Why is this showing resonance?

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In summary, the conversation discusses the concept of resonance and its application in a specific structure involving a nitrogen atom. The question is raised about why the nitrogen atom, being more electronegative than carbon, would pass its electron to the carbon and form a covalent bond, which goes against the general understanding of electronegativity. It is explained that resonance structures involve hybrid forms of molecules and that the difference in electronegativity between nitrogen and carbon is not significant enough to prevent the formation of resonance structures. It is also mentioned that one can create a triple bond on nitrogen, leading to resonance. Overall, the conversation provides a brief explanation of the concept of resonance and its application in a specific structure.
  • #1
Saitama
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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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  • #2
Can i expect a reply? :rolleyes:
 
  • #3
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.
 
  • #4
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.
 
  • #5
The difference is not that high, around 0.5 unit.
 
  • #6
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:)
 
  • #7
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:
  • #8
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.
 

Related to Why is this showing resonance?

1. Why do some compounds show resonance?

Resonance is a concept in chemistry that explains the delocalization of electrons within a molecule. This occurs when a molecule has multiple Lewis structures that can be drawn, each with different arrangements of double bonds. The actual structure of the molecule is a hybrid of all the possible Lewis structures, resulting in resonance.

2. How does resonance affect the stability of a molecule?

Resonance increases the stability of a molecule because it distributes the charge over a larger area, making the molecule less reactive. This is due to the delocalization of electrons, which results in a more stable electronic structure.

3. Can resonance occur in all types of molecules?

Resonance can occur in all molecules that have multiple Lewis structures that can be drawn. This includes molecules with alternating single and double bonds, as well as molecules with lone pairs of electrons on adjacent atoms.

4. Why is resonance important in organic chemistry?

Resonance is important in organic chemistry because it helps explain the reactivity and stability of molecules. It also plays a crucial role in determining the physical and chemical properties of organic compounds.

5. How can we predict if a molecule will show resonance?

We can predict if a molecule will show resonance by examining its Lewis structure and determining if there are multiple ways to arrange the double bonds within the molecule. This is also known as having multiple resonance structures.

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