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 will happen when 2,4,6 trinitroanisole is reacted with KOEt in HCl

I tried to do by Normal Aromatic Nucleophilic Substitution Reaction, but I think there is some other parameters or some different reactions will occur, can anyone give me a hint? A mechanism is ...
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Reactivity of heterocyclic vs. homocyclic compounds towards electrophilic aromatic substitution [closed]

I read about a specific example of the above question in a book, which said: Which one of the following compounds is more reactive towards electrophilic aromatic substitution: Pyrrole or ...
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Can a compound with indirectly bonded carbon and silicon atoms within the same aromatic system be called organosilicon compound?

Wikipedia says that organosilicon compounds are organic compounds with carbon-silicon bonds. Does the class of organosilicon compounds include compounds in which the carbon and silicon are only ...
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Hydrogen NMR aromatic Assignment [closed]

Hello all. Currently working on an NMR spectrum for the pictured molecule. In the range for the aromatic peaks I have some unexpected integrations. I am struggling to assign the possible hydrogen's ...
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Acidity order of o-nitrophenol vs. o-chlorophenol [closed]

It is given that the above statement is true. Why does o-nitrophenol, in spite of intramolecular hydrogen bonding, have a lower $\mathrm{p}K_\mathrm{a}$ than o-chlorophenol?
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Reaction of phenol with concentrated sulfuric acid

What is the product when phenol reacts with conc. $\ce{H2SO4}$ in excess? I have been told that the major product will be ortho at low temperature and para at high temperature. Why cannot it form ...
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516 views

Which biphenyl is optically active?

Which biphenyl is optically active? I know that it can never be 1. I don't think it will be 4 either as I read that it should be ortho-substituted biphenyl. So, when I look at 2 and 3, I can't ...
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62 views

Organic Chemistry - Effect of methyl substituent in Aromatic Substitution via Benzyne

The following reaction has been taken from my study material. This shows that the benzene ring is undergoing a nucleophilic aromatic substitution via benzyne mechanism (presence of a strong base like $...
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Why acidity of p-methoxybenzoic acid is more acidic than p-hydroxybenzoic acid?

I know +M effect of $\ce{OCH3}$ is more than $\ce{OH}$, but in my book (ALLEN General organic chemistry), it is given that $\mathrm{p}K_\mathrm{a}$ of para-substituted benzoic acid containing $\ce{...
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Angels Share seems bogus

What is the explanation of barreled spirits (at 62.5% ethanol) that undergo changes in concentration of ethanol. Whereas the volume after aging is typically reduced, the proof varies between low 100 ...
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What is the mechanism for trans-stilbene to stilbene dibromide?

What is the mechanism for trans-stilbene to stilbene dibromide? This is what I know: The bond between the hydrogen and bromine is broken and the bromine is given a negative charge, while the $\ce{H}$...
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How are σ+ values in Hammett Plots calculated?

First of all, I know a similar question has already been asked & answered about σ values in general, however, I am not 100 % sure this answer is correct for the following situation. So for the σ ...
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Basicity comparison between pyridine amines and other compounds

In cases 1, 2, 3, the compounds will resonate, thus giving them more stability. Firstly, I want to know whether nitrogen has a +M effect? (due to it having a lone pair of electrons?) In case 1, ...
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Cycloheptatrienyl carbanion aromaticity

Many sources including previous answers on Stack Exchange claim that it is antiaromatic. But in a different yet similar question, I have also seen people saying that a monocyclic ring with 7 or more ...
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117 views

Which of the following carbocations is more stable?

Which of the following carbocations is more stable? I know two major factors in determining carbocation stability: resonance and the number of carbon atoms neighboring the positive carbon. Does ...
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Can aniline be made with the method described in Dr Stone?

In Dr Stone, the main character makes aniline by rinsing coal tar with HCl, then mixing in ethyl acetate. See the image below. Is a method like this possible? What is occurring here?
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Electrophilic substitution of benzene with conc. HNO₃ and HNO₂

The following question was given in my FIITJEE study material: $$\ce{Benzene + \text{conc.} HNO_3 + HNO_2 ->}$$ Final product of the reaction is: , , , I started with the solution by deciding ...
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How to get the SMILES of all compounds on PubChem?

