Chem 336 - Spring 2000
Organic Chemistry III

Dr. Carl C. Wamser


Chapter 22 Skills


Knowledge - Level 1

know the terminology:

molecular orbitals, bonding/nonbonding/antibonding, HOMO, LUMO
conjugate addition, 1,2- vs 1,4-addition
kinetic control vs. thermodynamic control
cycloaddition, pericyclic reaction, aromatic transition state
Diels-Alder reaction, Cope rearrangement, Claisen rearrangement
s-cis and s-trans
dienophile, exo vs. endo


Concepts - Level 2

identify conjugated pi systems, the number of pi MOs, and the number of pi electrons

explain the significance of kinetic or thermodynamic control of a reaction in terms of a reaction mechanism and an energy diagram

identify a pericyclic transition state, including the number of electrons involved


Applications - Level 3

write MOs for a conjugated pi system, including the pattern of energy levels and electron populations

write conjugate addition products for conjugated pi systems

predict the products from a Diels-Alder, Cope, or Claisen reaction


Analytical Skills - Level 4

write reaction mechanisms for conjugate addition, including alternative pathways and predictions of preferred pathways

write electron-pushing arrows and/or MO interaction pictures to illustrate reaction mechanisms of pericyclic reactions

predict preferred stereochemistry in pericyclic reactions


Synthesis Skills - Level 5

use Diels-Alder, Cope, and Claisen reactions as part of a synthetic sequence