Chem 334 - Summer 1998 - Organic Chemistry I Dr. Carl C. Wamser

Chapter 9 Homework - Alcohols. Reactions

Vollhardt & Schore, pp 315 - 323
Problems 1 , 2 , 3 , 4 , 9 , 10 , 11 , 12 , 14 , 15 , 19 , 21 , 22 , 24 , 26 , 29

1. Balance each of the following redox reactions:

3-octanol + KMnO4 (basic solution)

1-octanol + Na2Cr2O7 (acidic solution)

cyclohexene + KMnO4 (hot, acidic solution)

2. Ethers left open to the air for extended periods can become explosive due to the formation of hydroperoxides. Write a free radical chain mechanism for the air oxidation (autoxidation) of diethyl ether, initiated by an arbitrary radical R. .

3. Write two complete mechanisms for the addition of ethanol to 1-methylcyclohexene oxide:

a) catalyzed by acid (HCl in ethanol)

b) catalyzed by base (NaOEt in ethanol)