Organic Chemistry

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Half-Title Page Title Page Copyright Page Brief Contents Contents Preface Changes and Additions for This Eighth Edition Features A Complete Ancillary Package Acknowledgments Chapter 1: Structure and Bonding 1.1: Atomic Structure: The Nucleus 1.2: Atomic Structure: Orbitals 1.3: Atomic Structure: Electron Configurations 1.4: Development of Chemical Bonding Theory 1.5: Describing Chemical Bonds: Valence Bond Theory 1.6: sp3 Hybrid Orbitals and the Structure of Methane 1.7: sp3 Hybrid Orbitals and the Structure of Ethane 1.8: sp2 Hybrid Orbitals and the Structure of Ethylene 1.9: sp Hybrid Orbitals and the Structure of Acetylene 1.10: Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur 1.11: Describing Chemical Bonds: Molecular Orbital Theory 1.12: Drawing Chemical Structures A Deeper Look: Organic Foods: Risk versus Benefit Summary Key words Working Problems Exercises Chapter 2: Polar Covalent Bonds; Acids and Bases 2.1: Polar Covalent Bonds: Electronegativity 2.2: Polar Covalent Bonds: Dipole Moments 2.3: Formal Charges 2.4: Resonance 2.5: Rules for Resonance Forms 2.6: Drawing Resonance Forms 2.7: Acids and Bases: The Brønsted–Lowry Definition 2.8: Acid and Base Strength 2.9: Predicting Acid–Base Reactions from pKa Values 2.10: Organic Acids and Organic Bases 2.11: Acids and Bases: The Lewis Definition 2.12: Noncovalent Interactions Between Molecules A Deeper Look: Alkaloids: From Cocaine to Dental Anesthetics Summary Key words Exercises Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry 3.1: Functional Groups 3.2: Alkanes and Alkane Isomers 3.3: Alkyl Groups 3.4: Naming Alkanes 3.5: Properties of Alkanes 3.6: Conformations of Ethane 3.7: Conformations of Other Alkanes A Deeper Look: Gasoline Summary Key words Exercises Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry 4.1: Naming Cycloalkanes 4.2: Cis–Trans Isomerism in Cycloalkanes 4.3: Stability of Cycloalkanes: Ring Strain 4.4: Conformations of Cycloalkanes 4.5: Conformations of Cyclohexane 4.6: Axial and Equatorial Bonds in Cyclohexane 4.7: Conformations of Monosubstituted Cyclohexanes 4.8: Conformations of Disubstituted Cyclohexanes 4.9: Conformations of Polycyclic Molecules A Deeper Look: Molecular Mechanics Summary Key words Exercises Chapter 5: Stereochemistry at Tetrahedral Centers 5.1: Enantiomers and the Tetrahedral Carbon 5.2: The Reason for Handedness in Molecules: Chirality 5.3: Optical Activity 5.4: Pasteur’s Discovery of Enantiomers 5.5: Sequence Rules for Specifying Configuration 5.6: Diastereomers 5.7: Meso Compounds 5.8: Racemic Mixtures and the Resolution of Enantiomers 5.9: A Review of Isomerism 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur 5.11: Prochirality 5.12: Chirality in Nature and Chiral Environments A Deeper Look: Chiral Drugs Summary Key words Exercises Chapter 6: An Overview of Organic Reactions 6.1: Kinds of Organic Reactions 6.2: How Organic Reactions Occur: Mechanisms 6.3: Radical Reactions 6.4: Polar Reactions 6.5: An Example of a Polar Reaction: Addition of HBr to Ethylene 6.6: Using Curved Arrows in Polar Reaction Mechanisms 6.7: Describing a Reaction: Equilibria, Rates, and Energy Changes 6.8: Describing a Reaction: Bond Dissociation Energies 6.9: Describing a Reaction: Energy Diagrams and Transition States 6.10: Describing a Reaction: Intermediates 6.11: A Comparison Between Biological Reactions and Laboratory Reactions A Deeper Look: Where Do Drugs Come From? Summary Key words Exercises Chapter 7: Alkenes: Structure and Reactivity 7.1: Industrial Preparation and Use of Alkenes 7.2: