Organic Chemistry 1st edition


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  • Chapter T: Tutorial
    • Tutorial (11)

  • Chapter 1: A Review of General Chemistry: Electrons, Bonds, and Molecular Properties
    • 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: Atomic Orbitals
    • 1.7: Valence Bond Theory
    • 1.8: Molecular Orbital Theory
    • 1.9: Hybridized Atomic Orbitals
    • 1.10: VSEPR Theory: Predicting Geometry
    • 1.11: Dipole Moments and Molecular Polarity
    • 1.12: Intermolecular Forces and Physical Properties
    • 1.13: Solubility
    • 1: Practice Problems (12)
    • 1: Extra Problems

  • Chapter 2: Molecular Representations
    • 2.1: Molecular Representations
    • 2.2: 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 Relative Importance of Resonance Structures
    • 2.12: Delocalized and Localized Lone Pairs
    • 2: Practice Problems (12)
    • 2: Extra Problems

  • Chapter 3: Acids and Bases
    • 3.1: An Introduction to BrØnsted-Lowry Acids and Bases
    • 3.2: Flow of Electron Density: Curved Arrow Notation
    • 3.3: BrØnsted-Lowry Acidity: A Quantitative Perspective
    • 3.4: BrØnsted-Lowry Acidity: Qualitative Perspective
    • 3.5: Position of Equilibrium and Choice of Reagents
    • 3.6: Choice of Solvent
    • 3.7: Solvating Effects
    • 3.8: Counterions
    • 3.9: Lewis Acids and Bases
    • 3: Practice Problems (14)
    • 3: Extra Problems

  • Chapter 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
    • 4: Practice Problems (28)
    • 4: Extra Problems

  • Chapter 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: Resolution of Enantiomers
    • 5: Practice Problems (14)
    • 5: Extra Problems

  • Chapter 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: Practice Problems (13)
    • 6: Extra Problems

  • Chapter 7: Substitution Reactions
    • 7.1: Introduction to Substitution Reactions
    • 7.2: Alkyl Halides
    • 7.3: Possible Mechanisms for Substitution Reactions
    • 7.4: The SN2 Mechanism
    • 7.5: The SN1 Mechanism
    • 7.6: Drawing the Complete Mechanism of an SN1 Reaction
    • 7.7: Drawing the Complete Mechanism of an SN2 Reaction
    • 7.8: Determining Which Mechanism Predominates
    • 7.9: Selecting Reagents to Accomplish Functional Group Transformation
    • 7: Practice Problems (24)
    • 7: Extra Problems

  • Chapter 8: Alkenes: Structure and Preparation via Elimination Reactions
    • 8.1: Introduction to Elimination Reactions
    • 8.2: Alkenes in Nature and in Industry
    • 8.3: Nomenclature of Alkenes
    • 8.4: Stereoisomerism in Alkenes
    • 8.5: Alkene Stability
    • 8.6: Possible Mechanisms for Elimination
    • 8.7: The E2 Mechanism
    • 8.8: Drawing the Products of an E2 Reaction
    • 8.9: The E1 Mechanism
    • 8.10: Drawing the Complete Mechanism of an E1 Process
    • 8.11: Drawing the Complete Mechanism of an E2 Process 372
    • 8.12: Substitution vs. Elimination: Identifying the Reagent
    • 8.13: Substitution vs. Elimination: Identifying the Mechanism(s)
    • 8.14: Substitution vs. Elimination: Predicting the Products
    • 8: Practice Problems (25)
    • 8: Extra Problems

  • Chapter 9: Addition Reactions of Alkenes
    • 9.1: Introduction to Addition Reactions
    • 9.2: Addition vs. Elimination: A Thermodynamic Perspective
    • 9.3: Hydrohalogenation
    • 9.4: Acid-Catalyzed Hydration
    • 9.5: Oxymercuration-Demercuration
    • 9.6: Hydroboration-Oxidation
    • 9.7: Catalytic Hydrogenation
    • 9.8: Halogenation and Halohydrin Formation
    • 9.9: Anti Dihydroxylation
    • 9.10: Syn Dihydroxylation
    • 9.11: Oxidative Cleavage
    • 9.12: Predicting Products of an Addition Reaction
    • 9.13: Synthesis Strategies
    • 9: Practice Problems (23)
    • 9: Extra Problems

