Chapter 11 Learning Objectives:

1. Be able to define:  oxidation, reduction, PCC, ether, alkoxide ion, carboxylic ester, tosylate ester, pinacol rearrangement.
2. Be able to predict the major product of a chromic acid or PCC oxidation of various alcohols.  Be able to draw the mechanism for each.
3. Know how to synthesize an tosylate ester from an alcohol.  Know the stereochemical outcome.  Be able to draw the mechanism.
4. Know the reactivity of a tosylate with a nuclephile.
5. Be able to predict the major product of the reaction of an alcohol with PX₃ (including stereochemistry) and draw the mechanism.
6. Be able to predict the major product of the reaction of an alcohol with SOCl₂ (including stereochemistry) and draw the mechanism.
7. Be able to predict the major product from the dehydration of an alcohol to form an alkene.  Be able to draw the mechanism.
8. Be able to draw the synthetic steps necessary to synthesize a target molecule from one or more given starting compounds.