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Structure and Bonding

  1. Valency and Formal Charges in Organic Chemistry
  2. Lewis Structures in Organic Chemistry
  3. Hybridization in Organic Chemistry
  4. Molecular and Electron Geometry of Organic Molecules
  5. Condensed Structures

Molecular Representations

  1. Bond-Line or Skeletal Structures
  2. Functional Groups in Organic Chemistry
  3. Converting between Bond-line, Lewis and Condensed structures
  4. Curved Arrows
  5. Resonance Structures in Organic Chemistry
  6. Assessing the Relative Importance of Resonance Structures
  7. Drawing Complex Patterns in Resonance Structures
  8. Localized and Delocalized Lone Pairs

Acids and Bases

  1. Organic Acids and Bases
  2. Organic acid-base mechanisms
  3. Acid Strength and pKa
  4. How to Determine the Position of Equilibrium for an Acid–Base Reaction
  5. Factors That Determine Acid Strength
  6. How to Choose an Acid or a Base to Protonate or Deprotonate a Given Compound
  7. Lewis Acids and Bases

Alkanes and Cycloalkanes

  1. Introduction to Alkanes
  2. Nomenclature of Alkanes
  3. Isomerism
  4. Constitutional or Structural Isomers
  5. Newman Projections
  6. Cycloalkanes
  7. Drawing the Chair Conformation of Cyclohexane
  8. Ring Flip: Drawing Both Chair Conformations
  9. Ring-Flip: Comparing the Stability of Chair Conformations
  10. Cis and Trans Decalin

Stereochemistry

  1. Stereoisomerism
  2. Chirality and Enantiomers
  3. The R and S system to label chiral centers
  4. Diastereomers
  5. Optical Activity
  6. Enantiomeric excess (ee)
  7. Calculating Enantiomeric Excess from Optical Activity
  8. Symmetry and Chiralty. Meso Compunds
  9. Fischer projection
  10. Resolution of Enantiomers

Chemical Reactivity and Mechanisms

Nucleophilic Substitution Reactions

  1. Introduction to Alkyl Halides
  2. Nomenclature of Alkyl Halides
  3. Introduction to Substitution Reactions
  4. The SN2 Mechanism
  5. The SN1 Mechanism
  6. The Substrate and Nucleophile in SN2 and SN1 Reactions
  7. The Role of the Solvent in SN1 and SN2 Reactions
  8. Carbocation Rearrangements in SN1 Reactions
  9. When Is the Mechanism SN1 or SN2?
  10. Selecting Reagents to Accomplish Functional Group Transformation
  11. Alcohols in Substitution Reactions

Alkenes: Structure, Stability and Nomenclature

Elimination Reactions

  1. General Features of Elimination
  2. The E2 Mechanism
  3. Regioselectivity of E2 Reactions: The Zaitsev and Hofmann Products
  4. Stereoselectivity of E2 Reactions
  5. Stereospecificity of E2 Reactions
  6. Elimination Reactions of Cyclohexanes
  7. The E1 Mechanism
  8. Stereoselectivity of E1 Reactions
  9. Nucleophilic Substitution vs Elimination Reactions
  10. Regioselectivity of E1 Reactions
  11. E2 vs. E1 Mechanism

Addition Reactions of Alkenes

  1. Hydrohalogenation: Regioselectivity-Markovnikov’s Rule
  2. Free-Radical Addition of HBr: Anti-Markovnikov Addition
  3. Addition of Water: Hydration of Alkenes
  4. Oxymercuration-Demercuration
  5. Hydroboration-Oxidation: The Mechanism
  6. The Regio- and Stereochemistry of Hydroboration-Oxidation
  7. Halogenation of Alkenes and Halohydrin Formation
  8. Ozonolysis of Alkenes
  9. Syn Dihydroxylation of Alkenes with KMnO4 and OsO4
  10. Anti Dihydroxylation of Alkenes with MCPBA and Other Peroxides
  11. Alkene Reactions Practice Problems
  12. Changing the Position of a Double Bond
  13. Changing the Position of a Leaving Group
  14. Alkenes Multi-Step Synthesis Practice Problems
  15. Addition of Alcohols to Alkenes

Alkynes

  1. Introduction to Alkynes
  2. Nomenclature of Alkynes
  3. Preparation of Alkynes by Elimination Reactions
  4. Hydrohalogenation of Alkynes
  5. Acid Catalyzed Hydration of Alkynes
  6. Reduction of Alkynes
  7. Halogenation of Alkynes
  8. Hydroboration-Oxidation of Alkynes
  9. Ozonolysis of Alkynes
  10. Alkylation of Terminal Alkynes
  11. Alkyne Synthesis Reactions Practice Problems

Organic Structure Determination

  1. Infrared (IR) Spectroscopy

Nuclear Magnetic Resonance (NMR) Spectroscopy

Radical Reactions

  1. Free-Radical Addition of HBr: Anti-Markovnikov Addition
  2. Initiation Propagation Termination in Radical Reactions
  3. Selectivity in Radical Halogenation
  4. Stability of Radicals
  5. Resonance Structures of Radicals
  6. Stereochemistry of Radical Halogenation
  7. Allylic Bromination
  8. Radical Halogenation in Organic Synthesis

