In clinical studies of patients with atherosclerosis (hardening of the arteries) it was

Chapter 21, Problem 21.38

(choose chapter or problem)

In clinical studies of patients with atherosclerosis (hardening of the arteries) it was found that one of the metabolites of the hyperlipidemia drug (Z)-3-methyl-4-phenyl-3- butenamide (A, in the reaction given in Fig. P21.38) is a compound B, which has the formula C11H15NO2. When compound B is heated in aqueous acid, lactone C is formed along with the ammonium ion (+NH4). (a) Propose a structure for compound B, and explain your reasoning. (b) Give a curved-arrow mechanism for the conversion of B into C

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