General Principles

Other Topics

• Mass Spectrometry
• Ultraviolet-Visible Spectroscopy
• Infrared Spectroscopy
• Nuclear Magnetic Resonance Spectroscopy

• Principles of Modern Synthesis
• Stereoselective Synthesis

Functional Group Reactions

Alkanes

• Combustion
• Halogenation of Alkanes

Alkenes

• Addition Reactions
  • Addition of Strong Bronsted Acids
  • Addition of Lewis Acids (Electrophilic Reagents)
  • Rearrangement of Carbocations
• Stereoselectivity in Addition Reactions to Double Bonds
  • Addition Reactions Initiated by Electrophilic Halogen
  • Addition Reactions involving other Cyclic Onium Intermediates
  • Brønsted Acid Additions
  • Hydrogenation of Alkenes
  • Oxidations
    • Epoxidation
    • Hydroxylation
    • Oxidative Cleavage of Double Bonds
• Free Radical Reactions of Alkanes
  • Addition of Radicals to Alkenes
  • Allylic Substitution
• Dienes
  • Addition Reactions
  • Diels-Alder Cycloaddition

Alkynes

• Addition Reactions
  • Addition Reactions by Elecrophilic Reagents
  • Catalytic Hydrogenation
  • Hydration & Tautomerism
  • Hydroboration
• Nucleophilic Addition & Reduction
• Acidity of Terminal Alkynes

Alkyl Halides

• Alkyl Halide Occurrence
• General Reactivity
  • Reactions with Reducing Metals
  • Reactions of Dihalides
  • Substitution and Elimination Reactions
    • E₁ Elimination
    • E₂ Elimination
      • Planar Configuration & Bredt's Rule
      • Stereochemistry of E₂ reactions
    • SN₁ Substitution
      • Molecularity & Kinetics
      • Nucleophilicity & Solvent Effects
      • Steric Hindrance to Rear-side Approach
    • SN₂ Substitutions & Alkyl Moiety

Alcohols

• Alcohol Nomenclature
• Electrophilic Substitution at Oxygen
• Elimination Reactions
• Hydroxyl Groups
• Phenols
  • Acidity of Phenols
  • Ring Substitution of Phenols
  • Oxidation to Quinones

Ethers

• Nomenclature
• Ether Synthesis
• Reactions of Ethers
• Epoxide Reactions

Thiols & Sulfides

• Sulfur Analogs of Alcohols & Ethers

Benzene & Derivatives

• Electrophilic Aromatic Substitution
• Characteristics of Specific Substitution Reactions of Benzenes
• Substitution Reactions of Benzene Derivatives
• Nucleophilic Reactions of Benzene Derivatives
• Reactions of Substituent Groups
• Reactions of Fused Benzene Rings
• Electrophilic Substitution of Di-substituted Benze Rings

Amines

• Nomenclature & Structure
  • Natural Nitrogen Compounds
• Properties of Amines
• Preparation of Amines
• Amine Reactivity
• Oxidation States of Nitrogen
• Substitution and Elimination Reactions of Amines
• Reactions with Nitrous Acid
• Reactions of Aryl Diazonium Intermediates

Phosphines

• Phosphorus Analogs of Amines

Aldehydes & Ketones

• Nomenclature of Aldehydes & Ketones
• Occurrence of Aldehydes & Ketones
• Properties of Aldehydes & Ketones
• Reactions 
  • alpha-carbon Reactions
  • Carbonyl Group Reactions
  • Irreversible Addition Reactions
  • Reversible Addition Reactions

Carboxylic Acids

• Nomenclature of Carboxylic Acids
• Natural Products
• Related Derivatives
• Physical Properties
  • Acidity
• Preparation of Carboxylic Acids
• Reactions of Carboxylic Acids
  • Salt Formation
  • Substitution of Hydroxyl Hydrogen
  • Substitution of the Hydroxyl Group
  • Reduction & Oxidation
    • Practice Problems

Carboxylic Derivatives

• Physical Properties
• Nomenclature
• Reactions of Carboxylic Acid Derivatives
  • Acyl Group Substitution
    • Mechanism
  • Reduction
    • Catalytic Reduction
    • Metal Hydride Reduction
    • Diborane Reduction
  • Reaction with Organometallic Reagents
    • Practice Problems
• Reactions at the α Carbon
  • Acidity of α C–H
  • The Claisen Condensation
• Synthesis Applications
  • Practice Problems