COURSE CONTENT

ORGANIC CHEMISTRY I

CHE 230 - C781

  1. CARBON COMPOUNDS AND CHEMICAL BONDS
    1. Introduction to Organic Chemistry
    2. Types of Bonds
      1. Ionic
      2. Covalent
      3. Polar Covalent
    3. Chemical Bonds
      1. Lewis Structure
      2. VSEPR Repulsion Theory
      3. Valence Bond (Atomic Orbits) Theory
            a. sp3 Hybridization
            b. sp3 Hybridization
            c. sp3 Hybridization
    4. Structural Formulas
      1. Dash Formula
      2. condensed Dash Formula
      3. Bond Line Formulas

II. CARBON COMPOUNDS

    1. Classes of Carbon Compounds
      1. Alkanes
            a. Single Bond
            b. sp2 Hybridization
            c. Examples + Geometry
      2. Alkenes
            a. Double Bond
            b. sp2 Hybridization
            c. Examples + Geometry
      3. Alkynes
            a. Triple Bond
            b. sp Hybridization
            c. Examples + Geometry
    2. Functional Groups
      1. Definitions
            a. Functional Group
            b. Alkyl Group (R)
      2. Alkyl Halides
      3. Alcohols
      4. Ethers
      5. Amines
      6. Aldehydes
      7. Ketones
      8. Esters
      9. Carboxylic Acids
    3. Physical Properties/Molecular Structure
      1. Ion-Ion forces
            a. Melting point
            b. Boiling point
      2. Dipole-dipole forces
            a. Hydrogen bond
      3. London, Dispersion or
      van der Waals Forces
      4. Solubility

III. ACIDS AND BASES IN ORGANIC CHEMISTRY

    1. Reaction Categories
      1. Substitution
      2. Addition
      3. Elimination
      4. Rearrangement
    2. Bond Cleavage
      1. Heterolysis
      2. Homolysis
    3. Definition of Acids and Bases
      1. Brønsted-Lowry Theory
      2. Lewis Theory
            a. Electrophiles
            b. Nucleophiles
    4. Mechanisms
      1. Purpose
      2. Intermediates
      3. Use of curved arrows
    5. Acid and Base Strength
      1. pH
      2. Effect of Structure
      3. Effect of Equilibrium Constant
      4. Effect of ∆Gš, Standard Free Energy Change
      5. Effect of Solvent

IV. ALKANES AND CYCLO ALKANES

    1. Introduction
    2. Sources
      1. Petroleum Cracking
      2. Petroleum Refining
    3. Physical Constants
    4. Nomenclature
      1. Non-branched Compounds
      2. Branched Compounds
    5. Bond Rotation
      1. Staggered form
      2. Eclipsed form
    6. Conformational Analysis
      1. Ring Strain
      2. Angle Strain
      3. Torsion Strain
    7. Cyclohexane
      1. Chair Form
      2. Boat Form
    8. Synthesis of Alkanes & Cycloalkanes

V. STEREOCHEMISTRY: CHIRAL VS. ACHIRAL MOLECULES

    1. Isomers
      1. Constitutional Isomers
      2. Stereoisomers
            a. Enantiomers
            b. Diastereomers
      3. Chirality/Mirror Images - Handed-ness
            a. Achiral - Superimposable
            b. Chiral - Non superimposable
            c. Importance
            d. Historical Importance
            e. Plane of Symmetry
    2. Enantiomers
      1. Nomenclature - The (R-S) System
      2. Properties: Optical Activity
      3. Effect of Plane-Polarized light
    3. Optical Activity
      1. Origin
      2. Racemic form
    4. Synthesis of Enantiomers
      1. Racemic form
      2. Enantioselective
    5. Chiral Drugs
      1. Examples
      2. Importance
    6. Molecule with more than one Stereocenter
      1. Possible isomers 2n
      2. Meso Compounds
      3. Cyclic Compounds
    7. Resolution - Separation of Enantiomers
      1. Definition
      2. History
      3. Importance

VI. IONIC REACTIONS - NUCLEOPHILIC SUBSTITUTION AND ELIMINATION REACTIONS

    1. Organic Halides
      1. Introduction
      2. Physical Properties
    2. Nucleophilic Substitution
      1. General Type
      2. Parts
            a. Nucleophile
            b. Leaving Group
            c. Rate Control
      3. SN2 Reaction
            a. Mechanism
            b. Free Energy Change
            c. Stereochemistry
      4. SN1 Reaction
            a. Mechanism
            b. Free Energy Change
            c. Stereochemistry
      5. Determining Factors
            a. SN2 vs SN1
            b. Structure of Substrate
            c. Solvent Effects
            d. Nature of Leaving Groups

 

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