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 ...
707 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 ...
1k views

### Does benzene structure stand for a single resonance form or the whole molecule?

It is known that benzene has two main resonance forms Often we still draw benzene molecule as one of them My question is, actually when we draw the lower figure, do we refer to the whole benzene ...
666 views

### What is the isomer distribution in monosubstituted fluorobullvalene?

Bullvalene (tricyclo[3.3.2.02,8]deca-3,6,9-triene) is a fluxional molecule able to interconvert any two carbon atoms through a series of degenerate Cope rearrangements (for more information, see the ...
48k 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{...
595 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 ...
3k views

### Rearrangement of double bonds

Consider: I found these rearrangements, but I could not understand what the mechanism is behind this. When I searched on the Internet I found the Wikipedia page Di-pi-methane rearrangement.
15k 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. ...
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 ...
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 ...
673 views

### Trying to understand the statement: 'Resonance is not a flickering between the contributing states. '

So, the famous resonance definition: it is the weighted average of different Lewis structures.... Well, this is purely wrong. Resonance is nothing but quantum 'superposition of the wavefunctions ...
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?
4k views

### Why does HNO2 not have resonance?

A question on the 1996 AP Chemistry Free Response asks: The $\ce{N-O}$ bonds in the $\ce{NO2-}$ ion are equal in length, whereas they are unequal in $\ce{HNO2}$. Explain. Since the nitrogen ...
811 views

### Stability and resonance structures

In school they ask us to count the number of resonance structures in different organic compounds to determine it's stability. The one with more resonance structures is more stable. Is this notion ...
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 $\mathrm{sp^3}$ ...
741 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 ...
684 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 ...
354 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 ...
236 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 ...
69 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, ...
145 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 ...
192 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 ...
76 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?
219 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 ...
144 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 ...
121 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 ...
101 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 ...