qwerty123qw

I cant seem to figure this out. If a benzene ring has 2 substituents 1) OH group 2) COOH group and we are attacking the electrophile carbon in the carbonyl CH3C=OOC=OCH3 (acet. anhydride), why is the O from OH rather than the O from the OH in COOH used? Both cant go through resonance, so what other differences would there be.

Wait starpaste i think you mean in RCOOH? if it is HO--C=O, i thought it would be the OH bc it is more basic than c==o. yet it the O in c=o is still the better nucleophile?