicity of Amines and Other Compounds
  • 22.10 Amines as Nucleophiles
  • 22.11 Hofmann Elimination
  • 22.12 Reaction of Amines with Nitrous Acid
  • 22.13 Substitution Reactions of Aryl Diazonium Salts
  • 22.14 Coupling Reactions of Aryl Diazonium Salts
  • 22.15 Application: Synthetic Dyes and Sulfa Drugs
  • ChapterReview
  • Problems
• 23 Amino Acids and Proteins
  • 23.1 Amino Acids
  • 23.2 Separation of Amino Acids
  • 23.3 Enantioselective Synthesis of Amino Acids
  • 23.4 Peptides
  • 23.5 Peptide Sequencing
  • 23.6 Peptide Synthesis
  • 23.7 Automated Peptide Synthesis
  • 23.8 Protein Structure
  • 23.9 Important Proteins
  • 23.10 Enzymes
  • ChapterReview
  • Problems
• 24 Carbohydrates
  • 24.1 Introduction
  • 24.2 Monosaccharides
  • 24.3 The Family of D-Aldoses
  • 24.4 The Family of D-Ketoses
  • 24.5 Physical Properties of Monosaccharides
  • 24.6 The Cyclic Forms of Monosaccharides
  • 24.7 Glycosides
  • 24.8 Reactions of Monosaccharides at the OH Groups
  • 24.9 Reactions at the Carbonyl Group—Oxidation and Reduction
  • 24.10 Reactions at the Carbonyl Group—Adding or Removing One Carbon Atom
  • 24.11 Disaccharides
  • 24.12 Polysaccharides
  • 24.13 Other Important Sugars and Their Derivatives
  • ChapterReview
  • Problems
• 25 Lipids
  • 25.1 Introduction
  • 25.2 Waxes
  • 25.3 Triacylglycerols
  • 25.4 Phospholipids
  • 25.5 Fat-Soluble Vitamins
  • 25.6 Eicosanoids
  • 25.7 Terpenes
  • 25.8 Steroids
  • ChapterReview
  • Problems
• 26 Nucleic Acids and Protein Synthesis
  • 26.1 Nucleosides and Nucleotides
  • 26.2 Nucleic Acids
  • 26.3 The DNA Double Helix
  • 26.4 Replication
  • 26.5 Ribonucleic Acids and Transcription
  • 26.6 The Genetic Code, Translation, and Protein Synthesis
  • 26.7 DNA Sequencing
  • 26.8 The Polymerase Chain Reaction
  • 26.9 Viruses
  • ChapterReview
  • Problems
• 27 Metabolism
  • 27.1 Overview of Metabolism
  • 27.2Key Oxidizing and Reducing Agents in Metabolism
  • 27.3 The Catabolism of Triacylglycerols by β-Oxidation
  • 27.4 The Catabolism of Carbohydrates—Glycolysis
  • 27.5 The Fate of Pyruvate
  • 27.6 The Citric Acid Cycle and ATP Production
  • ChapterReview
  • Problems
• 28 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis (Available Online)
  • 28.1 Coupling Reactions of Organocuprate Reagents
  • 28.2 Suzuki Reaction
  • 28.3 Heck Reaction
  • 28.4 Carbenes and Cyclopropane Synthesis
  • 28.5 Simmons–Smith Reaction
  • 28.6 Metathesis
  • ChapterReview
  • Problems
• 29 Pericyclic Reactions (Available Online)
  • 29.1 Types of Pericyclic Reactions
  • 29.2 Molecular Orbitals
  • 29.3 Electrocyclic Reactions
  • 29.4 Cycloaddition Reactions
  • 29.5 Sigmatropic Rearrangements
  • 29.6 Summary of Rules for Pericyclic Reactions
  • ChapterReview
  • Problems
• 30 Synthetic Polymers (Available Online)
  • 30.1 Introduction
  • 30.2 Chain-Growth Polymers—Addition Polymers
  • 30.3 Anionic Polymerization of Epoxides
  • 30.4 Ziegler–Natta Catalysts and Polymer Stereochemistry
  • 30.5 Natural and Synthetic Rubbers
  • 30.6 Step-Growth Polymers—Condensation Polymers
  • 30.7 Polymer Structure and Properties
  • 30.8 Green Polymer Synthesis
  • 30.9 Polymer Recycling and Disposal
  • ChapterReview
  • Problems
• Appendix A Periodic Table of the Elements A-
• Appendix BCommon Abbreviations, Arrows, and Symbols A-
• Appendix CpKaValues for Selected Compounds A-
• Appendix DNomenclature A-
• Appendix E Bond Dissociation Energies for Some Common Bonds [A–B → A• + •B] A-
• Appendix F Reactions That Form Carbon–Carbon Bonds A-
• Appendix G Characteristic IR Absorption Frequencies A-
• Appendix H Characteristic NMR Absorptions A-
• Appendix I General Types of Organic Reactions A-
• Appendix J How to Synthesize Particular Functional Groups A-
• Glossary
• Index

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