Below is one way of organizing the topics of organic chemistry into internally consistent groups.

I. Topics from general chemistry
II. Nomenclature
III. Emphasis on electron effects
IV. Chiral centers and optical activity
V. Means of deducing structure
VI. Reaction mechanism
VII. Reagents and Products
VIII. Biomolecules

First semester of a standard class tends to focus on the first four or five, with nomenclature being the most often revisited (at intervals). Reactions are first explored usually towards the end of first semester, starting with SN2, SN1, E2, and E1, as well as radical halogenation, then moving to reactions of alkenes.

Second semester often vastly expands the reactions repertoire. (This means there will be a whole lot of reactions!) The course usually ends with some kind of rough translation of organic chemistry to the level of proteins, fatty acids, and nucleic acids.


Stuart Han - Organic Chemistry Tutor - 773 392 3823

I. Topics from General Chemistry

    A. Assembly of atoms into molecules
      1. periodic trends
      2. electronegativity
      3. lewis structures
      4. formal charge
      5. dipole moment
      6. geometry
      7. hybridization
    B. Reacting molecules
      1. energy level diagrams
      2. kinetics/thermodynamics
      3. acids and bases
      4. oxidation and reduction

II. Nomenclature: vocabulary and grammar

    A. simple aliphatics and the longest chain
    B. cycloalkanes
    C. functional groups
    D. substituent names and positions
    E. weird names

III. Electron Effects: s v. p

    A. new stories on hybridization
      1. bonding, anti-bonding, and non-bonding
      2. lobes and positioning
    B. induction
    C. resonance
    D. aromaticity

IV. Chiral Centers and Optical Activity

    A. basic criteria for chiral centers
    B. cahn-ingold-prelog
    C. stereochemistry
      1. R v. S
      2. rules of paper
    D. optical activity
      1. plane polarized light
      2. dextrorotatory and levorotatory
    E. cancellation of optical activity
      1. enantiomers in racemic mixtures v. meso compounds
      2. symmetry elements
    F. multiple chiral centers: diastereomers and a few enantiomers
    G. calculations (e.g. enantiomeric excess)

V. Structural Games

    A. IR
    B. mass spec
    C. NMR

VI. Reactions

    SN and E
    radical halogenation of alkanes
    alcohols; thiols; ethers/epoxides
    polyenes and cycloaddition
    carboxylic acids and acid derivatives
    amines; amides; nitriles
    a-substitution; Michael addition (to a,b-unsaturated carbonyl compounds)
    biomolecules (a-amino acids, polyols)


Stuart Han
Private Tutor
Organic Chemistry Specialist
Evanston, IL
Northwestern University