Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2006

Chapter 10 Homework

Carey, pages 439 - 445 :
Problems 10.19 - 42


1. Write all the possible stereoisomers that could result from the Diels-Alder reaction of (E,E)-2,4-hexadiene with cis-2-butenedinitrile (cis-1,2-dicyanoethylene).

Given the preference for endo addition and minimizing steric hindrance, predict the major product(s). Would this product be described as racemic, achiral, or optically active?