Chem 336 - Spring 1999 - Organic Chemistry III
Portland State University - Dr. Carl C. Wamser
Chapter 22 Skills
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
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
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
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
use Diels-Alder, Cope, and Claisen reactions as part of a synthetic sequence