In the the compound RCONH2 which lone pair is more basic? Is it the lone pairs on Oxygen atom or the lone pair on Nitrogen atom.
I believe that as O is more electronegative than N, the lone pair on O is of lower energy. Hence, the O's lone pairs are less basic. (But if one draws the resonance structure for the compound, a formal negative charge is found on the oxygen atom and the Nitrogen lone pairs are engaged in making bond)
So which atom should react first with an neutral electrophile?