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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?

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    $\begingroup$ Your analysis shows some correct lines of reasoning, but the overall reasoning is unclear. The way to solve the problem is to look at the two structures that could be created from reaction at the two respective nucleophilic sites. More importantly, do not confuse basicity in general with nucleophilicity. Those are separate concepts, and you can find examples of non-basic nucleophiles and non-nucleophilic bases. $\endgroup$ – Zhe Jan 12 at 18:04

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