Linked Questions

3
votes
4answers
5k views

What is the CNC bond angle in methyl isocyanate?

Methyl isocyanate, $\ce{HC3NCO}$, is a toxic liquid which is used in the manufacture of some pesticides. What is the approximate angle between the bonds formed by the nitrogen atom in a molecule of ...
3
votes
1answer
754 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 ...
2
votes
2answers
937 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 ...
0
votes
0answers
23 views

How does actually negative charge travel in phenol from ortho to para to ortho? [duplicate]

When we say negative charge flows from ortho to para position, and electron density at ortho and para is more, where does electron actually stay at ortho and para? Is it at $p_\mathrm{z}$ orbital or ...
15
votes
4answers
52k views

How to determine the worst 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{...
4
votes
1answer
179 views

How to determine the relative contribution of resonance structures when different rules give contradictory outcomes?

In order to determine the relative contributions of resonance structures, my textbook gives the following rules (in order): The more covalent bonds a structure has, the higher it scores. Structures ...
0
votes
0answers
29 views

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 ...
3
votes
1answer
84 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, ...
1
vote
1answer
127 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?
7
votes
2answers
5k 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 ...
0
votes
0answers
42 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,...
4
votes
1answer
231 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 ...
0
votes
0answers
297 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 ...
5
votes
2answers
410 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 ...
6
votes
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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