Enols, like phenols, have pK a values of ~1011. However, the pK a of warfarin, a widely

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Enols, like phenols, have pKa values of ~10–11. However, the pKa of warfarin, a widely used anticoagulant, is 5.0.0 CH- CH CH3 warfarin (Coumadin)

(a) Give the structure of the conjugate base of warfarin.

(b) Use resonance arguments to justify the unusually low pKa of warfarin.

(c) What is the predominant form of warfarin—enol or conjugate base—at physiological pH (7.4)?

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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