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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Is it possible to synthesize a benzene ring with every carbon on the ring substituted?

We recently began covering aromatic electrophillic substitution in my first year organic chemistry course, and we've been discussing the nature of certain functional groups being activating $(\ce{-OH},...
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Is the following compound stabilized by resonance due to rearrangement [closed]

Does this compound undergo rearrangement? Or is it simply stabilized by resonance?
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Confused regarding aromaticity [duplicate]

I can understand the aromaticity in the second but can't in the first structure. The second structure is aromatic since it has a continuous conjugation in the rings, but the first structure has no ...
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28 views

Adding an essential oil to WHO Handrub Formulation [closed]

I'm not a chemist, so I prefer to ask this question to some people, who definitely have knowledge in that area. WHO Handrub Formulation is available here. Ingridients: Ethanol 96%, Hydrogen peroxide ...
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1answer
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Why is o-nitroaniline not more basic than aniline?

We know from SIR effect (Steric Inhibition of Resonance) that in o-nitroaniline, the nitrogen's p-orbitals will change their plane, causing the conjugation/resonance of its lone pairs to stop. So, the ...
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How does actually negative charge travel in phenol from ortho to para to ortho? [duplicate]

When we say negative charge flows from ortho to para position, and electron density at ortho and para is more, where does electron actually stay at ortho and para? Is it at $p_\mathrm{z}$ orbital or ...
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We know that single bond,double bond structure of benzene doesn't exist then why we use it? [closed]

No explanation needed question is straight forward
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21 views

Why are Friedel Crafts reaction not possible for molecules less activated than benzene?

I know that Friedel Crafts alkylation reaction are not possible for aniline and phenol since they form complexes with Lewis Acids. But our teacher told us that Friedel Crafts reactions aren't possible ...
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24 views

Nucleophilic Aromatic substitution in 3-Bromoanisole

I came across an example in my textbook where $\ce{3-Bromoanisole}$ is reacted with $\ce{NaNH2}$ in liq. $\ce{NH3}$. My understanding is that the reaction would proceed by a Benzyne intermediate, with ...
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1answer
34 views

Why benzene takes in more delocalized electrons from its substituents even though it has six of them

Benzene has six delocalized electrons in its structure then where does it places the new electrons which it gets from other substituents like oh, etc. Why does it accepts those new ones? Please give ...
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27 views

Why do atoms stay nearer to each other even when delocalized electron moves away [closed]

When the delocalized electron moves from between two atoms to other then why yet the measurement of distance between those older two atoms is less than normal single bond.
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How to compare the acidity of this multicyclic hydrocarbon to the acidity of cyclopentadiene?

This is the question: Which one is more acidic? According to me, cyclopentadiene should have been the answer, as losing a proton would make it aromatic; whereas the first option doesn't need ...
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Why is dipole moment of 1,4 dicyano benzene and 1,4- dinitro benzene zero. Whereas that of 1,4 - dihydroxy benzene is not zero [duplicate]

I've been taught that dipole moment in para position is zero, if the group attached has only one electronegative atom. This doesn't apply to 1,4 dinitro benzene or 1,4 dihydroxy benzene. Have I learnt ...
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1answer
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Assigning Peaks and Determining J Values for Mata-Disubstituted Benzene

I need to determine as many J values as I can for 3-methoxybenzaldehyde. The peaks overlap a lot, and I don't see the expected ddd or dt pattern that I would expect for the hydrogen on carbon 6. The ...
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1answer
88 views

Major product of mononitration of 3-methylphenol

From NCERT Class Chemistry Part 2: Example 11.5 Write the structures of the major products expected from the following reactions: (a) Mononitration of 3-methylphenol (b) Dinitration of ...
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Steric inhibition of resonance in substituted benzoic acid

Why does attaching an $\ce{-NO2}$ group at the ortho position of benzoic acid cause $\ce{-COOH}$ to become perpendicular to the plane of the benzene ring? Why doesn't the nitro group get pushed out ...
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Trimethylsilyl vs tert-butyl as activating substituent of benzene

Would trimethylsilane as a benzene substituent have an activating effect relative to tert-butyl for electrophilic substitution reactions?
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1answer
25 views

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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23 views

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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35 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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1answer
44 views

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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62 views

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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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
45 views

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
102 views

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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1answer
174 views

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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1answer
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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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3answers
227 views

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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157 views

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
118 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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2answers
468 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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1answer
135 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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85 views

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
212 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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309 views

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
770 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
54 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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