Linked Questions

2 votes
0 answers
70 views

Which methoxy- and nitro-substituted azulene has the lower ground state energy?

My contention is that the first azulene structure, with the nitro group on the aromatic cyclopentene ring has a lower ground state energy, as the negative charge can not only resonate into the nitro ...
big_yoshi's user avatar
-1 votes
2 answers
296 views

Why does the conjugate base of peracetic acid not have any resonance structures?

Peroxyacetic acid, $\ce{CH3C(O)OOH}$ has its anion form when a proton is detached, like $\ce{CH3C(O)OO-}$. I think it can have two resonance forms like I drew (even though they have several charge ...
NIH's user avatar
  • 19
0 votes
1 answer
148 views

What is resonance in actuality? (How does electron sharing, bond formation, and overlapping of orbitals take place in resonance hybrids?) [duplicate]

In this post I got an answer to the question "what is resonance". What I understand overall is that "resonance is not something really happening physically, it is just an idea to make ...
Shinchan Nohara's user avatar
1 vote
1 answer
306 views

Does the same name represents all resonance and hybrid structure of a molecule?

The name chlorobenzene represents the following molecule. But the molecule shows resonance and its resonating structures are So does the same name represents all the resonance structures? Does it ...
Osmium's user avatar
  • 222
2 votes
0 answers
251 views

Does 'aromaticity' apply to individual resonance structures or the hybrid?

When we define the aromaticity of a compound, is it meant to describe the resonance hybrid of the compound, or for individual resonance structures of the compound? I think the latter is wrong because ...
Acc2's user avatar
  • 195
4 votes
1 answer
490 views

How to understand the role of the lone pair on the molecular structure when it participates in resonance?

I'm a little confused as to why we ignore the effect the lone pair has on the geometry of the molecule when it is participating in resonance. Wouldn't it be the case that the molecule is actually in ...
Andrea B.'s user avatar
  • 157
-4 votes
1 answer
884 views

In benzene and 1,3-cyclohexadiene, which one has greater C=C bond length? [closed]

In benzene and 1,3-cyclohexadiene, resonance will occur, so both will have a partial pi character. Technically, all bonds in benzene have partial pi character, whereas in 1,3-cyclohexadiene, some have ...
confused_Student's user avatar
3 votes
2 answers
1k 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 ...
Vulgar Mechanick's user avatar
4 votes
1 answer
2k views

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

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 ...
Vishnu's user avatar
  • 2,060
0 votes
0 answers
46 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 ...
Geek's user avatar
  • 89
3 votes
1 answer
147 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, ...
Micelle's user avatar
  • 181
1 vote
1 answer
388 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?
Abhigyan's user avatar
  • 160
4 votes
1 answer
4k views

Which of the canonical structures contributes more to resonance hybrid?

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 ...
Chakravarthy Kalyan's user avatar
0 votes
0 answers
63 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,...
Sal_99's user avatar
  • 207
0 votes
0 answers
642 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 ...
Hema's user avatar
  • 667

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