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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.
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
alkenes
alkynes
organometallics
reduction
oxidation
alcohols; thiols; ethers/epoxides
polyenes and cycloaddition
arenes
aldehydes/ketones
carboxylic acids and acid derivatives
amines; amides; nitriles
a-substitution; Michael addition (to a,b-unsaturated carbonyl compounds)
biomolecules (a-amino acids, polyols)
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Stuart Han
Private Tutor
Organic Chemistry Specialist
Chicago (Rogers Park), IL - Evanston, IL
Loyola University - Northwestern University
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