Professor Carl C. Wamser
1. Tell whether the compounds in each of the following pairs are non-isomeric, identical, constitutional isomers, enantiomers, or diastereomers. Also, assign configuration (R or S) to all stereocenters. Identify the optically active (chiral) compounds. Identify any meso compounds. Make molecular models of these compounds to confirm your assignments.
2. For each of the following reactions, predict whether the product will be optically active, a racemic mixture or achiral. Explain your choice.
a. (+)-2-chlorobutane ---(Br2 in CCl4, hv)---> 2-bromo-2-chlorobutane
b. (+)-2-chlorobutane ---(SO2Cl2 in CCl4, hv)---> 1,2-dichlorobutane
(Several other products are formed. This one is separated by gas chromatography.)
c. (+)-3-methylcyclopentene ---(H2, PtO2)---> methylcyclopentane
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