Questions tagged [resonance]

Resonance refers to the representation of the electronic structure of a molecular entity in terms of contributing structures. The tag should be applied to any question that concern resonance structures or resonance energy. This tag should not be applied to questions about aromatic compounds (use the [aromatic-compounds] tag instead)

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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 ...
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Number of resonance structures of nitrobenzene

I was studying about the resonance and here's my doubt: How many resonating structures are there in nitrobenzene? Is it 5 (as drawn) or is it 4 because first and the last structures are same or is it ...
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Why does the phosphate ion have resonance structures?

My first-year chemistry teacher depicted $ \mathrm{PO_{4}^{3-}}$ as exhibiting the resonance structure inset below this question. However, I can't figure out what diagramming rules (which is what ...
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Stability of carbocations

We know that if a structure has all equivalent resonance structures, then it will be highly stabilised. So then why benzylic carbocation is more stable than other cyclic allylic carbocations, though ...
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Origin of different colour for thio analogue of indigo from blue to red

Why the thio analogue of indigo is red? What is the reason behind change of colour from indigo to red just by change of N to S. What I get is that there will be electronegativity, lone pair ...
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Are the lone pair electrons on an carbonyl oxygen in sp2 orbitals?

Carbonyl Group Double Bonds [...] One pair of the oxygen lone pairs are located in 2s while the other pair are in 2p orbital where its axis is directed perpendicular to the direction of the ...
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Why does O2NCl only have two resonance structures?

Why is it that $\ce{O2NCl}$ has only two resonance structures? More specifically, why is the Lewis drawing where $\ce{N}$ is double bonded to $\ce{Cl}$ not considered a resonance structure along with ...
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Find the order of acidic strength

Arrange the following in decreasing order of acidity I think it's S>P>R>Q (Q) forms an anti aromatic conjugate base. So its the least acidic compound here. (R) forms forms a conjugate base which is ...
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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 ...
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Effect of substituents on aniline C-N bond length

Which compound has larger $\ce{C-N}$ bond length, 4-aminobenzaldehyde (1) or aniline (2)? I think it's the second compound. $\ce{-CHO}$ is an electron withdrawing group. This means the electron ...
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What is a sigma complex?

According to Wikipedia, "sigma complex" refers to an arenium ion. The suffix "-ium" denotes a positively charged ion. So, it is correct to call the resonance structures in the below picture ...
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Is 2-oxobicyclo[2.2.1]heptan-1-ide resonance stabilized?

Is the following compound resonance stabilized? I think its not resonance stabilized because the p-orbital of carbanion and pure p-orbital of carbonyl carbon are not in same plane. So they can't ...
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Rotational Barriers - Amide and Hydroxamic Acid

Why the barrier to rotation about the $\ce{C-N}$ bond higher in an amide than it is in a hydroxamic acid? (MO-based explanation preferred)
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Is my reasoning for resonance structures correct?

given this picture, which resonance structure is correct? I'm thinking 1 and 3. You can't have 2 because the carbon which originally had a negative charge would be making 5 bonds, and you can't have 4 ...
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Why are the C-C bonds in benzene closer in length to double bonds than single bonds?

The $\ce{C-C}$ bonds in benzene are $\mathrm{140~pm}$ long which puts them in between single bonds and double bonds (given at $\mathrm{147-154~pm}$ and $\ce{134-135~pm}$ respectively, sourced from ...
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How to predict a good resonance structure?

I have to draw curved arrows to convert the above molecule to its resonance structure but I'm not entirely sure how. I believe the sulfur atom has one lone pair and the oxygen atom has 2 lone pairs. ...
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Stability of carbocation intermediates: secondary alkane versus primary allyl?

Say I have the following carbocations: The first is secondary; the second is resonance stabilized, but primary. Which is more stable and why? I've been looking around in my textbooks and haven't ...
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Why the H+ ion remains with the molecule even though there is no bond between it and hyperconjugative structure?

In hyperconjugation, it is known that form an $\alpha$ hydrogen, one $\sigma$ electron goes to the corresponding carbon carbon bond, and there is apparently or practically, no bond between the ...
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Why is sulfur dioxide more stable to UV radiation than ozone?

Ozone readily decomposes when impacted by UV radiation. Sulfur dioxide, having the same bond structure and valence electrons in each atom as ozone, is much more stable. Would someone please help ...
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Inductive effect of phenyl ring

I completely understand how phenyl group 'releases' or 'donates' electron through resonance, but how is that a phenyl group shows a weak -I effect, despite having electrons literally smeared on itself?...
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If both nitric acid and nitrate ion are stabilised through resonance, what makes the nitrate ion more stable in aqueous medium?

If both nitric acid and nitrate ion are stabilised through resonance, what makes the nitrate ion more stable in aqueous medium? Can the same argument be applied to nitrous acid and nitrite ion in ...
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Why is the original Pauling's theory of resonance that uses superposition of wavefunctions not used today?

I have recently studied superposition of states (also the famous Schrodinger's cat), measurement problem, decoherence & so on. I then read the resonance concept from Atkins' Physical Chemistry ...
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Why is the resonance concept not required in molecular orbital theory?

In valence bond theory, resonance plays a pivoting role; why isn't such concept needed in MO theory? Why is it told that "MO theory provides a global, delocalized perspective on chemical bonding"? (...
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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{...
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Which compound reacts faster in the Cannizzaro Reaction?

Which reacts faster in the Cannizzaro Reaction? a) $\ce{OHC-C6H4-NO2}$ b) $\ce{OHC-C6H4-OCH3}$ Obviously, a better hydride releasing group will react faster. Therefore my answer was b, as $\ce{-...
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Which has greater +R strength - toluene or anisole?

