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.

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

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.

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

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.

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

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.

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

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.

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

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.

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

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.