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

Chapter 11 Homework Answers

Brown & Foote, pages 426 - 433:
Problems 11.10 - 22 , 26 - 30 , 35 - 38

1. Give complete names for each of the following:

a)

4,4-dimethoxycyclopentene

b)

(Z)-4-propoxyhex-4-en-1-ol

2. Write a complete mechanism for the conversion of 1-pentanol to tert-butyl pentyl ether (a protection reaction). Also show the complete mechanism for the deprotection reaction (tert-butyl pentyl ether to 1-pentanol) using dilute aqueous acid.

3. Write a complete mechanism for the addition of methanol to 1-methylcyclohexene oxide, using acid catalysis (H2SO4) and using base catalysis (NaOCH3).