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• Cover
• Title Page
• Copyright Page
• Dedication
• Preface
• 1 A Review of General Chemistry
• 1.1 Introduction to Organic Chemistry
• 1.2 The Structural Theory of Matter
• 1.3 Electrons, Bonds, and Lewis Structures
• 1.4 Identifying Formal Charges
• 1.5 Induction and Polar Covalent Bonds
• 1.6 Reading Bond-Line Structures
• 1.7 Atomic Orbitals
• 1.8 Valence Bond Theory
• 1.9 Molecular Orbital Theory
• 1.10 Hybridized Atomic Orbitals
• 1.11 Predicting Molecular Geometry: VSEPR Theory
• 1.12 Dipole Moments and Molecular Polarity
• 1.13 Intermolecular Forces and Physical Properties
• 1.14 Solubility
• REVIEW OF CONCEPTS AND VOCABULARY
• SKILLBUILDER REVIEW
• PRACTICE PROBLEMS
• ACS-STYLE PROBLEMS (Multiple Choice)
• INTEGRATED PROBLEMS
• CHALLENGE PROBLEMS
• 2 Molecular Representations
• 2.1 Molecular Representations
• 2.2 Drawing Bond-Line Structures
• 2.3 Identifying Functional Groups
• 2.4 Carbon Atoms with Formal Charges
• 2.5 Identifying Lone Pairs
• 2.6 Three-Dimensional Bond-Line Structures
• 2.7 Introduction to Resonance
• 2.8 Curved Arrows
• 2.9 Formal Charges in Resonance Structures
• 2.10 Drawing Resonance Structures via Pattern Recognition
• 2.11 Assessing the Relative Importance of Resonance Structures
• 2.12 The Resonance Hybrid
• 2.13 Delocalized and Localized Lone Pairs
• REVIEW OF CONCEPTS AND VOCABULARY
• SKILLBUILDER REVIEW
• PRACTICE PROBLEMS
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• 3 Acids and Bases
• 3.1 Introduction to Brønsted-Lowry Acids and Bases
• 3.2 Flow of Electron Density: Curved-Arrow Notation
• 3.3 Brønsted-Lowry Acidity: Comparing pKa Values
• 3.4 Brønsted-Lowry Acidity: Factors Affecting the Stability of Anions
• 3.5 Bronsted-Lowry Acidity: Assessing the Relative Acidity of Cationic Acids
• 3.6 Position of Equilibrium and Choice of Reagents
• 3.7 Leveling Effect
• 3.8 Solvating Effects
• 3.9 Counterions
• 3.10 Lewis Acids and Bases
• REVIEW OF CONCEPTS AND VOCABULARY
• SKILLBUILDER REVIEW
• PRACTICE PROBLEMS
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• 4 Alkanes and Cycloalkanes
• 4.1 Introduction to Alkanes
• 4.2 Nomenclature of Alkanes
• 4.3 Constitutional Isomers of Alkanes
• 4.4 Relative Stability of Isomeric Alkanes
• 4.5 Sources and Uses of Alkanes
• 4.6 Drawing Newman Projections
• 4.7 Conformational Analysis of Ethane and Propane
• 4.8 Conformational Analysis of Butane
• 4.9 Cycloalkanes
• 4.10 Conformations of Cyclohexane
• 4.11 Drawing Chair Conformations
• 4.12 Monosubstituted Cyclohexane
• 4.13 Disubstituted Cyclohexane
• 4.14 cis-trans Stereoisomerism
• 4.15 Polycyclic Systems
• REVIEW OF CONCEPTS AND VOCABULARY
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• 5 Stereoisomerism
• 5.1 Overview of Isomerism
• 5.2 Introduction to Stereoisomerism
• 5.3 Designating Configuration Using the Cahn-Ingold-Prelog System
• 5.4 Optical Activity
• 5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers
• 5.6 Symmetry and Chirality
• 5.7 Fischer Projections
• 5.8 Conformationally Mobile Systems
• 5.9 Chiral Compounds that Lack a Chiral Center
• 5.10 Resolution of Enantiomers
• 5.11 E and Z Designations for Diastereomeric Alkenes
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 6 Chemical Reactivity and Mechanisms
• 6.1 Enthalpy
• 6.2 Entropy
• 6.3 Gibbs Free Energy
• 6.4 Equilibria
• 6.5 Kinetics
• 6.6 Reading Energy Diagrams
• 6.7 Nucleophiles and Electrophiles
• 6.8 Mechanisms and Arrow Pushing
• 6.9 Combining the Patterns of Arrow Pushing
• 6.10 Drawing Curved Arrows
• 6.11 Carbocation Rearrangements
• 6.12 Reversible and Irreversible Reaction Arrows
• REVIEW OF CONCEPTS AND VOCABULARY
