Why Does the Central Carbon Have a Positive Charge?

  • Thread starter Thread starter alingy1
  • Start date Start date
  • Tags Tags
    Structure
Click For Summary

Discussion Overview

The discussion revolves around the concept of resonance structures in organic chemistry, specifically focusing on a central carbon atom that carries a positive charge, known as a carbocation. Participants explore the stability of such structures and the implications for reaction mechanisms.

Discussion Character

  • Exploratory, Technical explanation, Conceptual clarification, Debate/contested

Main Points Raised

  • One participant questions the stability of a central carbon with a positive charge and its ability to fill its octet, expressing confusion over the concept.
  • Another participant explains that the structure is a carbocation, noting its instability but also its role as a transient intermediate in various organic reactions.
  • A reference to "doubly allylic" carbocations is made, suggesting that multiple resonance structures can be drawn for such cases.
  • One participant claims to have identified three resonance structures and seeks confirmation, indicating a willingness to correct any mistakes.
  • Another participant suggests that more than three resonance structures can be drawn, but emphasizes that not all are significant contributors to the actual molecule's nature, implying a focus on stability in resonance structures.

Areas of Agreement / Disagreement

Participants express differing views on the number of resonance structures that can be drawn and their significance, indicating that the discussion remains unresolved regarding the optimal representations of the carbocation.

Contextual Notes

There are limitations regarding the assumptions made about resonance structures and the definitions of stability in this context, which remain unresolved.

alingy1
Messages
325
Reaction score
0
I was looking at this problem. It says I should write appropriate resonance structures. But, even with resonance, I do not see how a carbon cannot fill its octet. Why does the carbon in the middle have a positive charge. Is that not unstable?
 

Attachments

  • Screen Shot 2014-05-28 at 11.12.30 AM.png
    Screen Shot 2014-05-28 at 11.12.30 AM.png
    1,018 bytes · Views: 496
Physics news on Phys.org
The structure you have drawn is known as a carbocation. Although these structures are indeed very unstable, they are often transient intermediates in many reactions, and understanding their resonance structures can aid in understanding how these intermediates react in various organic reaction mechanisms (e.g. in unimolecular nucleophilic substitution and unimolecular elimination reactions.)
 
See: Allylic Carbocation.

In your case it is "doubly allylic" so you should have several resonance structures available. Can you draw them now?
 
I could find three! If you could confirm me the number that would be great! If they are wrong, I am fully ready to draw them out fully.
 
Well, you could technically draw many more resonance structure than simply three. It doesn't mean that all of them will be contributors to the true nature of the actual molecule though. I guess for the typical O-chem question where there it is implied that the most stable resonance structures should be drawn, then the answer is the first structure you posted and two more. So three total. You can post a picture for us to double check that you are doing it properly.
 

Similar threads

  • · Replies 9 ·
Replies
9
Views
13K
  • · Replies 2 ·
Replies
2
Views
3K
  • · Replies 9 ·
Replies
9
Views
3K
Replies
1
Views
3K
Replies
1
Views
2K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 11 ·
Replies
11
Views
11K
  • · Replies 7 ·
Replies
7
Views
4K
Replies
1
Views
7K
  • · Replies 2 ·
Replies
2
Views
3K