Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2006

Chapter 17 Homework

Carey, pages 772 - 781 :
Problems 17.22 - 50


1. Write complete names for each of the following:

a)

b)

2. Write a complete mechanism for the acid-catalyzed formation of the cyclic acetal between acetone and cis-1,2-cyclopentanediol.
Explain why an acetal is not formed with the trans isomer.

3. Develop a synthetic sequence for 3-ethyl-3-hexanol that uses as organic starting materials only alcohols having four carbons or fewer.

4. Explain how acetone in the presence of radioactively-labelled water (H2O-18) slowly becomes radioactive itself.