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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Compare reactivity of these compunds towards nitration [closed]

Among these which has the highest reactivity to electrophilic nitration reaction:- a) Toluene, b) Nitrobenzene, c) Benzoic Acid, d) Benzene. And, if possible, shortly explain why.
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Concentrating mixtures of volatile compounds

My interest is primarily food-related here but I think this is a fairly general chemistry question. Let's say I took some liquid like lemon juice and ran it though a rotary evaporator to get just the ...
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Aromatic compound and Grignard reagent reaction

Am I correct in thinking a Grignard reagent like MeMgBr acts as a nucleophile? And would that mean it will substitute another group? So for example if you reacted it with bromobenzene, would the Br be ...
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Reducing Ketone to alcohol [closed]

If you have 1-phenylethan-1-one and reduce the Ketone side chain would you get Phenol? I know that it normally works that way in linear chains but in a book I am using they react 1-phenylethan-1-one ...
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Relation between activating properties and directing nature

Why are activating groups not always ortho-para directing and decativating groups meta directing? For example, we have: Halogens which are deactivating, but ortho-para directing. Nitro group which ...
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Reactivity of phenol and hydroquinone in electrophilic aromatic substitution

So I had a argument with my teacher about which is more reactive, phenol or hydroquinone. So he first taught us the formation of $\pi$-complex (where the $\pi$-electrons are donated to the ...
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32 views

How many π-electrons are there in 2-methylene-2H-pyran?

I thought that the structure will be aromatic and stabilised because one of the lone pairs being delocalised with the help of conjugated double bond system but still only 3 π-bonds will be present at ...
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How far does the delocalisation (resonance) effects for substituents extend for a conjugated system?

Let's say we have a conjugated system like this one: Now, the delocalisation of the benzene electrons with the nitrate system means that the ortho, and para positions on the immediate benzene ring ...
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Why does the ortho effect not work here? [closed]

The basicity order of aniline and 2,6-tertiary butyl aniline is the latter greater than the former. Why does the ortho effect not make it the other way around? Or am I missing something?
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Oxidation of toluene to benzoic acid [closed]

On Wikipedia I found the reaction of the oxidation of toluene to benzoic acid: $$\ce{5 C_6H_5CH_3 +6 KMnO_4 +9 H_2SO_4} \to \ce{5 C_6H_5COOH +14 H_2O +3 K_2SO_4 +6 MnSO_4}$$ which involves $35\, \ce{...
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Contradictions in acidity and solubility of phenol derivatives

o-Nitrophenol is less acidic in comparison to p-nitrophenol due to intramolecular hydrogen bonding. This effect also is the reason for o-nitrophenol being less soluble in water. At the same time, ...
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Solvent for reaction mixture

I'm looking for some suitable solvent for ether cleavage of Guaiacol (o-Methoxyphenol) using aluminium triiodide ($\ce{AlI3}$) with $\ce{DMSO}$. The original paper calls for using hot acetonitrile as ...
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Can someone help with this resonance form question [closed]

Struggling to understand the concept of resonance and how it provides stability to compounds, my basic understanding is that the delocalized pi electrons can move and place a negative charge on the ...
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Counting the number of conjugated pi bonds in a complex aromatic molecule

So for multiple bonds to be conjugated, they must be in an alternating double bond – single bond – double bond, etc arrangement. However, do they need to be continuous? In my textbook, they count the ...
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1answer
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Directing effect in Intramolecular Friedel Crafts Alkylation

This reaction should cause ring closure at either the $o-$ or $p-$ position relative to the methyl substituent on the ring (as methyl is an $o,p-$directing group), giving the following products: The ...
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1answer
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Carcinogenicity of polynuclear hydrocarbons and benzene rings

(1933) established that polynuclear aromatic hydrocarbons (PAHs) were carcinogenic components of pitch. ... Although less is known about their health effects than about those of PAHs, it is clear ...
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Explanation of the third ortho effect

The third ortho effect is, according to Wikipedia, the phenomenon where in a ring with a meta and an ortho-para director both meta to each other has the incoming nucleophile go ortho to the meta ...
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Stability of 4-pyridone vs 4-pyridinol

In kryptomerism assignment, there was a question to compare more stable tautomeric form between 4-pyridone (1) and 4-pyridinol (2): Answer: 4-pyridone. My friend gave two plausible reasons: $\ce{C=...
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Solvent Effects in Friedel–Crafts Reaction

While reading about the factors affecting the product of Friedel–Crafts acylation with acetyl chloride, I came across a reaction involving napthalene in two different solvents: in nitrobenzene ...
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1answer
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How to arrive at the preferred IUPAC name for 1,2-diphenylethane?

I am reading a textbook that mentions the molecule 1,2-diphenylethane, $\ce{C14H14}$. A Google search leads to PubChem, where it is mentioned that the IUPAC name for the molecule is 2-...
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Does aniline react with FeBr₃?

I have read that aniline does not undergo Friedel–Crafts reaction because it complexes with Lewis acid $\ce{AlCl3}.$ Will it also react with $\ce{FeBr3}$ during bromination (to receive a 3-bromo ...
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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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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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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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1answer
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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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283 views

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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100 views

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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2answers
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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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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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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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296 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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159 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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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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1answer
228 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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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
132 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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234 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
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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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