Chemistry 332 - Spring 1996
Elements of Organic Chemistry II

Homework, Chapter 9 - Carbonyl Compounds


McMurry, pp 281 - 284:
Problems 9.20, 22-24, 26-32, 34-40, 44, 47


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 (H2O18) slowly becomes radioactive itself.