Calculating Degree of Unsaturation 7.3: Naming Alkenes 7.4: Cis–Trans Isomerism in Alkenes 7.5: Alkene Stereochemistry and the E,Z Designation 7.6: Stability of Alkenes 7.7: Electrophilic Addition Reactions of Alkenes 7.8: Orientation of Electrophilic Additions: Markovnikov’s Rule 7.9: Carbocation Structure and Stability 7.10: The Hammond Postulate 7.11: Evidence for the Mechanism of Electrophilic Additions:Carbocation Rearrangements A Deeper Look: Bioprospecting: Hunting for Natural Products Summary Key words Exercises Chapter 8: Alkenes: Reactions and Synthesis 8.1: Preparing Alkenes: A Preview of Elimination Reactions 8.2: Halogenation of Alkenes: Addition of X2 8.3: Halohydrins from Alkenes: Addition of HOX 8.4: Hydration of Alkenes: Additionof H2O by Oxymercuration 8.5: Hydration of Alkenes: Addition of H2O by Hydroboration 8.6: Reduction of Alkenes: Hydrogenation 8.7: Oxidation of Alkenes: Epoxidation and Hydroxylation 8.8: Oxidation of Alkenes: Cleavage to Carbonyl Compounds 8.9: Addition of Carbenes to Alkenes: Cyclopropane Synthesis 8.10: Radical Additions to Alkenes: Chain-Growth Polymers 8.11: Biological Additions of Radicals to Alkenes 8.12: Reaction Stereochemistry: Addition of H2O to an Achiral Alkene 8.13: Reaction Stereochemistry: Addition of H2O to a Chiral Alkene A Deeper Look: Terpenes: Naturally Occurring Alkenes Summary Key words Learning Reactions Summary of Reactions Exercises Chapter 9: Alkynes: An Introduction to Organic Synthesis 9.1: Naming Alkynes 9.2: Preparation of Alkynes: Elimination Reactions of Dihalides 9.3: Reactions of Alkynes: Addition of HX and X2 9.4: Hydration of Alkynes 9.5: Reduction of Alkynes 9.6: Oxidative Cleavage of Alkynes 9.7: Alkyne Acidity: Formation of Acetylide Anions 9.8: Alkylation of Acetylide Anions 9.9: An Introduction to Organic Synthesis A Deeper Look: The Art of Organic Synthesis Summary Key words Summary of Reactions Exercises Chapter 10: Organohalides 10.1: Names and Properties of Alkyl Halides 10.2: Preparing Alkyl Halides from Alkanes: Radical Halogenation 10.3: Preparing Alkyl Halides from Alkenes: Allylic Bromination 10.4: Stability of the Allyl Radical: Resonance Revisited 10.5: Preparing Alkyl Halides from Alcohols 10.6: Reactions of Alkyl Halides: Grignard Reagents 10.7: Organometallic Coupling Reactions 10.8: Oxidation and Reduction in Organic Chemistry A Deeper Look: Naturally Occurring Organohalides Summary Key words Summary of Reactions Exercises Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 11.1: The Discovery of Nucleophilic Substitution Reactions 11.2: The SN2 Reaction 11.3: Characteristics of the SN2 Reaction 11.4: The SN1 Reaction 11.5: Characteristics of the SN1 Reaction 11.6: Biological Substitution Reactions 11.7: Elimination Reactions: Zaitsev’s Rule 11.8: The E2 Reaction and the Deuterium Isotope Effect 11.9: The E2 Reaction and Cyclohexane Conformation 11.10: The E1 and E1cB Reactions 11.11: Biological Elimination Reactions 11.12: A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2 A Deeper Look: Green Chemistry Summary Key words Summary of Reactions Exercises Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy 12.1: Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments 12.2: Interpreting Mass Spectra 12.3: Mass Spectrometry of Some Common Functional Groups 12.4: Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments 12.5: Spectroscopy and the Electromagnetic Spectrum 12.6: Infrared Spectroscopy 12.7: Interpreting Infrared Spectra 12.8: Infrared Spectra of Some Common Functional Groups A Deeper Look: X-Ray Crystallography Summary Key words Exercises Chapter 13: Structure