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.

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What is the name of the molecule?

I could not find the appropriate name for the molecule according to the rules of nomenclature, I would be happy for help
Ofek Saragosty's user avatar
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When is an electrophilic aromatic substitution reversible?

Hi Chemistry StackExchange! I'm currently in Organic Chemistry II, and we're learning about electrophilic aromatic substitutions. I understand the mechanism and various reactions you can use, but I ...
Samuel Lee's user avatar
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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
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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
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1 answer
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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
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1 answer
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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
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1 answer
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Is This compound stable at room temperature?

This compound is planar conjugated and has 8 pi electrons on its periphery so it can be anti aromatic but if we polarize the pi bond at the bottom of the right ring the left ring will become aromatic ...
shur's user avatar
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Why are halogens considered as +M group in organic reactions but -I group in some other cases?

Why are halogens (more specifically Bromine and Chlorine) considered as +M(mesomeric effect) group in electrophilic substitution reactions of aromatic compounds ( and thereby, ortho and para directing ...
Ars's user avatar
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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-xi's user avatar
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Can electrophiles be non-polar? [closed]

I ask because I came across this question: Isn't SO3 non-polar as the dipoles would cancel due to its tigonal planar structure and therefore it couldn't act as an electrophile? Would an ...
nmrislife's user avatar
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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
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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
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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
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2 answers
125 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, ...
Bharat Karri's user avatar
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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 Kumar's user avatar
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1 answer
297 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
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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
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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
1 vote
1 answer
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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
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1 answer
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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
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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
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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
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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
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2 answers
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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
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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
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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
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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
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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
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1 vote
1 answer
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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
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2 answers
158 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
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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
86 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
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0 answers
35 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
306 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
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1 answer
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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
97 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
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-1 votes
1 answer
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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
104 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
2 votes
1 answer
198 views

Which hydrogen in 3-ethynyltoluene is the most acidic?

Arrange the three types of hydrogens in 1‐ethynyl‐3‐methylbenzene in the order from the most acidic to the least. From my understanding, the hydrogen on methyl would be the most acidic as the ...
Satya's user avatar
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-3 votes
1 answer
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How is SO3H added to a benzene ring with two substituents present

If a benzene ring with an isopropyl group in the first position and bromine in the 3rd position was mixed with SO3 and H2SO4, where would the SO3H attach? Since Br is a deactivating agent that directs ...
Kevin's user avatar
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-4 votes
1 answer
157 views

Planarity of rings [closed]

Can a 7 or less than 7 membered homocyclic ring with unsaturated C atoms and fully conjugated system, lose planarity? The smallest homocyclic non-planar ring that I know is cyclooctatetraene which is ...
Shubhayu Basak's user avatar
-2 votes
1 answer
82 views

Acidic strength order among hydroxytetralones [closed]

I can understand in 1 the conjugate base has more stability for better resonance but in 2 and 3 the effect of resonance cannot be considered. How can we compare the inductive effect in such case?
Shubhayu Basak's user avatar
4 votes
0 answers
60 views

Retrosynthesis of 1-(3-chloro-5-nitrophenyl)-2,2-dimethylpropan-1-one

I was tasked with figuring out the order of attaching the functional groups to a benzene ring for the synthesis of 1-(3-chloro-5-nitrophenyl)-2,2-dimethylpropan-1-one: I propose the following order: ...
Zack Eichenbaum's user avatar
-4 votes
1 answer
73 views

Acidity of Benzenepropanenitrile [closed]

Which is the more acidic hydrogen in the parent chain of this compound? I am confused while considering the various electronic effects.
Pupz's user avatar
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0 votes
0 answers
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How can I make a polyurethane formulae more adhesive?

For a project I'm working on, how can I make polyurethane more adhesive and able to stick to surfaces more effectively, not necessarily super-glue like but just stickier properties. What other ...
Poppy's user avatar
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1 vote
0 answers
49 views

General safety of aromatic vs. aliphatic hydrocarbon solvents

I am not a chemist and I could use some help from those who know. I am wondering about some properties of hydrocarbon solvents that are commonly used for degreasing in other fields. It seems many of ...
Tim_0's user avatar
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2 votes
2 answers
436 views

What compound was drawn on this sidewalk?

A friend found this in the sidewalk of Kent town of Canterbury: What compound is this, and why would its picture be there?
Aleister Tanek Javas Mraz's user avatar
-1 votes
1 answer
399 views

what happens if benzene reacts with Cl2 in presence of FeBr3?

we know that halogenation of benzene adds a halogen to benzene in presence of a strong electrophile. but what if we use chlorine as a halogen but use an electrophile made out of a different halogen, ...
fahabccs's user avatar
-1 votes
1 answer
255 views

What does chemically happen to rubber when it soaks in mineral spirits type 1? [closed]

Mineral spirits(mineral turpentine)type 1 is a mixture of aliphatic and alicyclic hydrocarbons with a maximum content of 25% aromatics and less than 0.1% benzene and all kind of impurities. I have ...
xchcui's user avatar
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-5 votes
1 answer
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Resonance structures of benzene [closed]

Does benzene have more than two resonance structures? I draw a third resonance structure keeping 1 bond fixed and rotating other two bonds I get opposite charges on two para position. Is this ...
Sunny Vishwakarma's user avatar

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