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• 7 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions
• 7.1 Introduction to Substitution and Elimination Reactions
• 7.2 Nomenclature and Uses of Alkyl Halides
• 7.3 SN2 Reactions
• 7.4 Nucleophilic Strength in SN2 Reactions
• 7.5 Introduction to E2 Reactions
• 7.6 Stability of Alkenes and Cycloalkenes
• 7.7 Regiochemical and Stereochemical Outcomes for E2 Reactions
• 7.8 Unimolecular Reactions (SN1 and E1)
• 7.9 Predicting Products: Substitution vs. Elimination
• 7.10 Substitution and Elimination Reactions with Other Substrates
• 7.11 Synthesis Strategies
• 7.12 Solvent Effects in Substitution Reactions
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 8 Addition Reactions of Alkenes
• 8.1 Introduction to Addition Reactions
• 8.2 Alkenes in Nature and in Industry
• 8.3 Nomenclature of Alkenes
• 8.4 Addition vs. Elimination: A Thermodynamic Perspective
• 8.5 Hydrohalogenation
• 8.6 Acid-Catalyzed Hydration
• 8.7 Oxymercuration-Demercuration
• 8.8 Hydroboration-Oxidation
• 8.9 Catalytic Hydrogenation
• 8.10 Halogenation and Halohydrin Formation
• 8.11 Anti Dihydroxylation
• 8.12 Syn Dihydroxylation
• 8.13 Oxidative Cleavage
• 8.14 Predicting the Products of an Addition Reaction
• 8.15 Synthesis Strategies
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 9 Alkynes
• 9.1 Introduction to Alkynes
• 9.2 Nomenclature of Alkynes
• 9.3 Acidity of Acetylene and Terminal Alkynes
• 9.4 Preparation of Alkynes
• 9.5 Reduction of Alkynes
• 9.6 Hydrohalogenation of Alkynes
• 9.7 Hydration of Alkynes
• 9.8 Halogenation of Alkynes
• 9.9 Ozonolysis of Alkynes
• 9.10 Alkylation of Terminal Alkynes
• 9.11 Synthesis Strategies
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 10 Radical Reactions
• 10.1 Radicals
• 10.2 Common Patterns in Radical Mechanisms
• 10.3 Chlorination of Methane
• 10.4 Thermodynamic Considerations for Halogenation Reactions
• 10.5 Selectivity of Halogenation
• 10.6 Stereochemistry of Halogenation
• 10.7 Allylic Bromination
• 10.8 Atmospheric Chemistry and the Ozone Layer
• 10.9 Autooxidation and Antioxidants
• 10.10 Radical Addition of HBr: Anti-Markovnikov Addition
• 10.11 Radical Polymerization
• 10.12 Radical Processes in the Petrochemical Industry
• 10.13 Halogenation as a Synthetic Technique
• REVIEW OF CONCEPTS AND VOCABULARY
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• 11 Synthesis
• 11.1 One-Step Syntheses
• 11.2 Functional Group Transformations
• 11.3 Reactions That Change the Carbon Skeleton
• 11.4 How to Approach a Synthesis Problem
• 11.5 Multi-Step Synthesis and Retrosynthetic Analysis
• 11.6 Green Chemistry
• 11.7 Practical Tips for Increasing Proficiency
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 12 Alcohols and Phenols
• 12.1 Structure and Properties of Alcohols
• 12.2 Acidity of Alcohols and Phenols
• 12.3 Preparation of Alcohols via Substitution or Addition
• 12.4 Preparation of Alcohols via Reduction
• 12.5 Preparation of Diols
• 12.6 Preparation of Alcohols via Grignard Reagents
• 12.7 Protection of Alcohols
• 12.8 Preparation of Phenols
• 12.9 Reactions of Alcohols: Substitution and Elimination
• 12.10 Reactions of Alcohols: Oxidation
• 12.11 Biological Redox Reactions
• 12.12 Oxidation of Phenol
• 12.13 Synthesis Strategies
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 13 Ethers and Epoxides; Thiols and Sulfides
• 13.1 Introduction to Ethers
• 13.2 Nomenclature of Ethers
• 13.3 Structure and Properties of Ethers
• 13.4 Crown Ethers
• 13.5 Preparation of Ethers
• 13.6 Reactions of Ethers
• 13.7 Nomenclature of Epoxides
• 13.8 Preparation of Epoxides
• 13.9 Enantioselective Epoxidation
• 13.10 Ring-Opening Reactions of Epoxides