Determination :Nuclear Magnetic Resonance Spectroscopy 13.1: Nuclear Magnetic Resonance Spectroscopy 13.2: The Nature of NMR Absorptions 13.3: Chemical Shifts 13.4: 13C NMR Spectroscopy: Signal Averaging and FT–NMR 13.5: Characteristics of 13C NMR Spectroscopy 13.6: DEPT 13C NMR Spectroscopy 13.7: Uses of 13C NMR Spectroscopy 13.8: 1H NMR Spectroscopy and Proton Equivalence 13.9: Chemical Shifts in 1H NMR Spectroscopy 13.10: Integration of 1H NMR Absorptions: Proton Counting 13.11: Spin–Spin Splitting in 1H NMR Spectra 13.12: More Complex Spin–Spin Splitting Patterns 13.13: Uses of 1H NMR Spectroscopy A Deeper Look: Magnetic Resonance Imaging (MRI) Summary Key words Exercises Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy 14.1: Stability of Conjugated Dienes: Molecular Orbital Theory 14.2: Electrophilic Additions to Conjugated Dienes: Allylic Carbocations 14.3: Kinetic versus Thermodynamic Control of Reactions 14.4: The Diels–Alder Cycloaddition Reaction 14.5: Characteristics of the Diels–Alder Reaction 14.6: Diene Polymers: Natural and Synthetic Rubbers 14.7: Structure Determination in Conjugated Systems: Ultraviolet Spectroscopy 14.8: Interpreting Ultraviolet Spectra: The Effect of Conjugation 14.9: Conjugation, Color, and the Chemistry of Vision A Deeper Look: Photolithography Summary Key words Summary of Reactions Exercises Chapter 15: Benzene and Aromaticity 15.1: Sources and Names of Aromatic Compounds 15.2: Structure and Stability of Benzene 15.3: Aromaticity and the Hückel 4n + 2 Rule 15.4: Aromatic Ions 15.5: Aromatic Heterocycles: Pyridine and Pyrrole 15.6: Polycyclic Aromatic Compounds 15.7: Spectroscopy of Aromatic Compounds A Deeper Look: Aspirin, NSAIDs, and COX-2 Inhibitors Summary Key words Exercises Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution 16.1: Electrophilic Aromatic Substitution Reactions: Bromination 16.2: Other Aromatic Substitutions 16.3: Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction 16.4: Substituent Effects in Substituted Aromatic Rings 16.5: An Explanation of Substituent Effects 16.6: Trisubstituted Benzenes: Additivity of Effects 16.7: Nucleophilic Aromatic Substitution 16.8: Benzyne 16.9: Oxidation of Aromatic Compounds 16.10: Reduction of Aromatic Compounds 16.11: Synthesis of Polysubstituted Benzenes A Deeper Look: Combinatorial Chemistry Summary Key words Summary of Reactions Exercises Chapter 17:Alcohols and Phenols 17.1: Naming Alcohols and Phenols 17.2: Properties of Alcohols and Phenols 17.3: Preparation of Alcohols: A Review 17.4: Alcohols from Carbonyl Compounds Reduction 17.5: Alcohols from Carbonyl Compounds: Grignard Reaction 17.6: Reactions of Alcohols 17.7: Oxidation of Alcohols 17.8: Protection of Alcohols 17.9: Phenols and Their Uses 17.10: Reactions of Phenols 17.11: Spectroscopy of Alcohols and Phenols A Deeper Look: Ethanol: Chemical, Drug, Poison Summary Key words Summary of Reactions Exercises Chapter 18: Ethers and Epoxides; Thiols and Sulfides 18.1: Names and Properties of Ethers 18.2: Synthesis of Ethers 18.3: Reactions of Ethers: Acidic Cleavage 18.4: Reactions of Ethers: Claisen Rearrangement 18.5: Cyclic Ethers: Epoxides 18.6: Reactions of Epoxides: Ring-Opening 18.7: Crown Ethers 18.8: Thiols and Sulfides 18.9: Spectroscopy of Ethers A Deeper Look: Epoxy Resins and Adhesives Summary Key words Summary of Reactions Exercises Preview of Carbonyl Chemistry I: Kinds of Carbonyl Compounds Il: Nature of the Carbonyl Group III: General Reactions of Carbonyl Compounds IV: Summary Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions 19.1: Naming Aldehydes and Ketones 19.2: Preparing