Skip to main content

Questions tagged [aromatic-compounds]

For questions about the properties and reactions of aromatic compounds. This tag should also be applied to antiaromatic compounds. This tag should not be applied to general questions about resonance, use the [resonance] tag instead.

Filter by
Sorted by
Tagged with
0 votes
0 answers
29 views

Why nitration of aniline carried out after acetylation give ortho and para major products?

I was reading about the meta directing nature of anilinium cations and the answer mentioned that these reactions are usually carried out with 90-98% sulphuric acid. At these concentrations I would ...
mechanist's user avatar
4 votes
0 answers
38 views

Mechanism of Cu Catalyzed reaction between Benzoic acid with DMF

I'm looking for the mechanism of this reaction that I have stumbled upon. It is believed to be a radical reaction and I can kinda see that but I'm not convinced that I can understand all of the steps, ...
GabrielAlx's user avatar
-3 votes
0 answers
40 views

What is the chemical cause of 'wet-dog' smell? Is there a difference if the surface of smell origin is organic(a literally wet dog) or inorganic? [closed]

Organic Surface Wet-Dog: Literal wet-dog smell on a wet dog is of microbiological origin. What are the products of microbiological metabolism that are responsible for wet-dog? Is it a wide variety of ...
JJ123's user avatar
  • 67
-3 votes
1 answer
33 views

ease of dehydration [closed]

ease of dehydration for the following alcohols is? I understand the most easiest would be for III, but shouldn't it be easier for I than for II? because II forms an anti aromatic compound? But the ...
user145228's user avatar
4 votes
2 answers
551 views

I left scented candles in a polypropylene container. How do I remove the smell?

I left scented candles in a polypropylene container, for many weeks. How do I remove the smell? I've tried: Hand wash with Dish Soap (a few times) Hand wipe with Isopropyl Alcohol (a few times) ...
JJ123's user avatar
  • 67
-2 votes
1 answer
50 views

Why is o used for hydroxy groups in IUPAC naming instead of saying 2-hydroxy [closed]

For this question, i marked compound II correct as 2-methylbenzaldehyde and got the question correct, but for compound I, i marked it wrong and suggested the name to be 2-hydroxybenzaldehyde. I got ...
Snehal Bhadani's user avatar
1 vote
1 answer
96 views

1-Bromo-4-tert-butylbenzene reaction with NaNH2 [closed]

I'm struggling to grasp how the reaction would turn out. Could you help? My idea was that the bromide atom will get replaced by the amino group of $\ce{NaNH2}$, but when I google, I read that $\ce{...
wengen's user avatar
  • 257
1 vote
0 answers
13 views

DIY method for regenerating activated carbon in air filters

I am interested in regenerating activated carbon used in general house-hold air filters. I am looking for a sufficiently efficient and easy method to do this in home setting. A little tinkering in a ...
Imsa's user avatar
  • 11
-1 votes
2 answers
102 views

Which one has a greater dipole moment: benzamide or benzoic acid?

My guess is that, since the relative electronegativities are similar, therefore the difference would arise only due to magnitudes of difference in electronegativities. And hence the strength should be ...
Gajraj Singh's user avatar
4 votes
2 answers
269 views

Is there a symbol or representation for tolyl groups as there is for the phenyl group?

Is there a symbol or representation for tolyl groups as there is for the phenyl group? Phenyl group is often represented by "Ph" when for a matter of space you can not draw the entire ...
Eduardo L. Gutiérrez's user avatar
-2 votes
1 answer
65 views

Why do halobenzenes not give Birch reduction?

I was studying Birch reduction and my book says halobenzene and phenol do not give Birch reduction. I want to know why these two type of compounds do not give Birch reduction. I also want to know if ...
Abhijeet Singh's user avatar
-1 votes
0 answers
35 views

Catalytic hydrogenation of Benzene

Why is Benzene not hydrogenated when a side group is catalytically hydrogenated? Some books say that the Benzene ring is also hydrogenated, others say the opposite.
Jonah's user avatar
  • 17
1 vote
1 answer
117 views

How does the following cyclization reaction work?

