April 29, 2024, 06:25:51 AM
Forum Rules: Read This Before Posting


Topic: Urea Resonance Structures  (Read 9332 times)

0 Members and 1 Guest are viewing this topic.

Offline benjaminjado

  • Very New Member
  • *
  • Posts: 1
  • Mole Snacks: +0/-0
Urea Resonance Structures
« on: September 04, 2009, 12:56:17 PM »
I'm new to organic chemistry and trying to figure out resonance structures for urea (NH2)2-CO.
I don't know if there are two or three:

1) The greatest contributor to the character of the resonance hybrid should be the structure with the double bond between C and O.

2)  A second structure has a double bond between C and N, with a (+) charge on the double-bonded N and a (-) charge now on the O.

3?)  If I put a double bond between the C and "nitrogen-two" instead of "nitrogen-one," is that a different structure or the same?  How can I tell?

Offline azmanam

  • Chemist
  • Sr. Member
  • *
  • Posts: 1417
  • Mole Snacks: +160/-24
  • Mediocrity is a handrail -Charles Louis d'Secondat
Re: Urea Resonance Structures
« Reply #1 on: September 04, 2009, 02:57:00 PM »
Even though it looks the same, they are different.  As proof, if we arbitrarily set the single bond distance to 1, and the double bond distance at.5 (bc double bonds are shorter thansingle bonds), then the resonance hybrid for urea has all 3 bond lengths at apps 0.75.

Your analysis is right on
Knowing why you got a question wrong is better than knowing that you got a question right.

Sponsored Links