[trinhn812]

So here's another orgo problem that's driving me nuts. http://i45.photobucket.com/albums/f84/azncrombie/mysolution.jpg

It wants me to: Can you draw a resonance structure of this molecule without any formal charges and with an octet on every atom? Think three-membered ring...

I don't think its possible cause I need two more electrons to make oxygen octet. Here's what I did:

http://i45.photobucket.com/albums/f84/azncrombie/question14.jpg
Carbon can't take any more bonds, and I don't think I can get the electrons from benzene over to oxygen.

[trinhn812]

woops, I made the first picture, and they gave me the second

[nj_bartel]

Think three membered ring

big hint there

[trinhn812]

I'm not sure what a three member ring looks like. Doesn't a ring require all atoms to be connected, but in this case O and N is only connected to C and not to each other.

[trinhn812]

Okay so I connected the N to the O, but how does this make it a resonance? I just made a new bond between the atoms that didn't exist before.

[nj_bartel]

http://homepage.smc.edu/kline_peggy/Organic/Rules_for_Resonance.html

You're not moving nuclei

[AWK]

I think , the molecule should contain two hydrogen atoms more,ie:
C₆H₅CONH₂

[sjb]

I think , the molecule should contain two hydrogen atoms more,ie:
C₆H₅CONH₂

It's possible, but there are also oxaziridines, which may be what nj_bartel is driving at..?

[nj_bartel]

That is what I was getting at.  It's just a find this resonance structure problem, doesn't necessarily need to be a really stable molecule.