Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2004

Chapter 10 Quiz

Conjugation

1. (4 points) Complete each of the following reactions by adding the missing part: either the starting compound, the necessary reagents and conditions, or the final major product. Show stereochemistry if it is specific.

a)

b)


2. (2 points) Write an approximate picture of the HOMO of 1,3-butadiene. Just illustrate the p orbitals and their symmetry.


3. (4 points) Allylic bromination of 1,2-dimethylcyclohexene by NBS gives four possible products (not counting stereoisomers). Write out all the resonance forms for the possible radical intermediates and show the structures of the products they lead to. (A complete mechanism is not required.)