Linked Questions
33 questions linked to/from What is resonance, and are resonance structures real?
3
votes
2answers
70 views
Why does delocalization (only) occur in molecules represented by resonance hybrids?
Before I start this question, I am aware tha
Electrons in all molecules are delocalized to some extent
Delocalization is a the phenomenon and resonance is an attempt to explain it.
When I asked this ...
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 ...
4
votes
1answer
1k 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
31 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
102 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
173 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?
3
votes
1answer
2k 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
0answers
53 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
341 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 ...
-1
votes
1answer
208 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 ...
3
votes
4answers
6k 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 ...
4
votes
1answer
332 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 ...
5
votes
2answers
12k 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 ...
4
votes
1answer
906 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 ...
2
votes
0answers
145 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 ...