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.

learn more… | top users | synonyms (1)

2
votes
1answer
61 views

Nitrosation of benzene

How does benzene react with NaNO2/HCl? Will PhNO be obtained? I read that pyridine can be produced under special conditions, but what will happen in some less exotic conditions?
3
votes
1answer
57 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
votes
1answer
38 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
votes
1answer
48 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 ...
1
vote
1answer
24 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
votes
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
votes
2answers
70 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
votes
2answers
105 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
votes
1answer
32 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?
0
votes
2answers
61 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 ...
1
vote
2answers
70 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
votes
1answer
79 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 ...
2
votes
3answers
475 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
votes
1answer
67 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 ...
4
votes
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 ...
4
votes
2answers
306 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?
1
vote
3answers
111 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 ...
3
votes
3answers
265 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 ...
2
votes
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 ...
2
votes
2answers
62 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
votes
1answer
93 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 ...
1
vote
2answers
83 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 ...
0
votes
1answer
147 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
votes
1answer
166 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?
2
votes
2answers
449 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 ...
2
votes
1answer
87 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 ...
0
votes
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
votes
1answer
456 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
votes
2answers
673 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?
0
votes
0answers
51 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 ...
0
votes
3answers
369 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?
2
votes
0answers
317 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 ...
3
votes
1answer
87 views

Is the reactivity of Benzene with an $-N(R)_3^+$ group greater than its reactivity with an $-NH_3^+$ 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 ...
0
votes
1answer
436 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. ...
2
votes
1answer
85 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 ...
2
votes
1answer
97 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 ...
1
vote
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 ...
7
votes
2answers
317 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
votes
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
249 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
votes
1answer
520 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 ...
2
votes
2answers
217 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
votes
1answer
295 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
votes
1answer
205 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. ...
2
votes
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 ...
6
votes
2answers
219 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 ...
3
votes
2answers
117 views

Help Identifying Chemicals

I was trying to isolate elemental bismuth from pepto bismol (bismuth subsalicylate) using the process seen here but after I added the HCl, instead of getting a pink foamy substance I got a white ...
2
votes
1answer
310 views

How do you Benzylate (add a benzene group to) cyclic compounds?

How do you add a benzene group to cyclic compounds like piperidine, piperazine and phenyl derivatives? Piperidine Piperazine
6
votes
1answer
476 views

What is the name of the “primary” carbon in a benzene derivative?

If we have a benzene with a single substituent, such as chlorobenzene, what do we call the carbon atom to which the group is attached? I'm familiar with the ortho- meta- para- nomenclature, but the ...
17
votes
5answers
196 views

Why are smoke odors persistent in fabrics?

Obviously smoke is very complex, but apparently phenol compounds are the main components of wood smoke that produce the characteristic odor. (One of more significant of these compounds seems to be ...