I read that resonance in toluene is initiated with the help of hyper-conjugation. Also hyper-conjugation is weaker than resonance/mesomeric effect. But, in toluene, its resonance is taking place with ...
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Why is it the middle ring of anthracene which reacts in a Diels–Alder?

I'm wondering why maleic anhydride adds to the middle cycle of anthracene, and not the outer two. I would have expected that a Diels–Alder with the outer ring would be better, because I expected a ...
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Is nitrogen of aniline sp² or sp³ hybridized? [duplicate]

I found a thread which discussed this which totally confused me. (refer to the part of the link which talks about $\ce{sp^2/sp^3}$) The question "How to rationalise the resonance structures and ...
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What are the correct resonance structures of nitrous oxide?

There was a question in one of my exam papers to draw the resonance structures for $\ce{N2O}$. These are the ones I drew, but they were not awarded marks: The ones in the marking scheme are as ...
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What are the resonance structures of 3-aminocyclohex-2-en-1-ylium?

How would you draw the resonance structure for the compound below: This is one of the resonance forms I think... but I'm sure there is another one too.
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PBP vs TBP geometry?

Why are the axial bond lengths greater than those of the equatorial bonds in a trigonal bi-pyramid (TBP) geometry molecule; but the opposite is true for pentagonal bi-pyramid (PBP) geometry molecules? ...
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Effect of different electron withdrawing/transition state stabilising groups in nucleophillic aromatic substitution

I have been asked the following question in my problem sheet: The only differemce between reaction A and reaction B is the electron withdrawing group that stabilises the anionic transition state ...
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Why should 2,6-Dimethyl-4-nitrophenol be more acidic than 3,5-Dimethyl-4-nitrophenol

I was trying to compare acidity of some organic compounds but can't understand some: Why should 2,6-dimethyl-4-nitrophenol be more acidic than 3,5-dimethyl-4-nitrophenol? I have been trying to ...
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Why is chloroethene said to be a conjugated system?

Why is chloroethene said to be a conjugated system?Is it because of p orbitals present in chlorine or something?
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Polarity of the nitrate ion

We observe that nitrate ion has a trigonal planar geometry according to its lewis structure and the VSEPR theory. Its resonance hybrid consists of three contributing structure -three probable double ...
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Hyper conjugation in acetic acid?

While comparing the relative stabilities of acetic acid and formic acid why don't we consider the 3 possible hyper conjugative structures which would stabilize the positive charge on carbon thus ...
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What are the resonance structures for chlorite anion?

What are the possible resonance structures for $\ce{ClO_2^-}$? Assigning one double bond to the structure makes for formal charges of $\ce{O(-1)-Cl(0)=O(0) <-> O(-1)=Cl(0)-O(-1)}$. It appears ...
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How to determine the bond order using the Lewis structure?

What are the steps to follow in order to determine which molecule has a higher bond order by drawing the Lewis structure? For example, with $\ce{CO}$ and $\ce{CO3^{2-}}$?
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Resonance structures of some aromatic compounds

Do compounds like tropolone, furan, and thiophene (which are aromatic) show resonance? If yes then what are the resonance structures that can be drawn? Also, do all aromatic compounds show resonance?
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What is the reasoning behind the resonating structure of halo-benzene? [closed]

Can anyone explain the resonating structure of halo-benzene? How does the transfer of an electron from the halogen atom to the α-carbon and from there to ß-carbon and so on take place?
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Why aryl halides are very less reactive towards nucleophilic substitution reactions? [duplicate]

I've often herd that aryl halides are very less reactive towards nucleophilic substitution reactions. One of the reasons for this I found was that there is resonance effect in the compound, but how is ...
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Reactivity of thioesters with respect to nucleophilic attack

Why are thioesters relatively reactive with regard to nucleophilic attack? Prof says to wait until pchem 3 when we learn about orbital symmetry. He also said that sulfur’s d-orbitals (?!) don't have ...
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Higher energy π HOMO

Which is higher in energy? Cyclohexanone enol or cyclohex-2-en-1-ol? Okay from what I understand a higher pi HOMO is synonymous with more nucleophilic. So I would expect cyclohex-2-en-1-ol to have ...
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Why is a hydroxyl group more activating than a methoxy group in electrophilic aromatic substitution?

Why is phenol more reactive towards electrophilic substitution than methoxybenzene? Isn't the lone pair on the methoxy group oxygen more available for participating in resonance into the ring than the ...
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Does resonance overrule hyper conjugation in terms of stability in alkenes? [closed]

Which of the following is more stable ? $\ce{CH2=C(CH3)-CH=CH2}$ $\ce{CH3-CH=CH-CH3}$ I was going for answer 2 because it has 6 hyper conjugative effects. I found the answer given to be ...
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In which all substituents does Inductive effect overpower Mesomeric effect?

In most substituents, the mesomeric effect is considered stronger and more dominating than the inductive effect. A notable exception are the halogens. The reason behind this has been well-...
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How accurate is this polar mechanism for the Diels-Alder reaction?

So the prof got to Diels-Alder without discussing it in the context of molecular orbital theory. Instead we got a resonance picture of what happens... this is what he told us: 1) 1,3-butadiene has ...
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Why do certain groups withdraw/ donate electron to double bond or conjugated system in resonance effect?

Why for the Resonance effect certain group of substituents/functional group donate electron from the double bond or to a conjugated system while some withdraw electron from the double bond or to a ...
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Why is there a need for resonance?

Why are we able to show structures of compounds with different position of electron, but with same position of them? Shouldn't the structure become unstable due to this? Let's take benzene for the ...
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Resonance structure of cyclobutadiene?

I studied cyclobutadiene as an anti-aromatic compound. But I am unable to draw the resonance structures for cyclobutadiene. Can anyone help me? What is the driving force for the resonance to start? ...