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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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 ...
7
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1
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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 ...
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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 ...
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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 ...
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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 ...
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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?
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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 ...
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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 ...
3
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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 ...
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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 ...
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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 ...
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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 ...
4
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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 ...
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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?
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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 ...
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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 ...
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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 ...
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Planarity of rings [closed]
Can a 7 or less than 7 membered homocyclic ring with unsaturated C atoms and fully conjugated system, loose planarity ? the smallest homocyclic non planar ring that I know is Cyclo-Octatetra-ene which ...
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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?
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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:
...
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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.
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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 ...
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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 ...
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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?
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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, ...
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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 ...
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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 ...
6
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2
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Do aromatic canonical structures make the overall compound aromatic?
Here, the compound itself appears to be non-aromatic, but if the double bond between the ring and the oxygen is broken into a single bond, with oxygen pulling the electrons towards itself and ...
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Why are the vapor pressure of toluene and benzene different?
We learnt to apply Raoult's law for the ideal solutions. When the questions are asked, they tell that the intermolecular forces of toluene and benzene are equal. But in the same question, they provide ...
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Where is the aromatic ring in the pentacene molecule?
I have the following problem: I am given the coordinates of the atoms of a pentacene molecule ($\ce{C22H14}$), and I would like to find the ring where the aromatic bond is located. Is this possible? ...
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Are aromatic methoxy-groups more para-directing than aromatic TBDPS-ethers?
I'm searching a comprehensive explanation for the following issue. Even though I knew before, that a regioselective bromination of compound 1 could be problematic, I wondered that the undesired 6-...
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Benzene Identification in a liquid? [closed]
how can we identify the presence of benzene in a liquid? How to find the percentage of benzene in a liquid? Are there any feasible tests that could be done to find it?
Honestly, all we have is a ...
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Are all resonance forms of pyracyclene equivalent?
This is pyracyclene:
If I’m correct, pyracyclene has four resonance forms (double carbon bonds shown in red):
Now my problem is estimating the dominance of each form. Are they equal or is there one ...
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Solubility of pyridine and pyrrole in water
Pyridine and pyrrole are two of the first aromatic heterocycles encountered in organic chemistry. Recently, I was surprised to find that their solubility properties are vastly different.
The website ...
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What is the hybridization of the carbon atom in cyclopropenyl carbocation?
The hybridization of the carbocation in the cyclopropenyl carbocation (which is aromatic) should be sp as it as the + and also is in a ring. But the carbocation has a sp2 hybridization, why?
For ...
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Why β-proton of 7-hydroxycoumarin is more deshielded than α-proton?
Umbelliferone (or 7-hydroxycoumarin) has the following signals in the 1H-NMR spectrum:
I don't know if my question makes sense but why the H3 is more shielded than H4 in the α,β-unsaturated lactone? ...
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When can lone pairs participate in aromaticity? [closed]
Basically, I'm confused on when lone pairs can participate in aromaticity, by the Huckel definition. Why can lone pairs on a carboanion be aromatic? I thought carboanions are sp3 hybridized, and the ...
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1,1-Diphenylethylene subproduct/impurity
I'm working with 1,1-diphenylethylene and I've observed that, if left at room temperature in the air atmosphere, a white insoluble powder forms. I'm unable so dissolve this powder in every solvent ...
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Polymer purification by reprecipitation troubleshooting
I am synthesizing new polymer that has not been reported before. The structure of the polymer is based on indacenodithienothiophene unit and thiophene. I used Stille polymerization. As monomers, I ...
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How does aromaticity play out in carbon nanohoops?
Within the family of carbon phanes,one that has caught my attention is cycloparaphenylene. Considering that in practice it is just a segmented piece of a carbon nanotube, is must be aromatic in nature....
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Oxidation of toluene, ethylbenzene and styrene with potassium permanganate in acidic medium
While I was studying my organic chemistry textbook, I came across the following reactions that need more clarifications:
Oxidation of toluene (1) is the only reaction from the textbook, and I ...
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comparing basic strength of toluidine isomers [duplicate]
I would like to compare the basicity of ortho and para isomers of toluidine.After comparing the pKb values online the order of basic strength is:
p—toluidine> m—toluidine> aniline> o—...
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What will be the product of 1 eqv Benzene reacts with 1eqv H2? [closed]
how equivalent concept is applied in the above problem, Kindly help me out with the answer and proper explanation.
As, I am getting confused in mole concept and equivalent concept here.
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Azulene Conjugation?
I'm trying to figure out how azulene is an aromatic compound; I understand it is cyclic, flat, and follows Huckel's rule, but I don't understand how it is conjugated.
I have circled what I believe to ...
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Retrosynthesis of (2E)-1-(2,4-dimethylphenyl)-3-(thiophen-2-yl)prop-2-en-1-one
I am struggling to find a way to disconnect this molecule and I am unsure of the order:
First, I was thinking of disconnecting the C=C of the α,β-unsaturated carbonyl. Then for the thiophene group ...
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What does heating Pd do in this organic reaction? [closed]
I thought the answer to this question is 7 but the answer is 8. What happens in last step?
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Purpose of "1H" in naming of substituted heterocyclic compouns [duplicate]
I had a curious thought about the following molecule's name:
For such a simple molecule it seemed awfully complicated. From what I gathered, the "[c][1,2]oxaborinin-1-ol" stems from the ...
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Is the Glaser coupling reaction possible with metal alkyne complexes?
As the Glaser coupling reaction is usually done with terminal alkynes with the hydrogen being straight, I wonder if the same reaction can occur in terminal alkynes connected to the backbone of a metal ...
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Smarts string for querying two N substitutions at any place along bicyclic ring
I'm a newbie to SMARTs string representation and have been stuck on generating the structure that I want. I have a pattern of chemical scaffold of interest which I'd use as a query to screen a library....
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What is the effect of NaNO2/HCl at 0-5° C on Nitro group?
In this particular reaction firstly $\ce{NaNO2/HCl}$ at $\pu{0-5°C}$ was taken and after that $\ce{H2/Ni}$ .
But what I doubt is, was there any role of $\ce{NaNO2/HCl}$ at $\pu{0-5°C}$ ?
Since only ...
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