Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter 2008	Quiz 10

1.  (2 points)  Write a complete mechanism for the addition of one equivalent of HI to the diene below.  Show all resonance forms and indicate whether the products are the result of 1,2 or 1,4 addition.

2.  (3 points)  Complete the synthetic sequence below by filling in the missing boxes.

3.  (5 points)  The compound below undergoes SN1 hydrolysis to form three possible alcohols.  Show the resonance forms for the intermediate and the structures of the expected three products.

Which resonance form is expected to make the major contribution?  (Circle it)
Which product is expected to be most stable?  (Circle it)
Which product is most likely to be the product of kinetic control?  (label it KC)
Which product is most likely to be the product of thermodynamic control?  (label it TC)