Chemistry 2430 Quiz #6 - 10 points - Dr. Howard Black - Feb. 16, 1999 - Name         KEY

1. (6 pts total) Phenylpropanolamine, an anorexic present in virtually all OTC diet medications, can exist in several stereoisomeric forms. One of the active forms is illustrated below.
 

a. (1 pt) What is the significance - precisely - of the (+) in from of phenylpropanolamine under the upper structure? 

     it is dextrorotatory, i.e. it rotates light to the right

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

enantiomer       diastereomer      meso        same stereoisomer

Answer =         same stereoisomer      

c. (4 pts) What is the absolute configuration of each chiral center in each diagram above?

upper diagram: C-1:     S      C-2:     S          ||    Fischer projection: C-1:    S     C-2:    S

2. (4 pts) Complete the following reactions. If more than one product is produced, draw only the major one.