This drug’s single stereocenter can undergo chiral inversion at a nitrogen–carbon bond. For 10 points each:
[10e] Name this drug that was used to treat morning sickness that caused birth defects. The two isomers of this drug interconvert, although only the S isomer is biologically active.
ANSWER: thalidomide [or Contergan; or Thalidomid]
[10m] Thalidomide does not possess these isomers, which have more than one stereocenter, but remain superimposable. For two stereocenters, these optically inactive compounds have (R,S) (“R S”) configuration.
ANSWER: meso compounds
[10h] This form of spectroscopy uses the difference in absorption of polarized light. A vibrational form of this technique operates in the infrared, while a UV form can probe the secondary structure of proteins.
ANSWER: circular dichroism [or CD]
<Oxford B, Chemistry>