НА HO HO R isomer inactive enantiomer S isomer active enantiomer

Organic And Biological Chemistry
7th Edition
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:STOKER, H. Stephen (howard Stephen)
Chapter7: Carbohydrates
Section: Chapter Questions
Problem 7.30EP
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Although ibuprofen is sold as a racemic mixture, only the S enantiomer acts as an analgesic. In the body, however, some of the R enantiomer is converted to the S isomer by tautomerization to an enol and then protonation to regenerate the carbonyl compound. Write a stepwise mechanism for this isomerization.

НА
HO
HO
R isomer
inactive enantiomer
S isomer
active enantiomer
Transcribed Image Text:НА HO HO R isomer inactive enantiomer S isomer active enantiomer
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