(a) Explain why the following substituted acetic acid cannot be formed by the malonic ester synthesis.

(b) Sections 22-2B and 22-3 showed the use of lithium diisopropylamide (LDA) to deprotonate a ketone quantitatively. Draw the acid-base reaction between LDA and the following ester, and use estimated pKa values to decide whether the reaction favors the reactants or products at equilibrium.

(c) Show how you might use a modern alternative to the malonic ester synthesis to make the acid shown in part (a). You may use the ester shown in part (b) as your starting material.

CH3 H,C-C-C CH3 OH CH3 CHCOCH3