We’re rewarding the question askers & reputations are being recalculated! Read more.

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)

Filter by
Sorted by
Tagged with
34
votes
4answers
5k views

What is resonance, and are resonance structures real?

My teacher told me about resonance and explained it as different structures which are flipping back and forth and that we only observe a sort of average structure. How does this work? Why do the ...
34
votes
1answer
3k views

Natural Bond Orbital analysis: Significance of stabilization energy determined by 2nd order perturbation

PREFACE: I am no expert on this topic. My questions at the bottom may be off base. I have some experience with symmetry-adapted perturbation theory (SAPT) when it comes to analyzing intermolecular ...
32
votes
3answers
2k views

Pauli exclusion principle and resonance

I've always been a bit uncomfortable with the concept of more than two electrons in a single orbital-like region(probability-wise) which occurs in resonance. This seems to disobey Pauli's exclusion ...
30
votes
1answer
43k views

Acidity of substituted phenols

Phenol has a $\mathrm pK_\mathrm a$ approximately equal to $9.9$. When one studies the acidity of chlorophenols, one notices the following: First of all, chlorophenols are more acidic than phenol, ...
21
votes
3answers
10k views

Which carbons in pyrrole have the highest electron density?

In pyrrole, which carbon atoms have the greatest electron density? In the resonance structures of pyrrole, all carbons can formally bear a negative charge, so it's not immediately obvious which one ...
21
votes
1answer
5k views

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? ...
21
votes
1answer
11k views

Stability Comparison between the Tropylium and Tricyclopropylcarbinyl Carbocation

Why is the Tropylium carbocation less stable than the tricyclopropylcarbinyl carbocation? The tricyclopropylcarbinyl carbocation undergoes a sigma-tropic rearrangement whereas tropylium is highly ...
21
votes
1answer
685 views

How does the cyclopropyl group influence conjugation and aromaticity?

While answering the question Why isn't cyclobutane planar?, I recollected that cyclopropane and its derivatives behave like double-bond compounds, e.g. a cyclopropyl group can potentially be ...
20
votes
2answers
8k views

How to rationalise the resonance structures and hybridisation of the nitrogen in a conjugated amine?

I was given the first structure, and then drew the other 5 resonance structures: First of all, are they correct? ChemBioDraw had some complaints, but as far as I can see there's the same number of ...
19
votes
2answers
11k views

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 ...
19
votes
3answers
5k views

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{-...
18
votes
4answers
9k views

Can ozone have a triangular structure?

The structure of ozone is traditionally depicted using two resonance forms: However, what I am wondering is instead of using such an idea to explain the structure why can't we show the structure of ...
18
votes
1answer
3k views

Why does depurination happen at a higher pH (or under less harsh conditions) than depyrimidation?

I've always wondered why the N-glycosidic bond, which connects the adenine or guanine purine bases to their sugars, was the easiest to cleave via acid hydrolysis, or why purines have the lowest ...
17
votes
3answers
56k views

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 ...
16
votes
3answers
20k views

How does Resonance stabilize a molecule?

How does resonance lower the potential energy of the molecule? Take $\ce{O3}$ as an example.
16
votes
3answers
34k views

Bond order for carbonate ion for resonance

I saw in a textbook that for carbonate ion, there are 3 resonance forms and the bond order is 1 and 1/3. So in general, how should we calculate the bond order for resonance structures? Is there any ...
15
votes
4answers
859 views

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 ...
15
votes
5answers
16k views

Is oxygen with a positive charge more stable? (comparison of canonical structures)

Which of the contributing structures of the resonance below is more stable? I'm watching a video lecture by a professor of my college where he puts this question to the class. The class ...
15
votes
2answers
801 views

Edges of graphite

I've been asked this question a few times, and while I think I know the answer, I'd like to know more. Graphite, as we know, is a sheet polymer. Since polymers are bound to be finite by physical ...
15
votes
1answer
13k views

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 ...
14
votes
2answers
677 views

Do non-classical carbanions exist?

There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any ...
14
votes
3answers
7k views

Do lone pairs on substituents (e.g. in aniline) count towards Hückel's rule?

Why is aniline aromatic? Doesn't it have 8 π electrons including the lone pair on nitrogen, thereby violating Hückel's rule? The way I see it, there are 6 π electrons from the benzene ring, and an ...
14
votes
1answer
8k views

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 ...
14
votes
1answer
575 views

Why can't antiaromatic compounds just escape planarity and become non-aromatic to avoid destabilization?

Why can't just all anti-aromatic systems lose planarity (and hence conjugation) and be non-aromatic like cyclooctatetraene ? ...
13
votes
3answers
2k views

Is the phenoxide ion aromatic?

