Linked Questions

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?
5
votes
1answer
709 views

Where do the lone pairs go in the “true” resonance structure?

Consider the "true" resonance structure of $\ce{CO3^2-}$: The bottom diagram leaves out the 2 lone pairs, so 4 electrons disappeared in the bottom image as compared to the top one. Are these ...
4
votes
1answer
138 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 ...
4
votes
1answer
618 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 ...
3
votes
1answer
64 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, ...
3
votes
1answer
3k views

How to explain (non-/anti-) aromaticity in fulvene with the help of resonance structures?

Can someone please explain why the resonance structures of fulvene 1 is non-aromatic and 2 is anti-aromatic? Why is fulvene non-aromatic, even though it has $4\pi$-electrons and no $\mathrm{sp^3}$ ...
3
votes
1answer
2k views

Are resonating structures real or not? [duplicate]

We say that hybrid structure is real. It has distinct properties as compared to its Resonating Structure. Is it because that all the experiments we carry out are on a sample, lots of molecules are ...
3
votes
1answer
688 views

Resonance in ozone and benzene [duplicate]

In inorganic chemistry, I learnt that stability of some atoms like ozone cannot be explained by one structure alone and hence the hybrid of possible structures is taken and assumed to be the structure ...
1
vote
1answer
70 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
vote
1answer
93 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 ...
0
votes
1answer
188 views

Generalizations regarding functional groups on benzene ring

While studying several organic mechanisms (high school level), I came to an interesting generalization. I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then ...
-1
votes
1answer
132 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 ...
2
votes
0answers
108 views

Mechanism of Biosynthesis of Terpenes

There is a specific part of the biosynthesis of terpenes that makes me confused: According to this mechanism, the double bond of the isopentenyl pyrophosphate attacks the primary carbocation, when it ...
0
votes
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,...
0
votes
0answers
204 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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