Although one enantiomer of the drug thalidomide is a sedative, the other is teratogenic (causes birth defects). Unfortunately, thalidomide is racemized in the body and, for that reason, both enantiomers are teratogenic. (See Fig.) Assuming the availability of acids and bases as needed, give a curved-arrow mechanism for the base-catalyzed racemization of thalidomide in water.

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N O (S)-thalidomide Figure P22.72 H FO (R)-thalidomide H