Alcohols

  1. Alcohols in Substitution Reactions
  2. Nomenclature of Alcohols
  3. Preparation of Alcohols via Substitution or Addition Reactions
  4. Preparation of Alcohols by Reduction of Carbonyl Compounds
  5. Grignard Reaction in Preparing Alcohols
  6. Grignard Reaction in Organic Synthesis
  7. Protecting Groups For Alcohols
  8. Oxidation of Alcohols

Conjugated Systems

  1. Resonance and Conjugated Dienes
  2. Allylic Carbocations
  3. 1,2 and 1,4 Electrophilic Addition to Dienes
  4. Kinetic vs Thermodynamic Control of Electrophilic Addition to Dienes

The Diels-Alder Reaction

  1. Diels Alder Reaction: Dienes and Dienophiles
  2. Predict the Products of the Diels-Alder Reaction
  3. Endo and Exo products of Diels-Alder Reaction
  4. Regioselectivity of the Diels–Alder Reaction
  5. Identify the Diene and Dienophile of the Diels–Alder Reaction

Aromatic Compounds

  1. Naming Aromatic Compounds
  2. Introduction to Aromatic Compounds
  3. Aromaticity and Huckel's Rule
  4. What is the 4n+2 Rule?
  5. Identify Aromatic, Antiaromatic, or Nonaromatic Compounds

Electrophilic Aromatic Substitution

  1. Electrophilic Aromatic Substitution – The Mechanism
  2. Friedel-Crafts Alkylation
  3. Friedel-Crafts Acylation
  4. The Alkylation of Benzene by Acylation-Reduction
  5. Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution
  6. Limitations on Electrophilic Aromatic Substitution Reactions
  7. Orientation in Benzene Rings With More Than One Substituent
  8. Electrophilic Aromatic Substitution with Arenediazonium Salts

Aldehydes and Ketones

  1. Nomenclature of Aldehydes and Ketones
  2. Preparation of Aldehydes and Ketones
  3. Nucleophilic Addition to Carbonyl Groups
  4. The Addition-Elimination Mechanism
  5. Reduction of Carbonyl Compounds by Hydride Ion
  6. Reactions of Aldehydes and Ketones with Water
  7. Reactions of Aldehydes and Ketones with Alcohols: Acetals and Hemiacetals
  8. Acetals as Protecting Groups for Aldehydes and Ketones
  9. Reactions of Aldehydes and Ketones with Amines: Imines and Enamines
  10. Hydrolysis of Acetals, Imines and Enamines
  11. The Wittig Reaction: Alkenes From Carbonyls

Organic Synthesis Problems

  1. Multistep Organic Synthesis

Atoms, Molecules, and Ions

  1. Subatomic particles and Isotopes
  2. Atomic and Molecular Masses
  3. The Mole and Molar Mass
  4. Molar Calculations
  5. Percent Composition and Empirical Formula

Stoichiometry

  1. Molar Calculations in Chemical Equations
  2. Limiting Reactant
  3. Reaction/Percent Yield

Reactions in Aqueous Solutions

  1. Solutions: Strong and Weak Electrolytes
  2. Dissociation of Ionic Compounds
  3. Molarity and Percent Concentration
  4. Dilution
  5. Ion Concentration
  6. Precipitation Reactions
  7. Acid-Base Reactions
  8. Oxidation State
  9. Oxidation-Reduction (Redox) Reactions

Gases

  1. Ideal-Gas Laws
  2. Combined Gas Law Equation
  3. Molar Mass and Density of Gases
  4. Graham's Law of Effusion and Diffusion
  5. Dalton's Law of Partial Pressures
  6. Mole Fraction and Partial Pressure of the Gas
  7. Gases in Chemical Reactions

Thermochemistry

  1. Energy Related to Heat and Work
  2. Endothermic and Exothermic Processes
  3. Heat Capacity and Calorimetry
  4. State Functions and Enthalpy
  5. Stoichiometry and Enthalpy of Chemical Reactions
  6. Standard Enthalpies of Formation
  7. Hess's Law and Enthalpy of Reaction

Electronic Structure of Atoms

  1. Atomic Orbitals
  2. Electron Configurations

Concepts of Chemical Bonding

  1. Covalent and Ionic Bonds, Electronegativity, Bond Polarity, Partial Charges and Dipole Moments
  2. Lewis Structures and the Octet Rule
  3. Formal Charges and Resonance Structures

Molecular Geometry

  1. The VSEPR Model
  2. Hybridization of Atomic Orbitals

Intermolecular Forces in Liquids and Solids

Properties of Solutions

Chemical Kinetics

Chemical Equilibrium

Acid–Base Equilibria

Chemical Thermodynamics

Electrochemistry

Nuclear Chemistry