The question is all about the sequence of a possible Birch- and Bouvault-Blanc-Reduction in this exemplary substrate. With which reduction the mechanism begin?
My first attempt was to classify the aromatic system as a nucleophilic center, whereas the ester group as an electrophilic center. But as which should the solvated, "free" electron be classified? Maybe, because of its charge, simple as a nucleophilic reagent, which therefore first attacks the nucleophilic aromatic ring? Is this simple explanation right? Because in the Bouvault-Blanc reduction the attack also takes places on the nucleophile, partial negatively charged O-Atom.
This question was inspired by the II,5th Supplementary problem of the book "The Art of Problem solving in Organic Chemistry" (Alonso-Amelot, Second edition). There, the Birch reduction takes place first, but the author delivers (for me) no neat explanation.