Is the phenoxide ion aromatic? I read that technically it isn't aromatic because it violates some arcane rule, but I can't find any references in the literature. I don't see why it couldn't be ...
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{...
13
votes
3answers
9k views

Competing resonance and inductive effects in a substituted benzene

A molecule of phenol is much more inclined to under go an electrophilic substitution reaction than a molecule of benzene because the $\ce{-OH}$ group is highly reaction favoring. From what I ...
13
votes
3answers
15k views

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 ...
13
votes
2answers
8k views

Resonance stability: ester vs. thioester

My problem set solution cites: "Although sulfur is less electronegative than oxygen, overlap is a more important consideration. Sulfur is a member of the third period. As a consequence, a ...
12
votes
2answers
2k views

Regioselective enolate formation

Our professor only told us that A is favored, and B is not getting formed. I thought about the resonance structures and saw a contradiction to that what the prof told us. To be honest I think my ...
12
votes
1answer
5k views

Rationalizing the Planarity of Formamide

In formamide, the nitrogens appear to be $\ce{sp^3}$ hybridized, implying tetrahedral geometry. However, analysis shows that the molecule is actually very nearly planar with bond angles close to 120 ...
12
votes
1answer
178 views

What is the physical origin of conjugation?

I had a question about the origins of conjugation in conjugated molecules. Take two ethylenes as compared to butadiene. Huckel seemed to argue that conjugation was the result of pi-pi stabilization ...
12
votes
2answers
547 views

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 ...
11
votes
2answers
552 views

Which is the most acidic proton of (3Z)-3-ethylidenecyclopent-1-ene-1-carbaldehyde?

At first glance, I thought the most acidic protons would be the ones in red due to their proximity to the carbonyl. However, the answer key has the hydrogens in green as the most acidic. Can someone ...
11
votes
1answer
8k views

Does unsubstituted benzoic acid not show resonance due to steric effects?

My book says that benzoic acid does not show resonance as the carboxylate anion and the benzene ring are not in the same plane due to steric effects. But there aren't any large groups in the ortho ...
11
votes
1answer
2k views

Which of the following has higher enol content?

Which of the following has higher enol content? The enol form of (A) and (B) is: Both the enols have hydrogen bonding. If the oxygen were to accept the pi electrns from carbon forming a carbocation ...
11
votes
1answer
1k views

Resonance in carbocation derived from allenes

During a reaction if addition on one of the $\pi$ bonds of an allene (containing even number of $\pi$ bonds like $\ce {H2C=C=CH2}$) takes place then a carbocation is formed. To decide the position of ...
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 ...
10
votes
3answers
10k views

Which is the most acidic hydrogen in vitamin C

I thought it would be the lower first $\ce{-OH}$ because it's close to the double bond with oxygen, so I thought there would be more electron withdrawal from the oxygen atom due to its ...
10
votes
3answers
3k views

Why is diene more reactive than alkene?

The chemical reduction of 1,3-butadiene with sodium in alcohol gives mainly the 1,4-addition product that is but-2-ene. Under these condition the isolated double bond are not reduced. This suggest ...
10
votes
2answers
7k views

Ozone resonance structure: differing opinions

I've always thought that the two-form resonance structure of ozone was the scientific concensus (from Wikipedia]: Then today I found two other opinions. A three-form structure: And a four-form ...
10
votes
2answers
4k views

Which are the differences between resonance Raman and fluorescence?

If the fluorescence is the re-emitting of a photon with a larger wavelenght due to the transition from a higher energy state to a lower energy state the case of resonance Raman (where there aren't any ...
10
votes
2answers
13k views

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?...
10
votes
1answer
9k views

Why does delocalization of π electrons bring stability?

My book mentions that Delocalization of $\pi$ electrons makes a compound stable as the process of delocalization involves loss in internal energy. This is the synopsis of resonance. But how does ...
9
votes
2answers
15k views

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 ...
9
votes
2answers
3k views

Participation of Pi-bonds and lone pairs in resonance

Below is a quote from Klein's Organic Chemistry 3rd edition: Here is the bottom line: Whenever an atom possesses both a π bond and a lone pair, they will not both participate in resonance However, ...
9
votes
2answers
691 views

Validity of ionic resonance structures

What's wrong with ionic resonance structures? I asked one professor about them once and all he commented was "I've seen them too, and I think they're wrong." Another professor rejected an ionic ...
9
votes
1answer
5k views

Why is carbonic acid a weaker acid than acetic acid?

Is it because the $\ce{OH}$ group next to $\ce{COOH}$ in carbonic acid donates electron density to the $\ce{COO-}$ by resonance, making it a stronger base, compared to a weaker electron donating ...
9
votes
2answers
9k views

Inductive vs resonance effects and the acidity of phenol

A lot of people rationalize the acidity of phenol by saying that resonance is responsible for much of phenol's acidity as opposed to aliphatic alcohols. However, this image suggests that in fact the ...
9
votes
1answer
3k views

Most basic nitrogen in Adenine

I need to find the most basic site of Adenine: The $\ce{NH2}$ group and $\ce{NH}$ cant be strong base as electrons are delocalised. This leaves us with $1,7,3$. I thought that electron density on $1,...