Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter Term	Quiz 10

1. (2 points) Write the expected product for the following reaction:

a)

b)

2. (2 points) Draw clear pictures that show the orbital symmetry of the following molecular orbitals.

a) the HOMO for 1,3,5-hexatriene

b) the LUMO for the allyl cation

3. (2 points) SN1 hydrolysis of the allylic bromide shown below gives two alcohol products.
Show both allylic resonance forms and the structures of the two expected products.
Predict the more stable product.

4. (4 points) Addition of HBr to the diene below (both 1,2- and 1,4-additions) gives a total of four products.
Show the two allylic cations (with both resonance forms for each) and the four possible products.
Identify each product as either a 1,2 or 1,4 addition.