Starting from a Lewis diagram of in which the left oxygen bears a single bond to…

CHEMISTRY · Single correct · A Level · Chemistry · Introduction to organic chemistry · Introduction to organic chemistry

Problem

Starting from a Lewis diagram of NO2−\text{NO}_2^{-} in which the left oxygen bears a single bond to nitrogen and a negative formal charge, which of the following curved-arrow descriptions correctly generates the alternative resonance contributor where the left oxygen is double-bonded to nitrogen and the negative charge resides on the right oxygen? (a) Move one lone pair from nitrogen into the N–O single bond while shifting the N=O π\pi electrons onto the right O as a lone pair. (b) Move one lone pair from the right O into the N–O bond while pushing the N=O π\pi electrons onto nitrogen as a lone pair. (c) Move one lone pair from the left O into the N–O bond and simultaneously shift the N=O π\pi bond onto the right O as a lone pair. (d) Move one lone pair from the left O into the N–O bond only, leaving all other bonds and lone pairs unchanged.

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