Ch242/335  Organic Chemistry II  Winter 2005

Performance Objectives

Chapter 9

By the completion of chapter 9, students will:

1 .give correct names for structures, and provide structures when given names, for alcohols and thiols.

2.  compare the physical properties of alcohols and thiols with like alkanes and alkenes, and explain these properties by applying understanding of alcohol and thiol structure.

3.  describe the acidity and basicity of alcohols and thiols and make reasonable predictions about pKa values for these compounds.

4.  write reactions for alcohols and active metals.

5.  write reactions for substitution reactions of alcohols, including reaction with hydrogen halides, PBr₃, and thionyl chloride.

6.  write reactions describing the acid-catalyzed dehydration of alcohols.

7.  write reactions of the pinacol rearrangement.

8.  write reactions describing the oxidation of alcohols to aldehydes, ketones, and carboxylic acids, and the oxidative cleavage of diols.

9.  write reactions describing the oxidation of thiols to form disulfides and describe the importance of such reactions in biochemistry.

Suggested homework problems for chapter 9:  14, 15a-g, 16a-f, 18, 22, 27a-c, 29a and b, 32, 33, 36a-c.