Name______KEY____________________

1. (6 pts total) Phenylpropanolamine (PPA) is an anorexic that is the active ingredient in virtually all OTC diet medications. The most pharmacologically active stereoisomer is depicted below.
 

a. (1 pt) What is the significance of the (-) in front of phenylpropanolamine under the structure? __levorotatory - rotates plane-polarized light counterclockwise______

b. (1 pt) A Fischer projection of the same compound (but not necessarily the same stereoisomer) is drawn to the left (Ph means phenyl, which is the six-membered ring in the upper diagram). Which of the four terms underlined below describe its stereochemical relationship to the first (-) isomer depicted above it (write the correct answer on the line)? enantiomer     diastereomer     meso     same compound

c. (4 pts) What is the absolute configuration (i.e., R/S) of each chiral center in each diagram above?

upper diagram: C-1: __R__ C-2: __S___ Fischer projection: C-1: __S___ C-2: __R___

3. (4 pts) Complete the following reactions. If more than one product is formed, draw only the major one.