The following is a reaction from a school provided lab manual. However, I am unable to find anything similar to the cyclization reaction taking place. All of the reactions I have found online make use ...
Marethyu's user avatar
0 votes
0 answers
25 views

Is this fused ring molecule aromatic? [duplicate]

In my notes, I can see that it is listed as anti-aromatic because of the 16 electron ring current that would be formed on the periphery of the entire molecule were the right benzene ring drawn in the ...
Bytes Per Second's user avatar
0 votes
1 answer
42 views

Non-catalysed exhaust gas

I'm writing up an academic paper (medical) on in-car exhaust levels and their effect on health. So as to ensure detection of leak-points that are located further along than the catalytic converter, in ...
Medical_researcher's user avatar
2 votes
0 answers
105 views

Removing DCC and its by-product from Steglich Esterfication

In my small research, I want to synthesize 3 alkyl gallates (ethyl gallate, butyl gallate, and hexyl gallate), and here's my overall reaction using Steglich esterification): However, from reading ...
Jonathan's user avatar
  • 117
0 votes
1 answer
129 views

Is acetophenone a saturated compound?

In many of the sites in online, acetophenone is mentioned as an unsaturated compound because of the presence of C=C bond in the phenyl group. But, many of my teachers say that it is a saturated ...
Vinay5101's user avatar
1 vote
0 answers
70 views

Is 2,5-dimethylidenecyclopent-3-en-1-ide aromatic?

Ah yes, the age-old question. I understand from previous posts on this website that aromaticity can't be defined with using four rules. But I was curious about this particular anion: It certainly ...
Samuel Lee's user avatar
0 votes
1 answer
121 views

Aromaticity of a fused ring compound

On a test, I marked this as aromatic, but the answer key says it's wrong. My thought process: It has 10pi electrons, so it follows Huckel's rule All carbons are sp2 hybridized It is cyclic Every atom ...
nidhishtyagi's user avatar
1 vote
1 answer
239 views

Can a carbocation ever be more stable than a neutral molecule?

The question is about finding the most stable molecule or species. Now my thought process was that cyclopropenylidene(1) was a carbene so would be unstable even though it is aromatic. Cyclopenta-1,3-...
mechanist's user avatar
5 votes
1 answer
170 views

How is nitrogen the most powerful electron donor in aromatic rings?

In Clayden, page 735, Aromatic Heterocycles 1:Reactions: The other simple five-membered heterocycles are furan, with an oxygen atom instead of nitrogen, and thiophene, with a sulfur atom. They also ...
zxen's user avatar
  • 105
1 vote
0 answers
79 views

Why is the melting point of meta-diiodobenzene higher than that of ortho-diiodobenzene?

I'm currently trying to reason for as why the melting point of meta-diiodobenzene higher than that of ortho-diiodobenzene and I'm unsure of what to say. I understand the para isomer has the highest ...
bigmannus's user avatar
5 votes
0 answers
115 views

Electrolytic reduction of nitrobenzene in differing media

In my lecture notes it is given that in a weakly acidic medium, nitrobenzene on electrolytic reduction gives aniline, which makes sense to me because there is ample H+ in the medium to continue adding ...
Gaurav Sai Maddipati's user avatar
2 votes
1 answer
87 views

Does tropylium chloride exist in ionic form or does it exist as a covalent molecule?

My teacher taught me that in tropylium chloride, the chlorine atom posses negative charge to make the ring aromatic. I wonder that then will this compound will exist in ionic form due to very high ...
Madhav Mittal's user avatar
0 votes
2 answers
147 views

Aromaticity of chlorobenzene [duplicate]

Hückel's rule predicts that; a planar ring molecule will have aromatic properties if it has 4n+2 π electrons in conjugation. If 4n π electrons are in cyclic conjugation, then it is anti-aromatic. So, ...
BK01's user avatar
  • 55
1 vote
0 answers
62 views

How does Tollen’s reagent reacts with hydroxylamine?

