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FSU CHM2210: Zhu

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    Honors Organic Chemistry I (CHM2210)  
    Chapter references are for "Organic Chemistry" by Carey and Guiliano
    Dr. Lei Zhu

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    CHAPTER 1: Structure Determines Properties

    1.1 Atoms, Electrons, and Orbitals
    1.2 Ionic Bonds
    1.3 Covalent Bonds, Lewis Structures, and the Octet Rule
    1.4 Double Bonds and Triple Bonds
    1.5 Polar Covalent Bonds and Electronegativity
    Electrostatic Potential Maps
    1.6 Structural Formulas of Organic Molecules
    1.7 Formal Charge
    1.8 Resonance
    1.9 The Shapes of Some Simple Molecules
    Molecular Modeling
    1.10 Molecular Dipole Moments
    1.11 Curved Arrows and Chemical Reactions
    1.12 Acids and Bases: The Arrhenius View
    1.13 Acids and Bases: The Brønsted–Lowry View
    1.14 What Happened to pKb?
    1.15 How Structure Affects Acid Strength
    1.16 Acid–Base Equilibria
    1.17 Lewis Acids and Lewis Bases
    1.18 Summary
    Descriptive Passage and Interpretive Problems 1: Amide Lewis Structures

    CHAPTER 2: Alkanes and Cycloalkanes: Introduction to Hydrocarbons

    2.1 Classes of Hydrocarbons
    2.2 Electron Waves and Chemical Bonds
    2.3 Bonding in H2: The Valence Bond Model
    2.4 Bonding in H2: The Molecular Orbital Model
    2.5 Introduction to Alkanes: Methane, Ethane, and Propane Methane and the Biosphere
    2.6 sp3 Hybridization and Bonding in Methane
    2.7 Bonding in Ethane
    2.8 Isomeric Alkanes: The Butanes
    2.9 Higher n-Alkanes
    2.10 The C5H12 Isomers
    2.11 IUPAC Nomenclature of Unbranched Alkanes
    What's in a Name: Organic Nomenclature
    2.12 Applying the IUPAC Rules: The Names of the C6H14 Isomers
    2.13 Alkyl Groups
    2.14 IUPAC Names of Highly Branched Alkanes
    2.15 Cycloalkane Nomenclature
    2.16 Sources of Alkanes and Cycloalkanes
    2.17 Physical Properties of Alkanes and Cycloalkanes
    2.18 Chemical Properties: Combustion of Alkanes
    2.19 Oxidation–Reduction in Organic Chemistry Thermochemistry
    2.20 sp2 Hybridization and Bonding in Ethylene
    2.21 sp Hybridization and Bonding in Acetylene
    2.22 Which Theory of Chemical Bonding Is Best?
    2.23 Summary
    Descriptive Passage and Interpretive Problems 2: Some Biochemical Reactions of Alkanes

    CHAPTER 3: Alkanes and Cycloalkanes: Conformations and cis–trans Stereoisomers

    3.1 Conformational Analysis of Ethane
    3.2 Conformational Analysis of Butane
    Molecular Mechanics Applied to Alkanes and Cycloalkanes 109 3.3 Conformations of Higher Alkanes
    3.4 The Shapes of Cycloalkanes: Planar or Nonplanar?
    3.5 Small Rings: Cyclopropane and Cyclobutane
    3.6 Cyclopentane
    3.7 Conformations of Cyclohexane
    3.8 Axial and Equatorial Bonds in Cyclohexane
    3.9 Conformational Inversion (Ring Flipping) in Cyclohexane
    3.10 Conformational Analysis of Monosubstituted Cyclohexanes
    3.11 Disubstituted Cycloalkanes: cis-trans Stereoisomers
    Enthalpy, Free Energy, and Equilibrium Constant
    3.12 Conformational Analysis of Disubstituted Cyclohexanes
    3.13 Medium and Large Rings
    3.14 Polycyclic Ring Systems
    3.15 Heterocyclic Compounds
    3.16 Summary
    Descriptive Passage and Interpretive Problems 3: Forms of carbohydrates

