Chemistry Workshops

for Organic Chemistry

Workshop 14
Conjugation and Diels-Alder Reactions


1. Draw all of the important resonance structures for each of the structures below. Clearly indicate all of the non-zero atomic charges for all the structures. Indicate which of the resonance structures are more or less important.

2. Draw the four pi molecular orbitals (MOs) for 1,3-butadiene. Show how the energies of each of these MOs would be affected by including a 1,4 interaction as shown below.

3. Give the products of the following reactions:

4. Give the reagents and products as appropriate for the following synthetic sequences:

5. Specify the reagents, reactants and conditions you would use to carry out the following synthetic sequence.


Materials adapted from:

Peer-Led Team Learning: Organic Chemistry, 1/e
Jack A. Kampmeier, University of Rochester
Pratibha Varma-Nelson, St. Xavier University
Donald Wedegaertner, University of the Pacific
Prentice-Hall, 2001, ISBN 0-13-028413-0

http://www.sci.ccny.cuny.edu/~chemwksp/OrganicChem.html