How does the Tollens' reagent react with hydroxyl amines? For example, let's consider phenylhydroxylamine $\ce{Ph-NH-OH}$ reaction with Tollens' reagent. First it yields $\ce{Ph-N=O}$ and on further ...
Aditya's user avatar
  • 35
4 votes
1 answer
299 views

Nomenclature of C6H5CO-O-NH2

How to name the following compound using IUPAC nomenclature? I found benzyl carbamate to be very close to my structure, but couldn't find an exact compound online which matches mine.
kzmom's user avatar
  • 51
1 vote
0 answers
59 views

Rule for which heterocycles are stable?

In medicinal chemistry, is there a rule for which aromatic heterocycles are stable? I've heard that heterocycles with 3+ adjacent nitrogens for example are unstable. However looking in ChEMBL at the ...
Alex I's user avatar
  • 283
0 votes
0 answers
75 views

Steglich Esterification in Alkyl Gallates

Based on my research (reading some articles), some alkyl gallate syntheses used Steglich esterification instead of the usual esterification (Fischer esterification). The reason why Steglich ...
Jonathan's user avatar
  • 117
0 votes
0 answers
57 views

Kekulé's description of benzene [closed]

“I was sitting writing at my textbook, but the work did not progress; my thoughts were elsewhere. I turned my chair to the fire, and dozed. Again the atoms were gamboling before my eyes. This time the ...
Harikrishnan M's user avatar
2 votes
1 answer
147 views

Why can't picric acid be made more acidic by adding nitro groups at the meta positions?

I understand that picric acid is acidic because of the $\ce{-NO2}$ electron withdrawing group, but why can't we add more of those on the meta positions to make it more acidic? Is it because that $\ce{-...
User10001010001000's user avatar
0 votes
1 answer
111 views

Friedel-Crafts alkylation of fluorochloropropane

Consider benzene reacting with 1-chloro-3-fluoropropane, with $\ce{AlCl3}$ as the Lewis acid. My question is, is this reaction feasible? If so, what is the product formed and do cationic ...
Srish Dutta's user avatar
0 votes
0 answers
28 views

Is -NR3+ really meta directing? [duplicate]

For electrophilic aromatic substitution, it is said that -NR3+ is meta directing, but since it only shows electron withdrawing inductive effect and inductive effect decreases with distance so it must ...
Garv Chaudha's user avatar
1 vote
0 answers
113 views

What's this reaction converting 9,10-dihydroanthracene into anthracene

I have no idea what this reaction converting 9,10-dihydroanthracene into anthracene is. Could someone help me with the name of the reaction/ or explain the mechanism of the formation of the product? 9,...
CarnotEngine's user avatar
1 vote
1 answer
94 views

H-NMR Analysis of C15H24O

I was able to figure out that the structure of this compound was a benzene ring with 2 equivalent trimethyl groups to give the 18H singlet. Another non-equivalent methyl group to give the 3H singlet. ...
Mason's user avatar
  • 11
0 votes
2 answers
229 views

Understanding Hybridisation in Cyclic Compounds

I had a doubt while solving this problem. At first glance of these compounds, I felt that all of them have sp3 hybridisation (for nitrogen), since all of them had 3 bonded pairs and 1 lone pair around ...
Dr Watson's user avatar
8 votes
1 answer
732 views

Is tropylium cyclopentadienide possible?

Has this ever been tried? The respective aromatic ions are readily accessible, e. g., in the form of sodium cyclopentadienide and tropylium bromide. It shouldn't be hard to just combine these two ...
H. Weirauch's user avatar
3 votes
0 answers
52 views

Pyrazole iodination

I'm now working on synthesizing 4-Iodo-1,3-dimethyl-1H-pyrazole starting from 1,3-Dimethylpyrazole, iodine, and hydrogen peroxide. I think the mechanism is just a simple aromatic nucleophilic ...
Hanjin Choi's user avatar
0 votes
0 answers
69 views

What's the current of an aromatic ring?

