The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael addition) reaction as shown below: Ph OH OH Ph Warfarin a) Propose a mechanism for the reaction starting from the enolate shown below. You can assume water is present for any proton transfers needed. Ph :0: b) We saw that the keto tautomer is normally preferred over the enol tautomer, however, the enol tautomer is present in the final product (Warfarin) and that is the more stable tautomer in this case. Why do you think the enol tautomer is more stable? Hint: consider the molecule as a whole. Ph OH Ph O keto tautomer enol tautomer
The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael addition) reaction as shown below: Ph OH OH Ph Warfarin a) Propose a mechanism for the reaction starting from the enolate shown below. You can assume water is present for any proton transfers needed. Ph :0: b) We saw that the keto tautomer is normally preferred over the enol tautomer, however, the enol tautomer is present in the final product (Warfarin) and that is the more stable tautomer in this case. Why do you think the enol tautomer is more stable? Hint: consider the molecule as a whole. Ph OH Ph O keto tautomer enol tautomer
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
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.57P
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The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael addition) reaction as shown below:
a) Propose a mechanism for the reaction starting from the enolate shown below. You can assume water is present for any proton transfers needed.
b) We saw that the keto tautomer is normally preferred over the enol tautomer, however, the enol tautomer is present in the final product (Warfarin) and that is the more stable tautomer in this case. Why do you think the enol tautomer is more stable? Hint: consider the molecule as a whole.
Transcribed Image Text:The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael
addition) reaction as shown below:
Ph
OH
ОН Ph O
Warfarin
a) Propose a mechanism for the reaction starting from the enolate shown below. You can
assume water is present for any proton transfers needed.
Ph
:0:
b) We saw that the keto tautomer is normally preferred over the enol tautomer, however,
the enol tautomer is present in the final product (Warfarin) and that is the more stable
tautomer in this case. Why do you think the enol tautomer is more stable? Hint: consider
the molecule as a whole.
Ph
ОН Ph
keto tautomer
enol tautomer
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