Thalidomide is a chiral molecule and it was identified that the R-isomer produced the sedative properties whereas the S-isomer produced the teratogenic effects. Identify the chiral centre in the thalidomide molecule and, using your knowledge of enolisation, illustrate mechanistically, and explain, why there would be no benefit to a patient taking the chirally pure R-isomer of the drug to avoid the sideeffects of the other enantiomer.

Thalidomide is a chiral molecule and it was identified that the R-isomer produced the sedative properties whereas the S-isomer produced the teratogenic effects. Identify the chiral centre in the thalidomide molecule and, using your knowledge of enolisation, illustrate mechanistically, and explain, why there would be no benefit to a patient taking the chirally pure R-isomer of the drug to avoid the sideeffects of the other enantiomer.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.53P

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