Aldehydes and Ketones 19.3: Oxidation of Aldehydes and Ketones 19.4: Nucleophilic Addition Reactions of Aldehydes and Ketones 19.5: Nucleophilic Addition of H2O: Hydration 19.6: Nucleophilic Addition of HCN:Cyanohydrin Formation 19.7: Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation 19.8: Nucleophilic Addition of Amines: Imine and Enamine Formation 19.9: Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction 19.10: Nucleophilic Addition of Alcohols: Acetal Formation 19.11: Nucleophilic Addition of PhosphorusYlides: The Wittig Reaction 19.12: Biological Reductions 19.13: Conjugate Nucleophilic Addition toa, b-Unsaturated Aldehydes and Ketones 19.14: Spectroscopy of Aldehydes and Ketones A Deeper Look: Enantioselective Synthesis Summary Key words Summary of Reactions Exercises Chapter 20: Carboxylic Acids and Nitriles 20.1: Naming Carboxylic Acids and Nitriles 20.2: Structure and Properties of Carboxylic Acids 20.3: Biological Acids and the Henderson–Hasselbalch Equation 20.4: Substituent Effects on Acidity 20.5: Preparing Carboxylic Acids 20.6: Reactions of Carboxylic Acids: An Overview 20.7: Chemistry of Nitriles 20.8: Spectroscopy of Carboxylic Acids and Nitriles A Deeper Look: Vitamin C Summary Key words Summary of Reactions Exercises Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 21.1: Naming Carboxylic Acid Derivatives 21.2: Nucleophilic Acyl Substitution Reactions 21.3: Nucleophilic Acyl Substitution Reactions of Carboxylic Acids 21.4: Chemistry of Acid Halides 21.5: Chemistry of Acid Anhydrides 21.6: Chemistry of Esters 21.7: Chemistry of Amides 21.8: Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives 21.9: Polyamides and Polyesters: Step-Growth Polymers 21.10: Spectroscopy of Carboxylic Acid Derivatives A Deeper Look: b-Lactam Antibiotics Summary Key words Summary of Reactions Exercises Chapter 22: Carbonyl Alpha-Substitution Reactions 22.1: Keto–Enol Tautomerism 22.2: Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions 22.3: Alpha Halogenation of Aldehydes and Ketones 22.4: Alpha Bromination of Carboxylic Acids 22.5: Acidity of Alpha Hydrogen Atoms:Enolate Ion Formation 22.6: Reactivity of Enolate Ions 22.7: Alkylation of Enolate Ions A Deeper Look: Barbiturates Summary Key words Summary of Reactions Exercises Chapter 23: Carbonyl Condensation Reactions 23.1: Carbonyl Condensations: The Aldol Reaction 23.2: Carbonyl Condensations versus Alpha Substitutions 23.3: Dehydration of Aldol Products: Synthesis of Enones 23.4: Using Aldol Reactions in Synthesis 23.5: Mixed Aldol Reactions 23.6: Intramolecular Aldol Reactions 23.7: The Claisen Condensation Reaction 23.8: Mixed Claisen Condensations 23.9: Intramolecular Claisen Condensations: The Dieckmann Cyclization 23.10: Conjugate Carbonyl Additions: The Michael Reaction 23.11: Carbonyl Condensations with Enamines: The Stork Reaction 23.12: The Robinson Annulation Reaction 23.13: Some Biological Carbonyl Condensation Reactions A Deeper Look: A Prologue to Metabolism Summary Key words Summary of Reactions Exercises Chapter 24: Amines and Heterocycles 24.1: Naming Amines 24.2: Structure and Properties of Amines 24.3: Basicity of Amines 24.4: Basicity of Arylamines 24.5: Biological Amines and the Henderson–Hasselbalch Equation 24.6: Synthesis of Amines 24.7: Reactions of Amines 24.8: Reactions of Arylamines 24.9: Heterocyclic Amines 24.10: Spectroscopy of Amines A Deeper Look: Green Chemistry II: Ionic Liquids Summary Key words Summary of Reactions Exercises Chapter 25: Biomolecules: Carbohydrates 25.1: Classification of Carbohydrates 25.2: Depicting Carbohydrate Stereochemistry: Fischer Projections 