A conjugated ring of unsaturated bonds, lone pairs, or empty orbitals which exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone.

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Formation of 2,4-Dichlorophenol by free chlorine mediated oxidation of Triclosan

I cannot find much guidance in the literature. This is the reaction between free chlorine in water and triclosan. I understand ether cleavage and electrophilic aromatic substitution (maybe) involved. ...
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1answer
45 views

Regioselectivity of Birch reduction (electron donating groups)

Why does Birch reduction on benzene derivatives with an electron donating group happen at ortho and meta positions? When the substitute is electron withdrawing, ipso and para reduction take place ...
5
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1answer
61 views

Are phenylboranes susceptible to ipso or meta substitution?

Are phenylboranes susceptible to ipso or meta electrophilic aromatic substitution, i.e. what's the regioselectivity?
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1answer
52 views

Donation by inductive effect and withdrawal by conjugation

Is there a group that would attached to a benzene ring, donate electrons by inductive effect and withdraw them by conjugation?
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1answer
73 views

Nitrosation of benzene

How does benzene react with $\ce{NaNO2/HCl}$? Will $\ce{PhNO}$ be obtained? I read that pyridine can be produced under special conditions, but what will happen in some less exotic conditions?
3
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1answer
70 views

Are there any negatively charged electrophiles, or simply neutral and positive?

When reading up on electrophilic aromatic substitution, most resources refer to electrophiles as positively-charged species, "in general" or "mostly". What are non-positively charged electrophiles? ...
0
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1answer
39 views

Is it possible to make meta-phenol?

Normally phenols have the $\ce{OH}$ group at the 1 or 4 position. Can they be made at 2 or 3 positions, where nitro groups and $\ce{-CN}$ can attach? If not, why not?
2
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1answer
51 views

Aromaticity of cyclic ketone

By looking at the structure of the uploaded ketone, it doesn't seem that it is aromatic, but the resonance structure with C(+)-O(-) is aromatic. Is it correct to say that the ketone in the image is ...
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1answer
25 views

Converting cyclic compounds to linear compounds (possible ?)

Can one convert from cyclic convert to linear compound? Like $Cyclohexane$ $+$ $?=Hexane$ Even in High Temp and Pressure? I know it is very tough since we are going from a stable compound to a ...
2
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0answers
19 views

What sort of lab can determine PAH concentration in a soil or charcoal sample? How difficult is it to do?

Non-chemist here. I'm curious how difficult it is to determine concentration of PAH in a sample of soil or powdered charcoal, or a sample of the two mixed together. What would be involved in doing ...
2
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2answers
77 views

Why does m-cresol exist, given that -OH group is activating and should be o-, p-directing?

Why does m-cresol exist? The $\ce{-OH}$ group is a ring activating group, and hence should be o-, p- directing.
3
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2answers
115 views

Why does fusing benzene rings not produce polycyclic alkynes?

It would make sense that when the benzene rings are fused they keep their pi bonds and form a polycyclic alkyne. However this is not the case. My hypothesis is that because monocyclic alkynes at 8C ...
3
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1answer
36 views

What's the difference between Carvacrol and Thymol?

What is the difference when it comes to separating Carvacrol and Thymol on HPPLC with reverse phase - C18 column? Carvacrol elutes first, is that because it is ortho?
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64 views

Hydrogen suspended in the center of an aromatic ring and NMR

My textbook (Organic Chemistry, 2nd Ed. Hornback, Joseph) states that if a hydrogen is located near the center of an aromatic ring it will experience an (often quite sizable) upfield shift, as seen in ...
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2answers
79 views

Preparation of phenylamine/aniline

This is the procedure I carried out in class: Reduction of nitrobenzene by using tin and $HCl$ acid After the completion of the reaction, $NaOH$ added to neutralize excess acid and dissolve any ...
3
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1answer
88 views

Draw pyridine as an R Group

You know how when you carry out a reaction with many compounds, when drawing the reactions you just draw a line at a right angle to the bond with a 'R' at the end (see image)? Then you can specify ...
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3answers
501 views

what is the origin of the colour of azo dyes?

what is the origin of the colour of azo-dyes? Is it the same reason as to why transition metal complexes have colour?
5
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1answer
68 views

Steam distillation- how it actually works?