• 13.11 Thiols and Sulfides
• 13.12 Synthesis Strategies Involving Epoxides
• REVIEW OF CONCEPTS AND VOCABULARY
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• 14 Infrared Spectroscopy and Mass Spectrometry
• 14.1 Introduction to Spectroscopy
• 14.2 IR Spectroscopy
• 14.3 Signal Characteristics: Wavenumber
• 14.4 Signal Characteristics: Intensity
• 14.5 Signal Characteristics: Shape
• 14.6 Analyzing an IR Spectrum
• 14.7 Using IR Spectroscopy to Distinguish between Two Compounds
• 14.8 Introduction to Mass Spectrometry
• 14.9 Analyzing the (M)+• Peak
• 14.10 Analyzing the (M+1)+• Peak
• 14.11 Analyzing the (M+2)+• Peak
• 14.12 Analyzing the Fragments
• 14.13 High-Resolution Mass Spectrometry
• 14.14 Gas Chromatography–Mass Spectrometry
• 14.15 Mass Spectrometry of Large Biomolecules
• 14.16 Hydrogen Deficiency Index: Degrees of Unsaturation
• REVIEW OF CONCEPTS AND VOCABULARY
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• 15 Nuclear Magnetic Resonance Spectroscopy
• 15.1 Introduction to NMR Spectroscopy
• 15.2 Acquiring a 1H NMR Spectrum
• 15.3 Characteristics of a 1H NMR Spectrum
• 15.4 Number of Signals
• 15.5 Chemical Shift
• 15.6 Integration
• 15.7 Multiplicity
• 15.8 Drawing the Expected 1H NMR Spectrum of a Compound
• 15.9 Using 1H NMR Spectroscopy to Distinguish between Compounds
• 15.10 Analysing a 1H NMR Spectrum
• 15.11 Acquiring a 13C NMR Spectrum
• 15.12 Chemical Shifts in 13C NMR Spectroscopy
• 15.13 DEPT 13C NMR Spectroscopy
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 16 Conjugated Pi Systems and Pericyclic Reactions
• 16.1 Classes of Dienes
• 16.2 Conjugated Dienes
• 16.3 Molecular Orbital Theory
• 16.4 Electrophilic Addition
• 16.5 Thermodynamic Control vs. Kinetic Control
• 16.6 An Introduction to Pericyclic Reactions
• 16.7 Diels–Alder Reactions
• 16.8 MO Description of Cycloadditions
• 16.9 Electrocyclic Reactions
• 16.10 Sigmatropic Rearrangements
• 16.11 UV-Vis Spectroscopy
• 16.12 Color
• 16.13 Chemistry of Vision
• REVIEW OF CONCEPTS AND VOCABULARY
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• 17 Aromatic Compounds
• 17.1 Introduction to Aromatic Compounds
• 17.2 Nomenclature of Benzene Derivatives
• 17.3 Structure of Benzene
• 17.4 Stability of Benzene
• 17.5 Aromatic Compounds Other Than Benzene
• 17.6 Reactions at the Benzylic Position
• 17.7 Reduction of Benzene and Its Derivatives
• 17.8 Spectroscopy of Aromatic Compounds
• REVIEW OF CONCEPTS AND VOCABULARY
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• 18 Aromatic Substitution Reactions
• 18.1 Introduction to Electrophilic Aromatic Substitution
• 18.2 Halogenation
• 18.3 Sulfonation
• 18.4 Nitration
• 18.5 Friedel–Crafts Alkylation
• 18.6 Friedel–Crafts Acylation
• 18.7 Activating Groups
• 18.8 Deactivating Groups
• 18.9 Halogens: The Exception
• 18.10 Determining the Directing Effects of a Substituent
• 18.11 Multiple Substituents
• 18.12 Synthesis Strategies
• 18.13 Nucleophilic Aromatic Substitution
• 18.14 Elimination-Addition
• 18.15 Identifying the Mechanism of an Aromatic Substitution Reaction
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• 19 Aldehydes and Ketones
• 19.1 Introduction to Aldehydes and Ketones
• 19.2 Nomenclature
• 19.3 Preparing Aldehydes and Ketones: A Review
• 19.4 Introduction to Nucleophilic Addition Reactions
• 19.5 Oxygen Nucleophiles
• 19.6 Nitrogen Nucleophiles
• 19.7 Hydrolysis of Acetals, Imines, and Enamines
• 19.8 Sulfur Nucleophiles
• 19.9 Hydrogen Nucleophiles
• 19.10 Carbon Nucleophiles
• 19.11 Baeyer– Villiger Oxidation of Aldehydes and Ketones
• 19.12 Synthesis Strategies
• 19.13 Spectroscopic Analysis of Aldehydes and Ketones
• REVIEW OF CONCEPTS AND VOCABULARY
