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
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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.
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