To obtain phenylamine after it is formed from the reduction of nitrobenzene with tin, we carried out steam distillation. This is what I learned in class: "During the process,steam is injected ...
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2answers
1k views

reason for the stronger acidic property of phenol than alcohol

"In phenol, pulling the $p_z$ electrons from the oxygen atom into the ring causes the hydrogen atom to be more partially positive than it is in aliphatic alcohols. This means it is much more easily ...
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2answers
384 views

Does benzene have isomers and resonance structures?

Does benzene have both isomers and resonance structures? I know that it has resonance structures because you can manipulate the position of the double bonds but what about isomers?
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115 views

Reasons for dry conditions in substituition reactions with benzene

All substitution reactions of benzene must be carried out in dry conditions with a catalyst that produces a powerful electrophile. This was a statement from my book. My question is, why must it ...
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3answers
274 views

Benzene and resonance

In my book, to explain the structure of benzene, it referred to the idea of resonance: "The idea of resonance is that actual molecule is a definite structure that is a hybrid of two theoretical ...
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1answer
1k views

Why use glacial acetic acid in bromination of anisole?

In my organic chemistry lab (next week, the experiment has not been conducted yet) we are being asked to react anisole with bromine to get 2-bromoanisole (as well as 2,4-dibromoanisole and all the ...
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2answers
68 views

Formation of 3-chloromethylbenzene VS 3-chloromethylbenzene VS 4-chloromethylbenzene

For methylbenzene (with the methyl group at position 1), is it easier for chlorine to substitute the hydrogen at position 2, 3 or 4? I was thinking somewhere along the lines of different charge ...
3
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1answer
99 views

Thermodynamic stability of benzene ring

In learned that when benzene undergoes hydrogenation, $208KJ$ of energy is given off and thus $152KJ$ less energy than what would be given off if Kekule's structure was correct. My confusion is that ...
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2answers
89 views

delocalised electrons and benzene's stability

In most high school chemistry books, it is said that the delocalised electrons in benzene makes it particularly stable. However, how does it contribute to stability? Is there any simple way of ...
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1answer
153 views

Which is better leaving group

How can I compare the leaving group ability of $Br^+$ and $Cl^+$ ions for the electrophilic substitution reactions for aromatic compounds?
3
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1answer
170 views

What does it mean by degree of aromaticity of a molecule?

This is a fundamental question, though I didn't really get the meaning/idea what does it mean by aromaticity or degree of aromaticity. Does it mean the ability of a molecule to be aromatic?
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2answers
499 views

How to distinguish between benzyl chloride and chloro benzene?

If I add $aq. \ce{KOH}$ to both of the compounds substitution takes place in the case of benzyl chloride and then if I oxidize with $\ce{KMnO4}$ I will get benzene carboxylic acid which will give ...
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1answer
90 views

Is aromaticity of the 4 aromatic amino acids affected by pH?

During a discussion of NMR, my lecturer told me to think about which amino acids contain protons in an aromatic ring, and whether any are likely to be affected by changes in pH. The 4 aromatic amino ...
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2answers
67 views

Where do things connect in EAS reactions?

If you have an aromatic ring that requires substitution of some molecule, how do you know where this molecule is supposed to substitute on the ring? In (i) and (ii) how do we select the ring and ...
5
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1answer
502 views

Resonance of benzoic acid

My book says that benzoic acid does not show resonance as the carboxylate ion and the benzene ring are not in the same plane due to steric effects. But there aren't any large group in the ortho ...
4
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2answers
707 views

Ozonolysis conditions for Benzene

What are the precise conditions under which Benzene undergoes ozonolysis? All anyone can tell me is that it undergoes ozonolysis under "vigorous" conditions. But, what vigorous conditions?
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0answers
56 views

Relative basicity of Toluidines and Nitro anilines

I have searched a lot of that in Internet. But I can't find a relevant answer. My question is about Relative basicity of different types $(O, M, P)$ toluidines and Nitro anilines or more specifically ...
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3answers
387 views

Reaction of Benzene with 2-methylpropene?

