addition) reaction as shown below: me OH ÓH 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:

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Chapter1: Chemical Foundations
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6. The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael
addition) reaction as shown below:
Ph
ОН
ОН 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
ОН Ph
keto tautomer
enol tautomer
5
Transcribed Image Text:6. The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael addition) reaction as shown below: Ph ОН ОН 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 ОН Ph keto tautomer enol tautomer 5
4. The following enolate alkylation reaction is attempted in the laboratory as shown:
1. NaOH
2. CH3BR
desired product
The 'H NMR shown below was taken after the reaction.
6H
3H
2H
1H
6.
4
3
1
PPM
a) Does the NMR shown above match the desired product? How could
you
tell?
b) Use a mechanism to show how the product that matches the NMR above is formed
under the given conditions.
c) Suggest an alternate (or better) way to perform the reaction to obtain the desired
product above. Be sure to give a specific example of the conditions.
Transcribed Image Text:4. The following enolate alkylation reaction is attempted in the laboratory as shown: 1. NaOH 2. CH3BR desired product The 'H NMR shown below was taken after the reaction. 6H 3H 2H 1H 6. 4 3 1 PPM a) Does the NMR shown above match the desired product? How could you tell? b) Use a mechanism to show how the product that matches the NMR above is formed under the given conditions. c) Suggest an alternate (or better) way to perform the reaction to obtain the desired product above. Be sure to give a specific example of the conditions.
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