Organic Chemistry 1 - The Journey of a Thousand Steps

Organic Chemistry 1


General Outline

Organic Chemistry 1:

Atoms and Orbitals

Acids and Bases in Organic Chemistry

  • Introduction to Bonds and Molecules
  • Lewis Structures
    • Resonance Structures
  • Ways of Representing Molecules
    • Condensed Formula
    • Structural Formula
    • Bond-Angle Formula
  • Constitutional Isomerism
  • Formal Charge
formal charge vs charge density

Conformational Isomerism

IUPAC system of Nomenclature

  • Alkanes
  • Cycloalkanes
  • Alkenes
  • Alkynes
  • Alkyl Halides
  • Alcohols
  • Ethers
  • Other Functional Groups

Reactions of Alkenes: The Electrophilic Addition Reaction (AdE3)

alkene addition reactions
  • Reaction Coordinate Diagrams and the Potential Energy Surface
    • Transition States vs. Intermediates
    • Free Energy (G) & Enthalpy (H)
  • Carbenium ions/Carbocations
    • Hyperconjugation

Introduction to Mechanism: The Arrow-Pushing Formalism

electron movement
  • Regiochemistry
    • Markovnikov's Rule (Anti-Markovnikov Regiochemistry)

Relative Stereochemistry

  • Syn vs Anti Addition

Thermodynamics and Kinetics

  • Reactions of Dienes
  • Radical Reactions
    • Alkane Halogenation
    • Initiation, Propagation, Termination

Chirality and Stereochemistry

  • Configurational Isomerism
    • Cahn-Ingold-Prelog (C-I-P) Rules & Determination of Absolute Configuration
    • Enantiomers
    • Diastereomers
    • Meso Compounds
    • Optical Activity
    • Enantiomeric Excess
    • Racemic vs. Scalemic
  • Axial chirality, Helical chirality,
  • Prochirality and the Concepts of Homo- and Heterotopicity
  • Alkynes: Introduction to Synthesis—C-C bond formation
    • pKa of sp carbon and Acetylides
  • Addition Reactions of Alkynes

Reaction Pathways  at sp3 Carbons

  • (SN1/SN2)
    • Bimolecular and Unimolecular Substitution at sp3 Carbon.
    • Relative rates of reaction.

Important oxygen-containing functional groups, their synthesis and typical reactivity.

  • Alcohols, Ethers, and Epoxides
  • Pseudo Halides and Alcohol Activation
  • (E1/E2)
    • Bimolecular and unimolecular elimination mechanisms.
    • Zaitzev's Rule vs Hoffman's Rule.

Introduction to Retrosynthetic Analysis

  • Bond disconnection and planning

Structural Elucidation: Analysis and Identification of Organic Compounds

Mass Spectrometry (MS)

  • Electron Impact Mass Spectrometry
  • Molecular Ion peak vs. the Base Peak
  • Isotopes and their Consequences in MS

Infrared (IR) Spectroscopy

  • Hookes' Law
  • Absorption Spectroscopy
  • Bonds and their Stretch, Bend, and Wag Peaks.
  • Overtones and the Fingerprint Region.

lH and 13C Nuclear Magnetic Resonance Spectroscopy (NMR)

  • Nuclear Spin States
  • Free induction decay
  • Fourier transformation
  • Interpretation of NMR spectra

*Other Analytical Methods

(when taken with Organic Chemistry Laboratory)

UV-Vis spectroscopy

  • The Woodward Rules


  • [α°]D

Gas Chromatography

  • Retention Time

Thin-layer Chromatography

  • How can you tell when a reaction has gone to completion?

Column Chromatography

  • How do you purify side products from the desired product?

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