WTF is this molecule?

[Airplay355]

I just took an OChem midterm and we had to draw the resonance structures of a molecule. I'm trying to find that molecule so I can see if I did it right.

It looked like a cyclohexane with an O in it (in the ring) and an N in the ring too, a methyl group off the N, a double bond between two of the carbons in the ring and a positive charge on one of the remaining carbons.

I guess a better way to explain it would be if the N with the methyl group was #1 in the ring going clockwise #2=C #3=O #4=C #5=C #6=C+ with the double bond between C4 and C5.

Can anyone tell me what molecule this is and what the resonance hybrid and resonance forms are?

Thanks!!

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[JA Prufrock]

If I understood your description correctly, there are going to be a number of resonance forms, since you can move that positive charge around. In one form you could use the lone pair from the N to double bond with the carbon cation so that the positive charge now rests on the nitrogen. This gives you a resonance form with 2 double bonds and all atoms having an octet.

In another form you could break the existing double bond and transfer those electrons so that the 5 and 6 position now have a double bond, leaving the 4 position with a positive charge. This resonance form could then be converted to another one by taking a lone pair off of oxygen and using it to double bond with the carbon cation at the 4 position. The oxygen now carries the positive charge This once again gives you a resonance form with 2 double bonds and all atoms with an octet.

oh and btw, I don't really know what kind of classification this molecule falls under. I would say cyclic ether, but I don't know if that works with the N in the ring.

 

[BloodySurgeon]

SDN is not a place for homework or test questions. I will now close this thread.