I'm studying organic chemistry at the moment and it's really confusing. What could ever happen between benzene and an alkene? and why is $\ce{H2SO4}$ there?
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333 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 -OH group is highly reaction favoring. From what I understand, this ...
4
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1answer
95 views

Is the reactivity of Benzene with an -N(R)₃⁺ group greater than its reactivity with an -NH₃⁺ group?

Both are m-directors, and Electron Withdrawing groups, but which one is more reactive? At first sight, one might think clearly $\ce{-N(R)_3^+}$ is more reactive, but when you factor in that $\ce R$ is ...
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1answer
471 views

Why are halogens ortho para directing even though deactivating?

Halogens bonded to benzene ring has three lone pairs. These three electron pairs can cause resonance in benzene ring. But, halogens are also highly electronegative and thus they have strong -I effect. ...
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1answer
104 views

How are the following aromatic?

I'm not able to understand how the following are aromatic. My first doubt is whether I have to include the lone pair of electrons while applying the Huckel Rule to these compounds? If yes, then in ...
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1answer
99 views

Will this reaction lead to diazonium chloride?

Usually $\ce{NaNO2}$ and $\ce{HCl}$ is used to make diazonium chloride. But, in this compound there are two amine groups adjacent to each other so I doubt that diazonium chloride would form. Will ...
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2answers
2k views

Why is ethanoic acid more acidic than phenol?

They say ethanoic acid is more acidic than phenol since the former can neutralize alkalis like NaOH, however, latter cannot. But if we look into the structure of ethanoate ion and phenoxide ion, the ...
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350 views

Is there any special rules for checking the aromaticity of polycyclic compounds?

This question arose in my mind because it's given in a book that pyrene is aromatic. How can it be with 16 π electrons? So, it should be actually anti-aromatic or is there any special rule for these ...
3
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1answer
2k views

Lines on inside of hexagonal shapes of structure diagrams

just a simple question from me today... I was looking at the structure of Norepinephrine for a school project and was curious about the diagrams on the Wikipedia page for it. I was wondering why ...
5
votes
2answers
277 views

aromatic nucleophillic substitution?

In aromatic nucleophilic substitution why does $\ce{F-}$ acts as the best L.G.? The reason I think is due to -I effect of fluorine being the greatest it leaves first. ((As it stabilizes messienmier ...
6
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1answer
528 views

reaction of toluene?

**Reaction of toluene at high temp gives us (o-m)toluene whereas at normal conditions of electrphillic attack it gives us (o-p) directing . Why this happens at high temp although as methyl group is ...
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2answers
221 views

Question regarding comparing different chemical's most acidic protons?

I am burning through some test prep and have a chem question that is troubling me. The questions is as follows: How would you compare the acidity of the most acidic proton in each of the following ...
4
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1answer
313 views

What is the influence of an alkyl-hydroxy group on a benzene ring?

We all know that an $\ce{NO2}$ group attached to a benzene is a deactivator, and it directs and substituents that would be adding to the meta position to the $\ce{NO2}$. For an alkyl group attached ...
3
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1answer
208 views

What is the substituent on this benzaldehyde? (MS attached)

I have no clue what the substituent may be. The molar mass of the unsubstituted benzaldehyde is 105g/mol (subtracting one H, where the substituent will be). So the substituent is around 30-33g/mol. ...
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2answers
3k views

How does Sodium Bicarbonate act as a Deodorizing agent?

I was reading this other question on the site: Deodorizing using baking powder instead of baking soda. Apparently, baking soda is used quite often as a cleaning and deodorizing agent. From what I ...
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2answers
229 views

Why aren't lower aromatic organic compounds taught?

Why aren't aromatic compounds with 3, 4 or 5 carbon atoms taught at high school level chemistry? We are instead directly taught about aromatic compounds with 6 carbons/benzene rings. Why? My core ...