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### 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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### 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 ...
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 ...
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,...
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{...
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 ...
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 ...
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 ...
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?
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. ...
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 ...
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 ...
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 ...
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 ...