    CHAPTER 4: Alcohols and Alkyl Halides

    4.1 Functional Groups
    4.2 IUPAC Nomenclature of Alkyl Halides
    4.3 IUPAC Nomenclature of Alcohols
    4.4 Classes of Alcohols and Alkyl Halides
    4.5 Bonding in Alcohols and Alkyl Halides
    4.6 Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces
    4.7 Preparation of Alkyl Halides from Alcohols and Hydrogen Halides
    4.8 Mechanism of the Reaction of Alcohols with Hydrogen Halides
    4.9 Potential Energy Diagrams for Multistep Reactions: The SN1 Mechanism
    4.10 Structure, Bonding, and Stability of Carbocations
    4.11 Effect of Alcohol Structure on Reaction Rate
    4.12 Reaction of Methyl and Primary Alcohols with Hydrogen Halides: The SN2 Mechanism
    4.13 Other Methods for Converting Alcohols to Alkyl Halides
    4.14 Halogenation of Alkanes
    4.15 Chlorination of Methane
    4.16 Structure and Stability of Free Radicals
    4.17 Mechanism of Methane Chlorination
    4.18 Halogenation of Higher Alkanes
    From Bond Energies to Heats of Reaction
    4.19 Summary
    Descriptive Passage and Interpretive Problems 4: More About Potential Energy Diagrams

    CHAPTER 5: Structure and Preparation of Alkenes: Elimination Reactions

    5.1 Alkene Nomenclature
    5.2 Structure and Bonding in Alkenes
    5.3 Isomerism in Alkenes
    5.4 Naming Stereoisomeric Alkenes by the E–Z Notational System
    5.5 Physical Properties of Alkenes
    5.6 Relative Stabilities of Alkenes
    5.7 Cycloalkenes
    5.8 Preparation of Alkenes: Elimination Reactions
    5.9 Dehydration of Alcohols
    5.10 Regioselectivity in Alcohol Dehydration: The Zaitsev Rule
    5.11 Stereoselectivity in Alcohol Dehydration
    5.12 The E1 and E2 Mechanisms of Alcohol Dehydration
    5.13 Rearrangements in Alcohol Dehydration
    5.14 Dehydrohalogenation of Alkyl Halides
    5.15 The E2 Mechanism of Dehydrohalogenation of Alkyl Halides
    5.16 Anti Elimination in E2 Reactions: Stereoelectronic Effects
    5.17 Isotope Effects and the E2 Mechanism
    5.18 The E1 Mechanism of Dehydrohalogenation of Alkyl Halides
    5.19 Summary
    Descriptive Passage and Interpretive Problems 5: A Mechanistic Preview of Addition Reactions

    CHAPTER 6: Addition Reactions of Alkenes

    6.1 Hydrogenation of Alkenes
    6.2 Heats of Hydrogenation
    6.3 Stereochemistry of Alkene Hydrogenation
    6.4 Electrophilic Addition of Hydrogen Halides to Alkenes
    6.5 Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule
    6.6 Mechanistic Basis for Markovnikov’s Rule
    Rules, Laws, Theories, and the Scientific Method
    6.7 Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes
    6.8 Free-Radical Addition of Hydrogen Bromide to Alkenes
    6.9 Addition of Sulfuric Acid to Alkenes
    6.10 Acid-Catalyzed Hydration of Alkenes
    6.11 Thermodynamics of Addition–Elimination Equilibria
    6.12 Hydroboration–Oxidation of Alkenes
    6.13 Stereochemistry of Hydroboration–Oxidation
    6.14 Mechanism of Hydroboration–Oxidation
    6.15 Addition of Halogens to Alkenes
    6.16 Stereochemistry of Halogen Addition
    6.17 Mechanism of Halogen Addition to Alkenes: Halonium Ions
    6.18 Conversion of Alkenes to Vicinal Halohydrins
    6.19 Epoxidation of Alkenes
    6.20 Ozonolysis of Alkenes
    6.21 Introduction to Organic Chemical Synthesis
    6.22 Reactions of Alkenes with Alkenes: Polymerization
    Ethylene and Propene: The Most Important Industrial Organic Chemicals
    6.23 Summary
    Descriptive Passage and Interpretive Problems 6: Some Unusual Electrophilic Additions

