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#1 2011-09-10 14:23:39


Resonance structure of nitrogen dioxide

Help with nitrogen dioxide organic chemistry structure question!?
I have this one problem left on my homework that I cannot seem to figure out for the life of me. It says:

"Draw resonance contributors for the following species, showing all the lone pairs. (Copy and paste the given template as many times as necessary. Assign lone pairs, radical electrons, and atomic charges where appropriate.)

Indicate the most stable resonance contributor. (If multiple resonance forms are equally stable, enter all forms.)"

It has no charge, I know that. It's not supposed to have any charges on it, and according to my professor, there should be a radical (an unbonded single electron) on the oxygen that does have a single bond. The resonance structure is the radical being shared between the two. I know all of this for sure, but no matter which answer I try to use, it's never right. Help, please?

Below are the resonance structures one can draw for nitrogen dioxide (NO2). All structures contain an unpaired electron. The two radicals can combine to for an electron pair. Thus NO2 forms and equilibrium with N2O4.

I am uncertain of which form should be preferred, nor data that would support that assignment. However, the data does support a longer N-O bond suggesting that B is in resonance with A or C with C'.



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