Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter 2005	Chapter 16 Quiz

1. (3 points) An ether of formula C5H12O was made by a Williamson ether synthesis and its structure was confirmed by NMR because it showed only two singlets, areas 9 and 3. Identify the ether and the reaction most likely to have been used to synthesize it.

2. (3 points) Complete each of the following reactions by adding the expected major product. Show stereochemistry if it is specific.

a)

b)

c)

3. (4 points) Write a complete mechanism for the cleavage of t-butyl methyl ether using HI. Show all steps and electron-pushing arrows. You may cleave the two parts in either order.