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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Electrophilic Aromatic Substitution on meta-xylene

During EAS on meta-xylene, is the product where the electrophile is added to the ortho position relative to both the methyl formed in good yield, since the methyl groups are bulky wouldn't there be ...
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120 views

Complete mechanism of benzotriazole synthesis from o-phenylenediamine

Does my suggested mechanism for benzotriazole synthesis look correct? Are the arrows for the cyclization in the right place? Chemdoodle (which I drew this with) makes the curly arrows look a bit weird....
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Why is selenophene aromatic?

According to Wikipedia, The selenophene molecule is flat and aromatic. Being aromatic, it undergoes electrophilic substitution reactions at the 2- or 2,5-positions. These reactions are slower than ...
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Electrophilic substitution on disubstituted benzene, when deactivating groups are at para

As far as I have been able to understand this, the sites of electrophilic substitution are majorly decided on basis of the fact that "Where the electron density is more, electrophilic ...
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When does an aromatic ether break its bonds?

I was reading some reactions of ethers and I came across Zeisel determination. Later that day, I was asked to determine the products of the reaction : And I made the product: This reaction is ...
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1answer
77 views

Dimerization of aniline to biphenyl

I've been looking for ways to synthesize biphenyl - $\ce{(C6H5)2}$. The Ullmann coupling is inaccessible, as bromobenzene is inaccessible in my country due to the manufacture of PCP. I had the idea to ...
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Stability of compound formed after attack of HCN (or any other nucleophile)on electron deficient center of carbonyl group

Will Benzaldehyde cyanonhidrin 1)be less stable than Benzaldehyde? 2)be less stable than cyanonhidrin formed due to an aliphatic aldehyde and HCN? 3)does aromaticty actually decrease stability of ...
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Why doesn't picolinamide undergo Hofmann rearrangement to form 2-aminopyridine? [duplicate]

I can not find a source that would explicitly state picolinamide undergoes Hofmann rearrangement to form 2-aminopyridine. Does this reaction occur, and if not, why?
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Comparing acidity between 4-hydroxybenzaldehyde and 2-hydroxybenzaldehyde

https://hmdb.ca/metabolites/HMDB0011718 https://hmdb.ca/metabolites/HMDB0034170 The above two links provide the pKa values for the 4-hydroxybenzaldehyde (pKa = 7.32) and 2-hydroxybenzaldehyde (pKa = 8....
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67 views

What are the resulting conjugate acid and base of phenol and 4-nitrophenol

I have to complete the equation 4-nitrophenol + phenol ---> and then label the acid, the base, the conjugate acid and the conjugate base. I think the answer ...
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Why does the reaction of Brady's reagent and cyclohexanone not also form an enamine-type product?

In this reaction in a Khan academy video, cyclohexanone reacts with Brady's reagent to form hydrazone product. My question is why doea Brady's reagent + cyclohexanone not also form an enamine product ...
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Why does Phenylalanine to Tyrosine release H2O?

So I was reviewing Tyrosine and Phenylalanine metabolism (according to this video) and maybe I'm missing something but in the first step, 1: Oxygen atom reacts with Phenylalanine to make up Tyrosine, ...
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Justification for using valence bond theory and molecular orbital theory together?

Elementary gen chem books will make the careful distinction between the two theories and then proceed to claim that chemists can use both to complement each other to explain the behavior of certain ...
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Redox reaction of cycloheptatriene ligand

The reaction I really don't understand is the second one which produces the cycloheptatriene ring with a positive charge. The only thing I can think of is that the hydrogen is being ejected and ...
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Selective reduction of aromatic nitro group

In the following compound, is it possible to selectively reduce the aromatic nitro group to an amine, as shown in the reaction? I fear that the methods usually used to reduce aromatic nitro compounds,...
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Why do electron-withdrawing groups deshield outer ring protons?

