One piece of evidence supporting the enol mechanism in Eq. 20.39 is that b-keto acids that cannot

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One piece of evidence supporting the enol mechanism in Eq. 20.39 is that βb-keto acids that cannot form enols are stable to decarboxylation. For example, the following b-keto acid can be distilled at 310°C without decomposition. Attempt to construct a model of the enol that would be formed when this compound decarboxylates. Use your model to explain why this b-keto acid resists decarboxylation.COH

H3C BC. CH acetoacetic acid (a -ketoacid) OH H3O+ 25 C H3C CH3 acetone + CO (20.39a)

H3C H gy H OH MA HC CH acetone enol (Sec. 14.5A) H3C CH3 acetone (20.39b)

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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