Stereochemistry Part 2 Solutions: #14

14.* (1994 1 6) Two structures for thalidmoide are shown below.

A. Which of the following terms describe these substances:
diastereomisomers, enantiomers, mesoisomers, identical, optically active.

Enantiomers and optically active.

B. Designate each of these compounds as R or S.

 

C. How many sites of unsaturation are found in thalidomide? Identify these.

10 sites of unsaturation: 3 alkene groups ( C=C )

4 carbonyls ( C=O )

3 rings

D. Are there any aromatic groups in thalidomide? Explain.

The six-membered ring with alternating pi bonds is aromatic

-continuous cycle of oriented p orbitals

-6 pi electrons

The other rings in the structure are not aromatic.