I understand that ring protons experience deshielding because the induced magnetic field (outside the ring) has the same direction as the external applied field, but shouldn't electron withdrawing ...
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Substitution in aryl halides

I need to propose a route for the synthesis of 2-(bromomethyl)benzonitrile from 1-bromo-2-(bromomethyl)benzene. In the attached figure, the structure of the starting compound and the species to be ...
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Nitro as a leaving group in an aromatic ring

I came across a chemistry problem posted on Discord. The objective is to propose a reagent that will enable the following reaction to occur: One proposed answer for the mysterious Reagent D is sodium ...
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58 views

How can Phthalocyanine be aromatic when it is not planar? [closed]

Even as Hückel's rule is not applicable in every scenario, especially in metallic clusters, it seems that organic structure need to be planar to show aromaticity. That being the case, Pubchem's ...
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106 views

Which of these protons are equivalent? Which NMR signals correspond to which protons?

Here are is the NMR spectrum and the compound (both images are the same spectrum, just close up). I know the deshielded signals are the aromatic protons and the ones ~6ppm are the alkene protons but ...
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48 views

Effect of substituents on aromatic character

Does the presence of substituents (electron withdrawing or electron donating) on an aromatic system have any effect on the aromatic character? In other words, would it be correct to say that benzene ...
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Should we consider reactant as the product of a no reaction?

If a reaction doesn't take place, should we call the reactant as the product? What is the convention? Let me illustrate the question with an example from JEE Advanced 2021, paper 1: The reaction of Q ...
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Why is the synthesis of graphene through alkyne trimerization not viable?

I have been looking for a rationale on this as massive polycyclic aromatic hydrocarbons have been synthesized this way, and with Graphene just being an indefinite expansion of aromatic rings, this has ...
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63 views

Name of a beehive like organic structure, is it aromatic? [duplicate]

I was just studying organic chemistry and came across a weird, yet beautiful, structure, don't know its name but its structure is given below:                                                 I wanted ...
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163 views

What are the major products when naphthalene reacts with ethyl chloride in the presence of AlCl₃?

From Arihant Test Drive, JEE Advanced 2020; Ramchaya builiding, Daryanganj, New Delhi, India; January 2019, p. 342: Napthalene gives 1-ethylnapthalene on reaction with ethyl choride in the presence ...
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For benzene, why are the first three pi molecular orbitals considered bonding, and the higher three antibonding?

Is it because all the molecular orbitals that are naturally occupied are all considered to be bonding orbitals? So for benzene, since the lowest three orbitals are all occupied (due to benzene having ...
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Partial rate factors in EAS

In the electrophilic aromatic substitution of benzene, at the para position in toluene, why do the partial rate factors follow the order $Br^+>Cl^+>NO_2^{+}$? I understand that if the ...
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SN1 mechanism on 3,5-dimethylbenzyl bromide [closed]

I wanted to see how to make the product on the right so my thought was to have an SN1 reaction to remove water and have the bromine ion attack making the product on the right hand side. Is this ...
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129 views

What is the mechanism of paracetamol synthesis from N‐acetylsulfanilic acid? [closed]

C can be converted to D with NaOH and heating at 300 °C. What is the mechanism of the reaction?
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Is it correct to say that benzene is more stable than cylcohexatriene due to delocalization?

I'm virtually all chemistry books I own say that benzene is more stable than the theoretical cyclohexatriene, by 150 kJ to be specific, due to the delocalization of pi electron density around the ring....
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Synthesis of allylic ether, starting with phenalene

I stumbled across a retro-synthesis question, for which I don't know the exact answer; I prepared two synthesis ways, but I don't know if they could be realized in a lab. The question is the following:...
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Action of EtONa/EtOH on compound containing -CN group

In the above question, I know compound A will be prepared by just replacing -Cl with -CN group in the starting compound. I wanted to know what work would be C$_2$H$_5$ONa/EtOH doing in order to make ...
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Branching Cyclic Hydrocarbons and Comparing Boiling Point

I am currently in organic chemistry and working on comparing the boiling and melting points of hydrocarbons. The question, in particular, is drawing a comparison between benzene and toluene's relative ...
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Aromaticity in cyclic ketones

I have read that, cycloprop-2-ene-1-one is aromatic and cyclopent-2,4-dien-1-one is antiaromatic. Basically this is visualized by visualizing the resonance structures of this. Similarly if I apply ...
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Does benzene sulphonic acids show steric inhibition of resonance / ortho effect?