  • Chapter 10: Alkynes
    • 10.1: Introduction to Alkynes
    • 10.2: Nomenclature of Alkynes
    • 10.3: Acidity of Acetylene and Terminal Alkynes
    • 10.4: Preparing Alkynes
    • 10.5: Reduction of Alkynes
    • 10.6: Hydrohalogenation of Alkynes
    • 10.7: Hydration of Alkynes
    • 10.8: Halogenation of Alkynes
    • 10.9: Ozonolysis of Alkynes
    • 10.10: Alkylation of Terminal Alkynes
    • 10.11: Synthesis Strategies
    • 10: Practice Problems (14)
    • 10: Extra Problems

  • Chapter 11: Radical Reactions
    • 11.1: Radicals
    • 11.2: Common Patterns in Radical Mechanisms
    • 11.3: Chlorination of Methane
    • 11.4: Thermodynamic Considerations for Halogenation Reactions
    • 11.5: Regioselectivity of Halogenation
    • 11.6: Stereochemistry of Halogenation
    • 11.7: Allylic Bromination
    • 11.8: Atmospheric Chemistry and the Ozone Layer
    • 11.9: Autooxidation and Antioxidants
    • 11.10: Addition of HBr: Anti-Markovnikov Addition
    • 11.11: Radical Polymerization
    • 11.12: Radical Processes in the Petrochemical Industry
    • 11.13: Halogenation as a Synthetic Technique
    • 11: Practice Problems (10)
    • 11: Extra Problems

  • Chapter 12: Synthesis
    • 12.1: One-Step Syntheses
    • 12.2: Functional Group Transformations
    • 12.3: Reactions that Change the Carbon Skeleton
    • 12.4: How to Approach a Synthesis Problem
    • 12.5: Retrosynthetic Analysis
    • 12.6: Practical Tips for Increasing Proficiency
    • 12: Practice Problems (3)
    • 12: Extra Problems

  • Chapter 13: Alcohols and Phenols
    • 13.1: Structure and Properties of Alcohols
    • 13.2: Acidity of Alcohols and Phenols
    • 13.3: Preparation of Alcohols via Substitution or Addition
    • 13.4: Preparation of Alcohols via Reduction
    • 13.5: Preparation of Diols
    • 13.6: Preparation of Alcohols via Grignard Reagents
    • 13.7: Protection of Alcohols
    • 13.8: Preparation of Phenols
    • 13.9: Reactions of Alcohols: Substitution and Elimination
    • 13.10: Reactions of Alcohols: Oxidation
    • 13.11: Biological Redox Reactions
    • 13.12: Oxidation of Phenol
    • 13.13: Synthesis Strategies
    • 13: Practice Problems (25)
    • 13: Extra Problems

  • Chapter 14: Ethers and Epoxides; Thiols and Sulfides
    • 14.1: Introduction to Ethers
    • 14.2: Nomenclature of Ethers
    • 14.3: Structure and Properties of Ethers
    • 14.4: Crown Ethers
    • 14.5: Preparation of Ethers
    • 14.6: Reactions of Ethers
    • 14.7: Nomenclature of Epoxides
    • 14.8: Preparation of Epoxides
    • 14.9: Enantioselective Epoxidation
    • 14.10: Ring-Opening Reactions of Epoxides
    • 14.11: Thiols and Sulfides
    • 14.12: Synthesis Strategies Involving Epoxides
    • 14: Practice Problems (9)
    • 14: Extra Problems

  • Chapter 15: Infrared Spectroscopy and Mass Spectrometry
    • 15.1: Introduction to Spectroscopy
    • 15.2: IR Spectroscopy
    • 15.3: Signal Characteristics: Wavenumber
    • 15.4: Signal Characteristics: Intensity
    • 15.5: Signal Characteristics: Shape
    • 15.6: Analyzing an IR Spectrum
    • 15.7: Using IR Spectroscopy to Distinguish between Two Compounds
    • 15.8: Introduction to Mass Spectrometry
    • 15.9: Analyzing the (M)+• Peak
    • 15.10: Analyzing the (M+1) +• Peak
    • 15.11: Analyzing the (M+2) +• Peak
    • 15.12: Analyzing the Fragments
    • 15.13: High Resolution Mass Spectrometry
    • 15.14: Gas Chromatography—Mass Spectrometry
    • 15.15: Mass Spectrometry of Large Biomolecules
    • 15.16: Hydrogen Deficiency Index: Degrees of Unsaturation
    • 15: Practice Problems (13)
    • 15: Extra Problems

