1. Organic Chemistry, 6 th edition Paula Yurkanis Bruice Chapter 10 Reactions of Alcohols, Amines, Ethers, Epoxides, and Sulfur- Containing Compounds Brian L. Groh Minnesota State University, Mankato Mankato, MN Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

2. Which alkene is the major product of this dehydration? 10.4 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

3. Which alkene is the major product of this dehydration? 10.4 Acid catalyzed dehydration generally gives the most stable alkene. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

4. Which alkene is the major product of this dehydration? 10.4 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

5. Which alkene is the major product of this dehydration? 10.4 S N conditions favor rearrangement of the carbocation intermediate. Only small amounts of A and B will form. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

6. Which alcohol will not be oxidized by chromic acid? 10.5 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

7. Which alcohol will not be oxidized by chromic acid? 10.5 Tertiary alcohols will not be oxidized with chromic acid. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

8. What is the major product of this reaction? 10.6 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

9. What is the major product of this reaction? 10.6 Protonation of the oxygen will be followed by nucleophilic attack by I - at the least hindered carbon. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

10. What is the major product of this reaction? 10.7 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

11. What is the major product of this reaction? 10.7 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. Under acidic conditions the alcohol attacks the more electrophilic tertiary carbon of the protonated epoxide.

12. What is the major product of the following reaction? 10.9 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

13. What is the major product of the following reaction? 10.9 This is the Hoffman elimination which favors formation of the least substituted alkene. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.