Organic Chemistry III

Professor Carl C. Wamser

Chapter 20 Workshop Problems

1. Provide structures that satisfy the following descriptions:

a. the structure of the compound, C8H10, that is converted upon vigorous oxidation with permanganate to a compound, C8H6O4, which loses water upon heating.

b. the structure of the compound, C6H10O3, that exhibits strong absorption in the infrared spectrum at 1754 cm-1 and 1818 cm-1 and the following 1-H NMR spectrum:
1.19 ppm (t, rel. area 3, J = 7.0 Hz) and 2.48 ppm (q, rel. area 2, J = 7.0 Hz).

c. the stereoisomer of 3-hydroxycyclohexanecarboxylic acid that is capable of forming a lactone.

d. the structure of the compound, C6H12O2, that would undergo reaction with excess ethyl magnesium bromide to give the compound shown below.

2. Propose a plausible mechanism for each of the following reactions. Provide all important Lewis structures that contribute to the resonance hybrid for delocalized intermediates, and point out any important driving forces.

3. Give the structure(s) of the major organic product(s) for the following reactions.

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