Organic Chemistry 1

 

General Outline

Organic Chemistry 1:

Atoms and Orbitals

• Atomic and Molecular Orbitals
• Basic Quantum Chemistry and Electron Configuration

• Trends in the Periodic Table
  • Electronegativity
  • Atomic Radius/Polarizability

Acids and Bases in Organic Chemistry

• Definitions
• pKa
• Inductive Effects
• Resonance Effects

• Introduction to Bonds and Molecules
  • Hybridization
  • Types of Bonds

• Lewis Structures
  • Resonance Structures

• Ways of Representing Molecules
  • Condensed Formula
  • Structural Formula
  • Bond-Angle Formula

• Constitutional Isomerism

• Special Topic: The Molecular Model Kit

• Formal Charge

Conformational Isomerism

• Other Representations
  • Newman Projections
  • Cyclohexane Conformers
  • Fischer Projections

IUPAC system of Nomenclature

• Alkanes
• Cycloalkanes
• Alkenes
• Alkynes
• Alkyl Halides
• Alcohols
• Ethers

• Other Functional Groups

Reactions of Alkenes: The Electrophilic Addition Reaction (Ad_E3)

• 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

• 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

• (S_N1/S_N2)
  • 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

Polarimetry

• [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?