Aromatic molecules like benzene have a ring current, created by the movement of electrons around the ring. This is most visible during proton NMR, when the magnetic field of the ring current opposes ...
WaveInPlace's user avatar
1 vote
0 answers
91 views

Does heating 3-phenylpropionic acid decarboxylate it?

Here, when P is reacted with $\ce{SOCl2}$ and then NaCN to give 3-phenylpropionitrile and then hydrolysed to give 3-phenylpropionic acid. Why shouldn't it further decarboxylate and dehydrogenate to ...
Fighter's user avatar
  • 21
1 vote
1 answer
404 views

Do Benzyl Halides undergo SN1 or SN2 with Ammonia?

Does this reaction show SN1 or SN2 mechanism? Our teacher told that it shows SN2. But wouldn't the stability of benzylic carbocation mean an inclination towards SN1?
Arghya Shubhshiv's user avatar
0 votes
2 answers
187 views

Does nitration of phenol with nitric acid yields 2,6-dinitrophenol?

I've learnt that the $\ce{OH}$ group is 2- and 4-directing, but this has caused some confusion. If $\ce{HNO3}$ reacts with phenol, would there be any 2,6-dinitrophenol produced? I know that the first ...
nav op's user avatar
  • 131
1 vote
0 answers
124 views

Resazurin not turning pink

I want to add resazurin to my media as an anaerobic indicator. To my understanding, the resazurin is blue when first added to the media, then turns pink after autoclaving, and finally it turns ...
David Madrigal Trejo's user avatar
3 votes
0 answers
87 views

How does the synthesis of [18]annulene proceed stepwise?

Finding good literature on the synthesis of [18]annulene is challenging, as most sources are well old and quite archaic, so I was hoping some explanation in regard to the mechanism of synthesis. My ...
Evamentality's user avatar
0 votes
0 answers
37 views

Substituent effect on Aromatic compound (Nucleophilic addition)

The reaction shows a nucleophilic addition: The reaction on the left is faster because methoxy substituent is on the meta position of the ring, while the right side reaction is located on the para ...
user307640's user avatar
3 votes
1 answer
349 views

Non Aromaticty due to Cross Conjugated Systems

I was going through this site looking for some answer on aromatic character, definition and other ways of judging an aromatic compound, when is tumbled upon this question: Are p‐xylylene and fulvene ...
Ham Lemon's user avatar
  • 169
-2 votes
1 answer
95 views

Stability of benzyl free radical hyperconjugated with a methyl group

In this picture, which one is more stable? My teacher says the second one as it has 4 alpha-Hydrogen whereas in the first picture the free-radical carbon has only 1 alpha-Hydrogen. That's why second ...
Isteak Ahamed Imon's user avatar
4 votes
0 answers
101 views

What is the driving force of Bartoli indole synthesis?

The Bartoli indole synthesis mechanism begins with a series of attacks on the nitroarene regent by the Grignard reagents. But the atom $\ce{O}$ in $\ce{-NO2}$ should be negative, and Grignard reagent ...
HasturQ's user avatar
  • 49
-1 votes
1 answer
402 views

Why is the melting point of 4-bromoacetanilide so high? Does it have any reason to do with the chemical structure, or the para aspect?

We used melting point to determine the type of bromoacetanilide, and it was closest to 4-bromoacetanilide. How can I explain why the melting point was what it is?
user132308's user avatar
1 vote
0 answers
121 views

Will this reaction apparatus work (refluxing under inert atmosphere)

The nitrogen flow comes from the right side, directly into the flask. Then will go up the condenser and through the bubbler to release pressure. I am worried that my solvent that evaporates when ...
Mattias Weiland's user avatar

1
2 3 4 5
20