  • Chapter 16: Nuclear Magnetic Resonance Spectroscopy
    • 16.1: Introduction to NMR Spectroscopy
    • 16.2: Acquiring a 1H NMR Spectrum
    • 16.3: Characteristics of a 1H NMR Spectrum
    • 16.4: Number of Signals
    • 16.5: Chemical Shift
    • 16.6: Integration
    • 16.7: Multiplicity
    • 16.8: Drawing the Expected 1H NMR Spectrum of a Compound
    • 16.9: Using 1H NMR Spectroscopy to Distinguish between Compounds
    • 16.10: Analyzing a 1H NMR Spectrum
    • 16.11: Acquiring a 13C NMR Spectrum
    • 16.12: Chemical Shifts in 13C NMR Spectroscopy
    • 16.13: DEPT 13C NMR Spectroscopy
    • 16: Practice Problems (15)
    • 16: Extra Problems

  • Chapter 17: Conjugated Pi Systems and Pericyclic Reactions
    • 17.1: Classes of Dienes
    • 17.2: Conjugated Dienes
    • 17.3: Molecular Orbital Theory
    • 17.4: Electrophilic Addition
    • 17.5: Thermodynamic Control vs. Kinetic Control
    • 17.6: An Introduction to Pericyclic Reactions
    • 17.7: Diels—Alder Reactions
    • 17.8: MO Description of Cycloadditions
    • 17.9: Electrocyclic Reactions
    • 17.10: Sigmatropic Rearrangements
    • 17.11: UV-VIS Spectroscopy
    • 17.12: Color 806
    • 17.13: The Chemistry of Vision
    • 17: Practice Problems (26)
    • 17: Extra Problems

  • Chapter 18: Aromatic Compounds
    • 18.1: Introduction to Aromatic Compounds
    • 18.2: Nomenclature of Benzene Derivatives
    • 18.3: Structure of Benzene
    • 18.4: Stability of Benzene
    • 18.5: Aromatic Compounds Other than Benzene
    • 18.6: Reactions at the Benzylic Position
    • 18.7: Reduction of the Aromatic Moiety
    • 18.8: Spectroscopy of Aromatic Compounds
    • 18: Practice Problems (11)
    • 18: Extra Problems

  • Chapter 19: Aromatic Substitution Reactions
    • 19.1: Introduction to Electrophilic Aromatic Substitution
    • 19.2: Halogenation
    • 19.3: Sulfonation
    • 19.4: Nitration
    • 19.5: Friedel-Crafts Alkylation
    • 19.6: Friedel-Crafts Acylation
    • 19.7: Activating Groups
    • 19.8: Deactivating Groups
    • 19.9: Halogens: The Exception
    • 19.10: Determining the Directing Effects of a Substituent
    • 19.11: Multiple Substituents
    • 19.12: Synthesis Strategies
    • 19.13: Nucleophilic Aromatic Substitution
    • 19.14: Elimination-Addition
    • 19.15 Identifying the Mechanism of an Aromatic Substitution Reaction
    • 19: Practice Problems (23)
    • 19: Extra Problems

  • Chapter 20: Aldehydes and Ketones
    • 20.1: Introduction to Aldehydes and Ketones
    • 20.2: Nomenclature
    • 20.3: Preparing Aldehydes and Ketones: A Review
    • 20.4: Introduction to Nucleophilic Addition Reactions
    • 20.5: Oxygen Nucleophiles
    • 20.6: Nitrogen Nucleophiles
    • 20.7: Mechanism Strategies
    • 20.8: Sulfur Nucleophiles
    • 20.9: Hydrogen Nucleophiles
    • 20.10: Carbon Nucleophiles
    • 20.11: Baeyer-Villiger Oxidation of Aldehydes and Ketones
    • 20.12: Synthesis Strategies
    • 20.13: Spectroscopic Analysis of Aldehydes and Ketones
    • 20: Practice Problems (16)
    • 20: Extra Problems

