General, Organic, and Biological Chemistry
7th Edition
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:H. Stephen Stoker
Chapter18: Carbohydrates
Section: Chapter Questions
Problem 18.30EP
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Question
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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F080ba3bb-16f3-4634-88f0-353189793abc%2F0b32dd35-f004-4c59-85e9-2c2d371a9ae1%2Fcmnwx9d.png&w=3840&q=75)
Transcribed Image Text:НА
HO
HO
R isomer
inactive enantiomer
S isomer
active enantiomer
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