    CHAPTER 7: Stereochemistry

    7.1 Molecular Chirality: Enantiomers
    7.2 The Chirality Center
    7.3 Symmetry in Achiral Structures
    7.4 Optical Activity
    7.5 Absolute and Relative Configuration
    7.6 The Cahn–Ingold–Prelog R–S Notational System
    7.7 Fischer Projections
    7.8 Properties of Enantiomers
    Chiral Drugs
    7.9 Reactions That Create a Chirality Center
    7.10 Chiral Molecules with Two Chirality Centers
    7.11 Achiral Molecules with Two Chirality Centers
    7.12 Molecules with Multiple Chirality Centers
    Chirality of Disubstituted Cyclohexanes
    7.13 Reactions That Produce Diastereomers
    7.14 Resolution of Enantiomers
    7.15 Stereoregular Polymers
    7.16 Chirality Centers Other Than Carbon
    7.17 Summary
    Descriptive Passage and Interpretive Problems 7: Prochirality

    CHAPTER 8: Nucleophilic SubstitutionEdit section

    8.1 Functional Group Transformation by Nucleophilic Substitution
    8.2 Relative Reactivity of Halide Leaving Groups
    8.3 The SN2 Mechanism of Nucleophilic Substitution
    8.4 Steric Effects in SN2 Reaction Rates
    8.5 Nucleophiles and Nucleophilicity
    8.6 The SN1 Mechanism of Nucleophilic Substitution
    Enzyme-Catalyzed Nucleophilic Substitutions of Alkyl Halides
    8.7 Carbocation Stability and SN1 Reaction Rates
    8.8 Stereochemistry of SN1 Reactions
    8.9 Carbocation Rearrangements in SN 1 Reactions
    8.10 Effect of Solvent on the Rate of Nucleophilic Substitution
    8.11 Substitution and Elimination as Competing Reactions
    8.12 Nucleophilic Substitution of Alkyl Sulfonates
    8.13 Looking Back: Reactions of Alcohols with Hydrogen Halides
    8.14 Summary
    Descriptive Passage and Interpretive Problems 8: Nucleophilic Substitution

    CHAPTER 9: Alkynes

    9.1 Sources of Alkynes
    9.2 Nomenclature
    9.3 Physical Properties of Alkynes
    9.4 Structure and Bonding in Alkynes: sp Hybridization
    9.5 Acidity of Acetylene and Terminal Alkynes
    9.6 Preparation of Alkynes by Alkyation of Acetylene and Terminal Alkynes
    9.7 Preparation of Alkynes by Elimination Reactions
    9.8 Reactions of Alkynes
    9.9 Hydrogenation of Alkynes
    9.10 Metal–Ammonia Reduction of Alkynes
    9.11 Addition of Hydrogen Halides to Alkynes
    9.12 Hydration of Alkynes
    9.13 Addition of Halogens to Alkynes
    Some Things That Can Be Made from Acetylene...But Aren't
    9.14 Ozonolysis of Alkynes
    9.15 Summary
    Descriptive Passage and Interpretive Problems 9: Thinking Mechanistically About Alkynes

    CHAPTER 10: Conjugation in Alkadienes and Allylic Systems

    10.1 The Allyl Group
    10.2 Allylic Carbocations
    10.3 SN1 Reactions of Allylic Halides
    10.4 SN2 Reactions of Allylic Halides
    10.5 Allylic Free Radicals
    10.6 Allylic Halogenation
    10.7 Allylic Anions
    10.8 Classes of Dienes
    10.9 Relative Stabilities of Dienes
    10.10 Bonding in Conjugated Dienes
    10.11 Bonding in Allenes
    10.12 Preparation of Dienes
    10.13 Addition of Hydrogen Halides to Conjugated Dienes
    10.14 Halogen Addition to Dienes
    10.15 The Diels–Alder Reaction
    Diene Polymers
    10.16 The Pi Molecular Orbitals of Ethylene and 1,3-Butadiene
    10.17 A Pi Molecular Orbital Analysis of the Diels–Alder Reaction
    10.18 Summary
    Descriptive Passage and Interpretive Problems 10: Intramolecular and Retro Diels-Alder Reactions