  • Chapter 21: Carboxylic Acids and Their Derivatives
    • 21.1: Introduction to Carboxylic Acids
    • 21.2: Nomenclature of Carboxylic Acids
    • 21.3: Structure and Properties of Carboxylic Acids
    • 21.4: Preparation of Carboxylic Acids
    • 21.5: Reactions of Carboxylic Acids
    • 21.6: Introduction to Carboxylic Acid Derivatives
    • 21.7: Reactivity of Carboxylic Acid Derivatives
    • 21.8: Preparation and Reactions of Acid Chlorides
    • 21.9: Preparation and Reactions of Acid Anhydrides
    • 21.10: Preparation of Esters
    • 21.11: Reactions of Esters
    • 21.12: Preparation and Reactions of Amides
    • 21.13: Preparation and Reactions of Nitriles
    • 21.14: Synthesis Strategies
    • 21.15: Spectroscopy of Carboxylic Acids and Their Derivatives
    • 21: Practice Problems (32)
    • 21: Extra Problems

  • Chapter 22: Alpha Carbon Chemistry: Enols and Enolates
    • 22.1: Introduction to Alpha Carbon Chemistry: Enols and Enolates
    • 22.2: Alpha Halogenation of Enols and Enolates
    • 22.3: Aldol Reactions
    • 22.4: Claisen Condensations
    • 22.5: Alkylation of the Alpha Position
    • 22.6: Conjugate Addition Reactions
    • 22.7: Synthesis Strategies
    • 22: Practice Problems (23)
    • 22: Extra Problems

  • Chapter 23: Amines
    • 23.1: Introduction to Amines
    • 23.2: Nomenclature of Amines
    • 23.3: Properties of Amines
    • 23.4: Preparation of Amines: A Review
    • 23.5: Preparation of Amines via Substitution Reactions
    • 23.6: Preparation of Amines via Reductive Amination
    • 23.7: Synthesis Strategies
    • 23.8: Acylation of Amines
    • 23.9: The Hofmann Elimination
    • 23.10: Reactions of Amines with Nitrous Acid
    • 23.11: Reactions of Aryldiazonium Ions
    • 23.12: Nitrogen Heterocycles
    • 23.13: Spectroscopy of Amines
    • 23: Practice Problems (27)
    • 23: Extra Problems

  • Chapter 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
    • 24: Practice Problems (12)
    • 24: Extra Problems

  • Chapter 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
    • 25: Practice Problems (10)
    • 25: Extra Problems

  • Chapter 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
    • 26: Practice Problems (11)
    • 26: Extra Problems

  • Chapter 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
    • 27: Practice Problems (7)
    • 27: Extra Problems

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Chapter T: Tutorial
T.template 9 complete.mrv condensed.mrv lewis.mrv reaction.mrv reaction_adv.mrv resonance.mrv skeleton.mrv skeleton_adv.mrv splitarray.mrv
T.tutorial 2 lewis.structures marvinsketch.introduction
Chapter 1: A Review of General Chemistry: Electrons, Bonds, and Molecular Properties
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Chapter 2: Molecular Representations
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Chapter 3: Acids and Bases
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Chapter 4: Alkanes and Cycloalkanes
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Chapter 5: Stereoisomerism
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Chapter 6: Chemical Reactivity and Mechanisms
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Chapter 7: Substitution Reactions
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Chapter 8: Alkenes: Structure and Preparation via Elimination Reactions
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Chapter 9: Addition Reactions of Alkenes
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Chapter 10: Alkynes
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Chapter 11: Radical Reactions
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Chapter 12: Synthesis
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Chapter 13: Alcohols and Phenols
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Chapter 14: Ethers and Epoxides; Thiols and Sulfides
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Chapter 15: Infrared Spectroscopy and Mass Spectrometry
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Chapter 16: Nuclear Magnetic Resonance Spectroscopy
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Chapter 17: Conjugated Pi Systems and Pericyclic Reactions
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Chapter 18: Aromatic Compounds
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Chapter 19: Aromatic Substitution Reactions
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Chapter 20: Aldehydes and Ketones
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Chapter 21: Carboxylic Acids and Their Derivatives
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Chapter 22: Alpha Carbon Chemistry: Enols and Enolates
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Chapter 23: Amines
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Chapter 24: Carbohydrates
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Chapter 25: Amino Acids, Peptides, and Proteins
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Chapter 26: Lipids
26.P 11 001.XP 002.XP 003.XP.alt 004.XP 005.XP.alt 007.XP 008.XP 009.XP 011.XP 012.XP 013.XP
Chapter 27: Synthetic Polymers
27.P 7 001.XP 002.XP 003.XP 004.XP.alt 005.XP 006.XP.alt 007.XP
Total 463