Qu. 3. A graduate student, Mr. I. M. Moleculeski, was having a hard time alkylating ketone A at the more substituted a-carbon to give needed B: the products were c1 & C2. Remarkably, changing the reactant to D smoothly gave E! Show the mechanism for formation of E and the stereochemical outcome at the a- center, and explain the formation of E, C1 & 02. Hint: make a model (10 pt) 1 equiv. Br NaH B C1 C2 1 equiv. Br NaH RO RO E F MeOOC COOME WAG