I have read about ortho effects in aniline (steric inhibition of protonation) and benzoic acids but have not seen anything about Sulphonic Acids ($\ce{-SO3H}$) do they also show considerable ortho ...
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Side-chain Oxidation vs Oxidative Cleavage

When the above compound is subjected to acidified $\ce{KMnO4}$, can both side chain oxidation and oxidative cleavage of $\ce{C=C}$ bond occur? Or will one have priority over the other?
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What is the mechanism when 1-chloro-4-nitrobenzene reacts with NaOH?

The reaction mechanism in my textbook when 1-chloro-4-nitrobenzene reacts with NaOH is given as follows, When chlorobenzene reacts with NaOH the product formed is phenol with benzyne as the reaction ...
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How to convert benzyl alcohol to 2-phenylethanoic acid?

How can we convert benzyl alcohol to 2-phenylethanoic acid? This is what I have tried. Can someone tell me whether this is correct because I am not sure about the second reaction. In my textbook it ...
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What is the error in the number of aromatic isomers of C7H8O?

I am a student studying basic organic chemistry (isomerism) and was asked a question to find the number of aromatic isomers of $\ce{C7H8O}$.In fact this was a question in IITJEE exam. So I tried to ...
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Why does chlorine show a mesomeric effect in haloarenes and an inductive effect in haloalkanes?

Chlorine shows the +R effect in haloarenes and the -I effect in haloalkanes. Does chlorine do the same for all cyclic compounds or only for aromatic rings? Is this just another experimentally seen ...
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1answer
97 views

Electrophilic Substitution of Substituted Benzene

I know that phenol doesn't undergo the Friedel-Crafts Alkylation and Acylation reactions, because the reagent $\ce{AlCl3}$ forms a complex with phenol, as the oxygen atom donates it's lone pair to the ...
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Compare density of halogen substituted benzene rings

The correct decreasing order of densities of the following compounds is : (1) (D) > (C) > (B) > (A) (2) (C) > (D) > (A) > (B) (3) (C) > (B) > (A) > (D) (4) (A) > (B) >...
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Do contiguous monolayer aromatic structures retain the same magnetic susceptibility as the core constituents?

As the synthesis of Porphyrin monolayer strips is achievable, retaining the core aromaticity of the tetrapyrrole; does it still retain the same value of magnetic susceptibility of porphyrin? Does this ...
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606 views

Does Phenylacetylene undergo side chain oxidation with hot alkaline Potassium permanganate?

This question was asked in my book: To my knowledge, side chain oxidation with KMnO4 occurs only when a benzylic hydrogen is present. However this doesn't contain a benzylic hydrogen and hence ...
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1answer
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Friedel–Crafts acylation of substituted anisole

I am attempting to form a synthetic route to a tetrasubstituted benzene compound. In the scheme, there is a step that requires the formation of a carbon–carbon bond in the C-6 position of a methoxy ...
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429 views

Reaction of phenol with phosphorus tribromide

I know that aliphatic alcohols react with reagents like $\ce{PBr3},$ $\ce{PBr5},$ $\ce{SOCl2}$ etc. to give alkyl halides as a product. But what will happen if we put aromatic alcohols like phenols ...
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806 views

Reaction of naphthalene with sodium dichromate/sulfuric acid

I recently came across a question where naphthalene undergoes oxidation with sodium dichromate in presence of sulfuric acid. The given options were benzoic acid, phthalic acid, decalin, and tetralin. ...
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Ortho effect and the relative acidity in aromatic acids [duplicate]

What is the order of the acidity of 2-methyl benzoic acid and 2-isopropyl benzoic acid? I know about ortho effect which states that the acidity of ortho- substituted aromatic carboxylic acids is ...
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1answer
93 views

Can dimethyl sulphide be used for ozonolysis of benzene?

There is literature that suggests that ozonolysis of benzene occurs with ozone and $\ce{Zn/H2O}$. Can it take place with ozone and dimethyl sulphide?
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Nitration of haloarene

Question: Convert benzene to 4-bromonitrobenzene. My attempt: Answer given: Is my solution correct? Can aryl halodes react directly with $\ce{AgNO2}$ to form aryl nitrate?

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