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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The mechanism of separating AlCl3 [on hold]

For this question I have gotten to: I know I am supposed to separate the $\ce{AlCl3}$ through aqueous work up, but I am not sure what the mechanism is. The resulting answer is the enol/keto form + $\...
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Major Organic Product of pheylpropene and diazomethane? [on hold]

What is the major organic product synthesized from phenylpropene and diazomethane? I get that N2 from the diazomethane is going to be the leaving group correct and it forms the carbene :CH2 correct? ...
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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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1answer
210 views

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
25 views

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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78 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
92 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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25 views

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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69 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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79 views

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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1answer
26 views

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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1answer
81 views

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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1answer
54 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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1answer
80 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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1answer
96 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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1answer
98 views

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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3answers
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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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1answer
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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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48 views

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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1answer
190 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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1answer
48 views

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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1answer
130 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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1answer
71 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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1answer
162 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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1answer
555 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?
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Why is the trimethylammonium group a stronger electron withdrawing group than the nitro group?

I was working on a question that basically boils down to deciding whether the nitro group ($\ce{-NO2}$) or the trimethylammonium group ($\ce{-N+(CH3)3}$) on a benzene ring, is a stronger electron ...
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1answer
80 views

Aromaticity of conjugated cyclic ketones [closed]

Consider the following compounds: Cyclopenta-2,4-dien-1-one Cyclopent-2-en-1-one In both compounds, I can visualize a resonating structure in which the ring follows Huckel's rules by: The $\ce{C=O}$...
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39 views

Number of hyperconjugative structures in aromatic systems

I know that to find the number of hyperconjugative structures in aliphatic systems we use the formula $a + 1$ (where $a$ is the number of α-hydrogens in that compound) However, my teacher answered ...
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1answer
64 views

Consequences of ortho effect on resonance

Consider any carboxylic acid with any group at ortho position. According to ortho effect, the resonance of the $\ce{C=O}$ with the ring is inhibited. Is this resonance entirely lost? Or some little ...
5
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3answers
984 views

Why does the -OH group in β-naphthol direct the incoming diazonium salt towards the ortho position? [duplicate]

In the following reactions, the major product W is I was doing this question which asks me the product of a diazotisation coupling reaction between diazonium chloride and β-naphthol. I know ...
5
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1answer
156 views

Why is porphyrin aromatic?

I was asked which of the following were aromatic: My understanding of aromatic nature is, that the molecule must be cyclic, planar, every atom in the ring must be sp2-hybridized and the molecule must ...
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45 views

Identifying weaker base

Can you tell me the reason behind the answer to this: Which is the weaker base? (a) o-cresol; (b) Trifluoro-o-cresol. Answer: (b) trifluoro-o-cresol. I'm not a student in any institution. So ...
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85 views

Does acetophenone show haloform reaction?

Although acetophenone is a methyl ketone, as it is aromatic, it is immiscible in H2O so the last step in the haloform reaction should not occur? I couldn't find any source regarding the haloform ...
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Can benzene undergo Diels–Alder reactions?

I was reading about the Diels–Alder reaction and wondered that since benzene also consists of two conjugated double bonds, then should it also undergo Diels–Alder reactions? If not, then why not?
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Aromaticity of Tropone [duplicate]

When we are determining if a given compound is aromatic using Hückel's rule, we count the number of delocalized $\pi$ electrons. In tropone for example, if I wanted to count the number of delocalized ...
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62 views

Organic conversion involving Grignard reagent and alkyl group with a carbonyl carbon on an benzene ring

I have been asked to synthesize the organic compound shown below using the following reagents and solvents. $\ce{Mg, Zn, Hg, FeBr3, AlCl3, Br2, LiAlH4, KMnO4}$, dil. $\ce{H2SO4}$, conc. $\ce{NH3}$, ...
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1answer
284 views

Nitrobenzene - Aromatic Substitution Reactions

Which EAS (electrophilic aromatic substitution) reactions does nitrobenzene show? We know that nitrobenzene is particularly deactivated towards most such reactions, as the nitro group is strongly ...
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1answer
53 views

Why is a compound that is more stable gives out less energy upon reaction? [closed]

I am having trouble relating stability with energy released. For example, I am looking at a statement regarding Benzene that says, since delocalised electron model of Benzene is more stable than the ...