Linked Questions

22
votes
3answers
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 ...
16
votes
2answers
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 ...
13
votes
6answers
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{...
10
votes
4answers
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 ...
8
votes
2answers
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 ...
8
votes
3answers
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.
7
votes
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 ...
7
votes
3answers
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 ...
6
votes
1answer
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. ...
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
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 ...
5
votes
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 ...
5
votes
1answer
736 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 ...
5
votes
2answers
352 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 ...
4
votes
1answer
681 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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