I would like to download all the compounds from ChEMBL and PubChem. For ChEMBL this is easy using their webUI. Nevertheless, for PubChem, it isn't clear how to download all the compounds on the ...
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What can we say about the dipole moment of terephthalic acid?

The dipole moment of quinol is not zero because it can exist in two different energetically favourable conformations. The weighted average is calculated to arrive a dipole moment of 1.6 D. According ...
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1answer
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Effect of chloromethyl substituent vs methyl substituent on yields of nitration

The effects of $\ce {-CH3}$ and $\ce {-CCl3}$ substituents on the product distribution of an electrophilic aromatic substitution reaction are unambiguous. The $\ce {-CH3}$ group exhibits a clear ...
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86 views

How to weight picric acid?

Picric acid is stored under a layer of water to prevent an explosion. What is the right way to measure the amount of picric acid that taken out? It is wet and containing water.
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1answer
210 views

Making aspirin without acetic anhydride

I want to make aspirin. Normal method is to react salicylic acid with acetic anhydride, but it is extremely hard to find acetic anhydride. How may I synthesize aspirin with acetic acid and salicylic ...
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What is the Criteria for a Compound Being Non-aromatic vs. Anti-aromatic?

Anti-aromatic compounds are formed with a cyclic system of planar, overlapping p orbitals containing a non-Huckel number of electrons (i.e. not 4n+2 electrons -n being a natural number-). Non-aromatic ...
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81 views

Why does coumarin predominantly exist in keto form?

By applying the logic that phenol exists in enol form rather than keto form as it attains aromatic character, why is it not the case in coumarin?
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How ethylbenzene and 1,2‐xylene are chain isomers?

How the following two structures are chain isomers? According to what I have studied in nomenclature when a compound has both cyclic and straight chain, we consider that the chain as parent chain ...
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Why is a alkyne anion more stable than a benzene anion?

I would think the benzene anion (A) is more stable b/c the compound aromatic. Yes I understand that sp hybridized carbons are more stable than sp2 for negative charges, however I thought that ...
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Does ordered mesoporous carbon (for example, CMK-3) contain aromatic rings?

I'm studying the article Synthesis of ordered mesoporous phenanthrenequinone-carbon via π-π interaction-dependent vapor pressure for rechargeable batteries, in which authors explain some properties of ...
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Why does indolizine undergo EAS on C3 and not C5 of the pyrrole ring?

In Clayden, Greeves, & Warren: Organic Chemistry Second Edition, it is said that indolizine (pyrrocoline) reacts in electrophilic aromatic substitution at the C3 of the pyrrole ring, as shown. I ...
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Can five membered ring form through Friedel-Crafts alkylation?

Our teacher told us that five membered ring can’t be formed through Friedel-Crafts alkylation but acylation is OK. Why is that? Is it because alkylation is an unfavored 5-endo-trig reaction but ...
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Why methoxy group acts similar to trifluoromethyl in nucleophilic aromatic substitution

In an online test, the following question was asked: The answer to this question was: I totally agree with the answer, as $\ce{OCH_3}$ is an EDG, hence it will tend to form meta product in this ...
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150 views

Why is p-methoxyphenol less acidic than phenol?

They have slightly different $\mathrm{p}K_\mathrm{a}$ values of 9.9 (phenol) vs 10.2 (p-methoxyphenol). They both have the same number of resonance structures too. My guess is that the resonance ...
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85 views

Why does the tautomerism of purine favor 9H-purine? [duplicate]

I tried to explain the equilibrium by comparing the basicity of different nitrogen atoms in a purine anion, but I can’t see any obvious difference. Seems like that the 9-N will be the most basic ...
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130 views

Steric Inhibition of Resonance in ortho-substituted Benzoic Acids

It is given that due to Steric Inhibition of Resonance (SIR), the acidity of ortho-substituted benzoic acid increases with respect to benzoic acid. If this is the case then the conjugate base of the ...
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Number of aromatic rings in triphenylene

My question is how to find the number of aromatic rings in triphenylene: My professor said that there are 3 aromatic rings, after which he added that the carbons of the middle rings are only ...
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Why is phloroglucinol (1,3,5-benzenetriol) not very soluble in water?

