Linked Questions

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1answer
64 views

Why does coumarin predominantly exist in keto form?

By applying the logic that phenol exists in enol form rather than keto form as it attains aromatic character, why is it not the case in coumarin?
1
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1answer
67 views

Which of the resonance structures is more stable?

I am quoting a rule on resonance from Organic Chemistry by T.W. Graham Solomons, Craig B. Fryhle, 12th edition, page 25. Structures in which all the atoms have a complete valence shell of ...
7
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2answers
3k views

What is the “resonance hybrid” of benzene?

In my book, to explain the structure of benzene, it referred to the idea of resonance: The idea of resonance is that the actual molecule is a definite structure that is a hybrid of two or more ...
0
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0answers
32 views

Stability and Resonance [duplicate]

The linked answers do attempt to clarify on 'stability' but I wanted an answer with specific connection to resonance. For example, the ethanoate ion can exist in many forms but, as we know from data,...
13
votes
6answers
46k views

How to determine the least stable resonance structures out of a given set?

So I was "happily" doing organic chemistry homework when I came across this question: For 1-methoxy-1,3-butadiene, which of the following resonating structure is the least stable? $$\begin{...
4
votes
1answer
125 views

Can a molecule be achiral whilst it's resonance form chiral?

I'm trying to work out whether methylphenylsulfoxide is a chiral molecule. It is my understanding that the sulfur uses sp2 hybridised orbitals. Why is this? The central sulfur atom is bound to 3 ...
0
votes
0answers
182 views

Which is most stable resonance structure of 4-nitrophenoxide ion?

According to my coaching module the first structure is more stable. Why is this so? I feel both must be approximately equally stable since negative charge is on oxygen in both cases. Would someone ...
5
votes
2answers
337 views

What is the correct way to verify a structure's geometry, for example for benzene?

My goal is to compare a calculated bond length with experimental data. Benzene is obviously common enough to expect sufficient experimental data to be available for it on the internet. I have found ...
6
votes
1answer
6k views

What is the order of stability of the resonance structures of furan?

I want to know which are the most stable furan resonance structures. I know that structure number 1 is the most stable, but which one comes after?
6
votes
1answer
13k views

Structures for NO+ (Nitrosonium)

There are two possible structures for Nitrosonium : In the first structure, there is a +1 Formal charge on Oxygen, whereas, In the second structure, there is a +1 Formal charge on Nitrogen. Q. ...
-1
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1answer
120 views

Resonance structure and stability

Does the existence of resonance structures always translate as stability? I've been taught that resonance structures generally "spread out" charge in order to compensate for deficiency or excess of ...
5
votes
2answers
4k views

What is the most “important” resonance structure of SCN⁻?

Numerous online references say that $\ce{SCN-}$ has two resonance structures: I am wondering why this structure is not also possible? I expect structure 3 to be rare because of the high formal ...
16
votes
2answers
581 views

What are the important implications to the field of chemistry, if any, of the recently confirmed hexavalent carbon species?

I’m struggling to understanding the true nature and implications of recent confirmations of the existence of stable species containing carbon atoms bound six (in another case 5) other carbon atoms. Is ...
6
votes
1answer
220 views

If I can't draw resonance structures for a pi system, does that mean it doesn't exist?

Whilst trying to answer this question I came across an interesting situation regarding the relationship between resonance structures and molecular orbitals. There are two places that you can ...
4
votes
1answer
586 views

VSEPR theory, chemical bond and quantum mechanics

VSEPR theory correctly predicts the shapes of many symmetry-broken molecules such as $\ce{H2O}$ and $\ce{NH3}$. Take $\ce{NH3}$ for example. In VSEPR theory, the nitrogen atom is (approximately) at ...

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