Chem 335 - Winter 2000
Organic Chemistry II
Dr. Carl C. Wamser

Challenge Problem

Challenge problem: group work (3 - 4 people)

Hydrolysis of t-butyl acetate can be carried out with either acid or base.

a) In O-18 enriched water, what product or products would be expected to contain O-18 ?

b) In fact, O-18 shows up in different places, dependingon whether acid or base is used. Explain.

c) With acid catalysis, isobutylene (2-methylpropene)is a significant product.
Where does it come from? Why isn't this seen in base?