Esters are normally unreactive toward sodium borohydride, but they react readily with lithium aluminum hydride to produce alcohols.
a. Propose a rationale for the lack of reactivity of esters toward NaBH4
b. Propose a rationale for the greater reactivity of lithium aluminum hydride over that of sodium borohydride.
c. Write the structures of the organic products that will be formed when methyl benzoate is treated with lithium aluminum hydride and the reaction mixture is worked up with aqueous acid.