Why Does This Structure Show Resonance?

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Discussion Overview

The discussion revolves around the concept of resonance in molecular structures, specifically addressing why nitrogen, which is more electronegative than carbon, can participate in resonance despite this property. The conversation includes theoretical considerations and personal interpretations of resonance in chemical bonding.

Discussion Character

  • Debate/contested
  • Conceptual clarification
  • Homework-related

Main Points Raised

  • One participant expresses confusion about why nitrogen would show resonance by donating an electron to carbon, given its higher electronegativity.
  • Another participant references the definition of resonance, suggesting that molecules can exist as hybrid forms due to different covalent bond structures.
  • Some participants note that the electronegativity difference between nitrogen and carbon is not significant (around 0.5 units), which may allow for resonance to occur.
  • There is a suggestion that nitrogen can form different bonds with adjacent carbon atoms, implying the possibility of resonance structures regardless of electronegativity.
  • A later reply mentions that resonance can occur even if nitrogen forms a positive charge through a triple bond, indicating that electronegativity does not prevent resonance.

Areas of Agreement / Disagreement

Participants express differing views on the role of electronegativity in resonance, with no consensus reached on whether nitrogen's electronegativity should inhibit its ability to participate in resonance structures.

Contextual Notes

Some participants indicate that their understanding of resonance is limited, and there are references to specific molecular structures (like benzene) that may complicate the discussion. The conversation reflects a mix of personal interpretations and theoretical knowledge without resolving the underlying questions.

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Homework Statement


Why does the following structure show resonance?
347g1sw.jpg



Homework Equations





The Attempt at a Solution


The question was given by my teacher and he said that yes it will show resonance. But i still can't able to make it out why would it show resonance? The point is Nitrogen is more electronegative than Carbon and therefore should not show resonance but yet it does. It passes one of its electron from the lone pair to the carbon and makes a covalent bond. I don't agree with this because nitrogen is more electronegative and should avoid giving its electron to the carbon.

Any help is much appreciated.
Thanks! :smile:
 
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Can i expect a reply? :rolleyes:
 
Hi Pranav-Arora! :smile:

I just looked up the wikipedia definition of resonance.

Turns out that if you can form covalent bonds in different ways, the actual molecule is neither, but a hybrid form in between.

As it is, benzeen (C6H6) has 2 different covalent bond structures as you can see here:
350px-Benz3.svg.png

Resonance structures of benzene

The same would be true if you replace one of the carbon atoms by a nitrogen atom.
 
I like Serena said:
Hi Pranav-Arora! :smile:

I just looked up the wikipedia definition of resonance.

Turns out that if you can form covalent bonds in different ways, the actual molecule is neither, but a hybrid form in between.

As it is, benzeen (C6H6) has 2 different covalent bond structures as you can see here:
350px-Benz3.svg.png

Resonance structures of benzene

The same would be true if you replace one of the carbon atoms by a nitrogen atom.


*At least somebody cared to reply, thanks! :smile:*

I already know about the things you just posted and that's not the main problem for me. I asked why the nitrogen atom would ever pass its electron to carbocation even if it is more electronegative. Nitrogen should not give its electron to carbon due to higher electronegativity character.
 
The difference is not that high, around 0.5 unit.
 
Pranav-Arora said:
*At least somebody cared to reply, thanks! :smile:*

Have you considered that there's just not that many people around PF that know about this stuff? :wink:
I only know because I looked it up.

Now if you had some more questions on math or physics...


I already know about the things you just posted and that's not the main problem for me. I asked why the nitrogen atom would ever pass its electron to carbocation even if it is more electronegative. Nitrogen should not give its electron to carbon due to higher electronegativity character.

Seems to me that nitrogen can form different bonds with the 2 carbon atoms next to it regardless of its electronegativity.
This would imply a resonance structure.
(But I'm not a specialist. :shy:)
 
Borek said:
The difference is not that high, around 0.5 unit.

Only 0.5? lol

What if we replace Nitrogen with Oxygen?

I Like Serena said:
Now if you had some more questions on math or physics...

Don't talk about that stuff, i have already lost interest in it. :smile:
 
Last edited:
Pranav-Arora said:

Homework Statement


Why does the following structure show resonance?
347g1sw.jpg

Homework Equations


The Attempt at a Solution


The question was given by my teacher and he said that yes it will show resonance. But i still can't able to make it out why would it show resonance? The point is Nitrogen is more electronegative than Carbon and therefore should not show resonance but yet it does. It passes one of its electron from the lone pair to the carbon and makes a covalent bond. I don't agree with this because nitrogen is more electronegative and should avoid giving its electron to the carbon.

Any help is much appreciated.
Thanks! :smile:

you can make a triple bond on nitrogen making it positive so yes there is resonance.
EN doesn't stop anything from performing resonance. Except most likely your prof will say not to touch the benzene ring.
 

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