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• PRACTICE PROBLEMS
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• 20 Carboxylic Acids and Their Derivatives
• 20.1 Introduction to Carboxylic Acids
• 20.2 Nomenclature of Carboxylic Acids
• 20.3 Structure and Properties of Carboxylic Acids
• 20.4 Preparation of Carboxylic Acids
• 20.5 Reactions of Carboxylic Acids
• 20.6 Introduction to Carboxylic Acid Derivatives
• 20.7 Reactivity of Carboxylic Acid Derivatives
• 20.8 Preparation and Reactions of Acid Chlorides
• 20.9 Preparation and Reactions of Acid Anhydrides
• 20.10 Preparation of Esters
• 20.11 Reactions of Esters
• 20.12 Preparation and Reactions of Amides
• 20.13 Preparation and Reactions of Nitriles
• 20.14 Synthesis Strategies
• 20.15 Spectroscopy of Carboxylic Acids and Their Derivatives
• REVIEW OF CONCEPTS AND VOCABULARY
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• 21 Alpha Carbon Chemistry: Enols and Enolates
• 21.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates
• 21.2 Alpha Halogenation of Enols and Enolates
• 21.3 Aldol Reactions
• 21.4 Claisen Condensations
• 21.5 Alkylation of the Alpha Position
• 21.6 Conjugate Addition Reactions
• 21.7 Synthesis Strategies
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• 22 Amines
• 22.1 Introduction to Amines
• 22.2 Nomenclature of Amines
• 22.3 Properties of Amines
• 22.4 Preparation of Amines: A Review
• 22.5 Preparation of Amines via Substitution Reactions
• 22.6 Preparation of Amines via Reductive Amination
• 22.7 Synthesis Strategies
• 22.8 Acylation of Amines
• 22.9 Hofmann Elimination
• 22.10 Reactions of Amines with Nitrous Acid
• 22.11 Reactions of Aryl Diazonium Ions
• 22.12 Nitrogen Heterocycles
• 22.13 Spectroscopy of Amines
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• 23 Introduction to Organometallic Compounds
• 23.1 General Properties of Organometallic Compounds
• 23.2 Organolithium and Organomagnesium Compounds
• 23.3 Lithium Dialkyl Cuprates (Gilman Reagents)
• 23.4 The Simmons—Smith Reaction and Carbenoids
• 23.5 Stille Coupling
• 23.6 Suzuki Coupling
• 23.7 Negishi Coupling
• 23.8 The Heck Reaction
• 23.9 Alkene Metathesis
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• 24 Carbohydrates
• 24.1 Introduction to Carbohydrates
• 24.2 Classification of Monosaccharides
• 24.3 Configuration of Aldoses
• 24.4 Configuration of Ketoses
• 24.5 Cyclic Structures of Monosaccharides
• 24.6 Reactions of Monosaccharides
• 24.7 Disaccharides
• 24.8 Polysaccharides
• 24.9 Amino Sugars
• 24.10 N-Glycosides
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• 25 Amino Acids, Peptides, and Proteins
• 25.1 Introduction to Amino Acids, Peptides, and Proteins
• 25.2 Structure and Properties of Amino Acids
• 25.3 Amino Acid Synthesis
• 25.4 Structure of Peptides
• 25.5 Sequencing a Peptide
• 25.6 Peptide Synthesis
• 25.7 Protein Structure
• 25.8 Protein Function
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• 26 Lipids
• 26.1 Introduction to Lipids
• 26.2 Waxes
• 26.3 Triglycerides
• 26.4 Reactions of Triglycerides
• 26.5 Phospholipids
• 26.6 Steroids
• 26.7 Prostaglandins
• 26.8 Terpenes
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• 27 Synthetic Polymers
• 27.1 Introduction to Synthetic Polymers
• 27.2 Nomenclature of Synthetic Polymers
• 27.3 Copolymers
• 27.4 Polymer Classification by Reaction Type
• 27.5 Polymer Classification by Mode of Assembly
• 27.6 Polymer Classification by Structure
• 27.7 Polymer Classification by Properties
• 27.8 Polymer Recycling
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• Appendix: Nomenclature of Polyfunctional Compounds
• Glossary
• Index
• End User License Agreement