25.3: D,L Sugars 25.4: Configurations of Aldoses 25.5: Cyclic Structures of Monosaccharides: Anomers 25.6: Reactions of Monosaccharides 25.7: The Eight Essential Monosaccharides 25.8: Disaccharides 25.9: Polysaccharides and Their Synthesis 25.10: Other Important Carbohydrates 25.11: Cell-Surface Carbohydrates and Influenza Viruses A Deeper Look: Sweetness Summary Key words Summary of Reactions Exercises Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins 26.1: Structures of Amino Acids 26.2: Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points 26.3: Synthesis of Amino Acids 26.4: Peptides and Proteins 26.5: Amino Acid Analysis of Peptides 26.6: Peptide Sequencing:The Edman Degradation 26.7: Peptide Synthesis 26.8: Automated Peptide Synthesis: The Merrifield Solid-Phase Method 26.9: Protein Structure 26.10: Enzymes and Coenzymes 26.11: How Do Enzymes Work? Citrate Synthase A Deeper Look: The Protein Data Bank Summary Key words Summary of Reactions Exercises Chapter 27: Biomolecules: Lipids 27.1: Waxes, Fats, and Oils 27.2: Soap 27.3: Phospholipids 27.4: Prostaglandins and Other Eicosanoids 27.5: Terpenoids 27.6: Steroids 27.7: Biosynthesis of Steroids A Deeper Look: Saturated Fats, Cholesterol, and Heart Disease Summary Key words Exercises Chapter 28: Biomolecules: Nucleic Acids 28.1: Nucleotides and Nucleic Acids 28.2: Base Pairing in DNA: The Watson–Crick Model 28.3: Replication of DNA 28.4: Transcription of DNA 28.5: Translation of RNA: Protein Biosynthesis 28.6: DNA Sequencing 28.7: DNA Synthesis 28.8: The Polymerase Chain Reaction A Deeper Look: DNA Fingerprinting Summary Key words Exercises Chapter 29: The Organic Chemistry of Metabolic Pathways 29.1: An Overview of Metabolism and Biochemical Energy 29.2: Catabolism of Triacylglycerols: The Fate of Glycerol 29.3: Catabolism of Triacylglycerols: b-Oxidation 29.4: Biosynthesis of Fatty Acids 29.5: Catabolism of Carbohydrates: Glycolysis 29.6: Conversion of Pyruvate to Acetyl CoA 29.7: The Citric Acid Cycle 29.8: Carbohydrate Biosynthesis: Gluconeogenesis 29.9: Catabolism of Proteins: Deamination 29.10: Some Conclusions about Biological Chemistry A Deeper Look: Statin Drugs Summary Key words Exercises Chapter 30: Orbitals and Organic Chemistry: Pericyclic Reactions 30.1: Molecular Orbitals of Conjugated Pi Systems 30.2: Electrocyclic Reactions 30.3: Stereochemistry of Thermal Electrocyclic Reactions 30.4: Photochemical Electrocyclic Reactions 30.5: Cycloaddition Reactions 30.6: Stereochemistry of Cycloadditions 30.7: Sigmatropic Rearrangements 30.8: Some Examples of Sigmatropic Rearrangements 30.9: A Summary of Rules for Pericyclic Reactions A Deeper Look: Vitamin D, the Sunshine Vitamin Summary Key words Exercises Chapter 31: Synthetic Polymers 31.1: Chain-Growth Polymers 31.2: Stereochemistry of Polymerization: Ziegler–Natta Catalysts 31.3: Copolymers 31.4: Step-Growth Polymers 31.5: Olefin Metathesis Polymerization 31.6: Polymer Structure and Physical Properties A Deeper Look: Biodegradable Polymers Summary Key words Exercises Appendix A: Nomenclature of Polyfunctional Organic Compounds Name Part 1. The Suffix: Functional-Group Precedence Name Part 2. The Parent: Selecting the Main Chain or Ring Name Parts 3 and 4. The Prefixes and Locants Writing the Name Additional Reading Appendix B: Acidity Constants for Some Organic Compounds Appendix C: Glossary Glossary Appendix D: Answers to In-Text Problems Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Preview of Carbonyl Chemistry Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26 Chapter 27 Chapter 28 Chapter 29 Chapter 30 Chapter 31 Index Untitled