April 25, 2024, 04:19:06 AM
Forum Rules: Read This Before Posting


Topic: Electrons delocalized  (Read 4689 times)

0 Members and 1 Guest are viewing this topic.

Offline Imo

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
Electrons delocalized
« on: April 07, 2012, 12:16:37 AM »
What of theses have resonance structures ? electrons delocalized...
Is the 1,2,3,5 and 6?
http://imageshack.us/photo/my-images/705/semttulocak.png/

Offline Schrödinger

  • Chemist
  • Sr. Member
  • *
  • Posts: 1162
  • Mole Snacks: +138/-98
  • Gender: Male
Re: Electrons delocalized
« Reply #1 on: April 07, 2012, 03:51:35 AM »
Yes, the others are isolated systems. No resonance is possible in them
"Destiny is not a matter of chance; but a matter of choice. It is not a thing to be waited for; it is a thing to be achieved."
- William Jennings Bryan

Offline Imo

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
Re: Electrons delocalized
« Reply #2 on: April 07, 2012, 07:20:26 PM »
Why 3 has resonance?

Offline Imo

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
Re: Electrons delocalized
« Reply #3 on: April 07, 2012, 09:27:03 PM »
I think this : http://imageshack.us/photo/my-images/171/27743918.png/

But will have one charge negative, not positive. Can anyone make the resonance for me? or explain...

Offline Schrödinger

  • Chemist
  • Sr. Member
  • *
  • Posts: 1162
  • Mole Snacks: +138/-98
  • Gender: Male
Re: Electrons delocalized
« Reply #4 on: April 07, 2012, 11:48:10 PM »
No. Once that pi bond moves to O+, it becomes neutral and the adjacent carbon becomes positively charged, because it has just lost a pi bond's electron. So, basically, the positive charge migrates from O to C and if you keep this up with the ext pi bond, you can see that the potive charge is delocalized over the entire ring.
"Destiny is not a matter of chance; but a matter of choice. It is not a thing to be waited for; it is a thing to be achieved."
- William Jennings Bryan

Offline Imo

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
Re: Electrons delocalized
« Reply #5 on: April 08, 2012, 01:16:44 AM »
Is this http://imageshack.us/photo/my-images/854/68570334.png/   ?
I only can get 1 structure of resonance. A pi bond breaks down and only it...

Offline Schrödinger

  • Chemist
  • Sr. Member
  • *
  • Posts: 1162
  • Mole Snacks: +138/-98
  • Gender: Male
Re: Electrons delocalized
« Reply #6 on: April 08, 2012, 09:11:32 AM »
Correct. Now use the other pi bond that is in conjugation with the positive charge (the C=C double bond has a pi bond you can use)
"Destiny is not a matter of chance; but a matter of choice. It is not a thing to be waited for; it is a thing to be achieved."
- William Jennings Bryan

Offline Imo

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
Re: Electrons delocalized
« Reply #7 on: April 08, 2012, 12:39:40 PM »
How is the solution for 2 ?
http://imageshack.us/photo/my-images/268/81839705.png/

I did it, but anything is wrong...

 For 6 these are only 2 structures of resonance?
http://imageshack.us/photo/my-images/138/molk.png/
http://imageshack.us/photo/my-images/40/moll.png/


Offline Imo

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
Re: Electrons delocalized
« Reply #8 on: April 09, 2012, 07:30:04 AM »
Forget the previous post ... what worries me is this:
To draw resonance structures of the compound, usually write:
http://imageshack.us/photo/my-images/713/15616772.png/
But can or should I do so?
http://imageshack.us/photo/my-images/339/85919308.png/
because it is more detailed...is wrong?


Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Electrons delocalized
« Reply #9 on: April 09, 2012, 09:50:55 AM »
what worries me is this:
To draw resonance structures of the compound, usually write:
http://imageshack.us/photo/my-images/713/15616772.png/
But can or should I do so?
http://imageshack.us/photo/my-images/339/85919308.png/
because it is more detailed...is wrong?

Wrong? Sort of. It is probably more wrong because of convention than by fact. What is wrong is to have ten electrons surrounding carbon. Clearly the transition state of an SN2 reaction has ten electrons and an alternate resonance form of a nitro nitrogen has ten electrons, so seeing ten electrons may not be so wrong. However, the convention is to maintain the octet rule in drawing resonance structures. So the first example correctly simultaneously breaks a bond to avoid ten electrons. You should follow that example. I would also advocate drawing the curved arrows as well. Although you did not make any errors in the resultant electron movements, the curved arrows are very useful in determining how they should move. It is not unusual for a student to correctly draw a curved arrow, but upon looking at a structure think the electrons should have a different arrangement and draw a resonance structure inconsistent with the curved arrows.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Imo

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
Re: Electrons delocalized
« Reply #10 on: April 09, 2012, 06:34:20 PM »
the convention is to maintain the octet rule ?
But here: http://imageshack.us/photo/my-images/824/digitalizar0040.jpg/

The second, with O+, yours structures of resonances dont complete the octet rule...the carbons will have 7 eletrons...yeah? 
is correct?

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Electrons delocalized
« Reply #11 on: April 10, 2012, 12:52:54 AM »
Okay, my error in not explaining fully. The octet rule applies to not exceeding eight electrons. Granted, carbon for example can have fewer than eight electrons and one can find many examples in which it does not have eight. I meant you cannot have ten (valence) electrons around B, C, N, O, or F.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Sponsored Links