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.
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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.
