Linked Questions

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How does conjugation increase the stability of a compound

I have read that the stability of a compound is increased by conjugation, which allows electrons to delocalise and thus be more spread around the molecule. I'm struggling to understand how this ...
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1answer
226 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 ...
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Resonance structures and mechanism

I wrote the following resonance structures and our teacher wants us to write the curved arrows showing the mechanism as well... I was wondering if it's okay to show in which direction the mechanism ...
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1answer
77 views

How does resonance fail in approximating chemical structures?

In the book "Concise Inorganic Chemistry" by Prof. JD Lee, it says here: These contributing structures do not actually exist. The $\ce{CO3^2-}$ does not consist of a mixture of these structures, ...
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1answer
93 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?
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2answers
4k 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 ...
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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,...
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6answers
51k 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{...
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1answer
177 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 ...
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249 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 ...
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2answers
380 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 ...
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1answer
7k 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?
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1answer
16k 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. ...
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1answer
164 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 ...
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2answers
6k 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 ...

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