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
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...
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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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