Wikipedia says that phloroglucinol (1,3,5-benzenetriol) has a solubility of 1 g/100 ml in water. This is in comparison to: phenol (hydroxybenzene) 8.3 g/100 mL catchecol (1,2-dihydroxybenzene) 43 g/...
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Can anyone please help me how do you determine kinetically the fastest product of sulphonation of $\beta$ napthol?

I was asked a question in a paper where I was asked to identify the kinetically fastest product of sulphonation of $\beta$ naphthol. Can anyone please help me how do you determine kinetically the ...
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Nucleophilicity in polar aprotic solvent (DMSO)

The strength of a nucleophile in polar aprotic solvent is proportional to its basicity. Lone pair on O- in the molecules will donate an e- pair to an atom. I'm not sure why the alkene ring in 2 makes ...
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What is non-hückel double bond of Aromaticity? [duplicate]

Chemistry of Aromaticity. What's non hückel double bond ? What are the difference between hückel and non-hückel double bond ? [ Here, in figure the green one is non hückel double bond ]
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How to make 1,1-diphenyl-1-butene from benzophenone and 1-bromopropane?

I would like to know the method of syntheses of making 1,1-diphenyl-1-butene $(\ce{C16H16})$ from benzophenone $(\ce{(C6H5)2CO},$ generally abbreviated $\ce{Ph2CO})$ and 1-bromopropane $(\ce{...
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Synthesis of phenethyl alcohol from benzene

How can I make phenethyl alcohol $(\ce{C6H5CH2CH2OH})$ from benzene? I have got information that phenethyl alcohol is made from benzene by Friedel-Crafts reaction between benzene and ethylene oxide ...
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Why do the induction effects of fluorobenzene decrease electrophilic addition reactivity, conjugation effects increase selectivity?

Fluorobenzene shows signs of both the electron withdrawing and electron donating groups on benzene. Electrophilic substitution to the ring is less reactive because the fluorine is very electronegative ...
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Will cyclopenta-2,4-dienecarbaldehyde undergo aldol condensation or cannizzaro reaction?

The following question was given in an exam.Which of the following undergo aldol condensation ? Given answer : a,b,c My answer: b,c My Logic : Cyclopenta-2,4-dienecarbaldehyde(1) on reaction with ...
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204 views

Does benzene react with steam to create an alcohol?

Benzene has a molecular formula of $\ce{C6H6},$ right? Surely it has some alkene-like properties because of the double bonds, so can it undergo a hydration reaction to create alcohol?
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What will be the product ratio if I do chlorination of p-toluic acid?

If I do chlorination of p-toluic acid using Lewis catalyst, e.g. $\ce{FeCl3},$ what will be the ratio of major product to side product? Main product shall be 3-chloro-p-toluic acid and other product ...
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138 views

How would one carboxylate CBG into its acid form, CBGA?

I have a project that would require cannabigerolic acid (CBGA) as a synthase substrate, but the only available chemical I can find is cannabigerol (CBG). CBG is the product of CBGA through ...
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99 views

How does 1-bromo-2-fluorobenzene react with lithium amalgam? [closed]

How does this organometallic reagent react with 1-bromo-2-fluorobenzene? Does it react like Grignard reagent? If the product of this reaction is then reacted with furan, what will be the final product?...
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Why is ozonolysis of benzene possible?

I was looking at a question which asked to predict the product of reductive ozonolysis of benzene using $\ce{Zn/O3/H2O2}$ and I predicted them correctly using the cleaving of the double bond shortcut ...
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221 views

Why is formyl chloride unstable while higher acyl chlorides are stable?

Source: Paula Bruice Ed. 2017 Pg.877 From this excerpt, we infer that formyl chloride is unstable. But how does that affect the reaction in any way? Is it just mentioned as a point to note or does it ...
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Is black phosphorous aromatic?

I know that graphite and boron nitride are aromatic in nature. In a similar way, can black phosphorous too exhibit aromaticity? Since it is essentially the same having 6 membered rings with lone ...
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695 views

What is quasi-aromaticity?

During my study of aromaticity, I came through this topic of quasi-aromaticity. Can you please elaborate what Quasi aromatic compounds are and how are they designated?