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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55 views

How to neutralize the stink of decomposed fish?

Recently I discovered for myself an interesting way to easily produce home made plant fertilizer that is quite effective. It's fish emulsion - 1 part fish wastes(skin/bowels) to 2 parts water placed ...
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Is 1,2-diphenylbenzene aromatic? [duplicate]

Ignore misleading duplicate tag Below is a picture of a compound with $3$ benzene rings, where no two of them are in the same plane. An interactive model of the compound can be found here Is this ...
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1answer
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Electrophilic substitution on Borazole

As Borazole ($\ce{B3N3H6}$) is aromatic, it shows electrophilic aromatic substitution. Now, my question is when borazole undergoes electrophilic aromatic substitution reaction, on which atom does the ...
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1answer
78 views

Comparison of carbocation stability in bicyclo compounds

Question Which is the most stable carbocation ? Answer My attempt I answered as 1 as the first one had +M of -O- and hyperconjugation effect as the positive charge is at para position. Why is the ...
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2answers
226 views

Formation of toluene from (cyclobutane-1,2,3-triyl)trimethanol using conc. sulphuric acid

In my book this reaction is given without any mechanism: I thought that simple dehydration reaction is going to take place with rearrangement of the carbocation but I have no idea as to how toluene ...
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Can the inner amine groups of Bacteriopheophorbide A become positively charged in aqueous solutions without the use of very strong acids?

In an attempt to calculate the pKa of the carboxylic acid group of Bacteriopheophorbide A (BPheo, Pubchem), I generated the structure in MarvinSketch (ChemAxon product) and I came across an ...
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57 views

Clar's rule of polycyclic aromatic hydrocarbons

Clar's rule states that the Kekulé resonance structure with the largest number of disjoint aromatic π-sextets, i.e., benzene-like moieties, is the most important for characterization of properties of ...
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2answers
172 views

Mechansim of reaction between 1‐bromo‐2‐fluorobenzene and furan in the presence of Li/Hg

Problem From FITJEE AITS test series: What is the mechanism of the following reaction? Solution My approach It looks like Birch reduction with $\ce{Li}$ converting to $\ce{Li+}.$ But I can't make ...
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4answers
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Most favorable position of attack of an electrophile on 4-trifluoromethyl-1,2-diphenylbenzene

Problem This problem is from a FIITJEE AITS paper Which position is most favorable for the attack of an electrophile? Answer My attempt The more favorable position for attack should be the on the ...
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2answers
313 views

Solubility of ortho- and para-nitrophenol in benzene

Which one between o-nitrophenol and p-nitrophenol is more soluble in benzene? And what is the reason? If the solvent had been polar, hydrogen bonding would have provided a lot of explanation, but what ...
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357 views

Is benzocyclobutadiene aromatic or anti-aromatic?

My teacher told that benzocyclobutadiene is both aromatic and anti-aromatic. I do not understand why. Can anyone explain?
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In which nucleophilic aromatic substitution rate is faster m-fluoronitrobenzene or p-fluoronitrobenzene? [closed]

In which nucleophilic aromatic substitution rate is faster: m-fluoronitrobenzene or p-fluoronitrobenzene?
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Relative reactivity of alkyl and aryl halides in nucleophilic-substitution reactions

In case of alkyl halides, the order for relative rates of reactions is $\ce{RI > RBr > RCl}$. The reason is clear that $\ce{I-}$ is a better lg because of negative charge stabilisation and also $...
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Steric Effects in Friedel-Crafts Reactions

I recently came across a Friedel-Crafts reaction happening between benzoyl chloride and mesitylene with $\ce{AlCl3}$ as a catalyst. Apparently this reaction doesn't occur due to steric effects even ...
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1answer
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Why do alkylarenes react with alkaline KMnO4, but not benzene? [closed]

Benzene($\ce{C6H6}$) does not react with alkaline $\ce{KMnO4}$, however alkylarenes react when there are benzylic hydrogens. What could be the reason for this? Thanks in advance
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Reaction of cinnamic acid with Br2/Na2CO3

The first reaction produces benzaldehyde, and the next one (perkin's condensation)produces Cinnamic acid.(X) Now the treatment of X with $\ce{Br2/Na2CO3}$ is whats troubling me. $\ce{Na2CO3}$ being a ...
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1answer
78 views

Would any alkene possibly aromatize with proper conditions?

I was reading about 2 specific reactions: polymerisation of alkene and aromatization of alkane (of a sufficient size). I thought why can't, having a condition that favored both these reactions be ...
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1answer
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Phenoquinone vs benzoquinone [closed]

Are phenoquinone and benzoquinone the same thing? When I searched for the colour of benzoquinone I found that it's yellow. But when I searched oxidation of phenol in air. It states that it turns pink/...
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1answer
117 views

Which is the major product of bromination of 3-(dimethylamino)benzamide, ortho or para?

I know that A will most probably not happen because of high steric hindrance. However between B and C, will B become the major product? Because $\ce{-N(CH3)2}$ is less bulky compared to $\ce{C=O-NH2}$,...
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2answers
68 views

When we cannot use Friedel-Crafts acylation to insert alkyl group?

Questions: Show a probable synthethic pathway to obtain the first molecule, I. Will the same strategy be used to insert the alkyl group for J. Explain. My answers (please tell me if there is any ...
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What the product of this reaction?

The reaction is as follows, with (i) being my answer, and (ii) being the correct answer in the book. My question is why is the product (ii) formed here and elimination not favoured here? I think that ...
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1answer
38 views

Benzene - MO states [closed]

When constructing the different combined molecular orbital combinations (from the original 6pi orbitals) we normally say that p orbitals "combine" to produce the different molecular orbitals ...
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191 views

Ortho-para directing and meta directing groups: Activating or deactivating the aromatic ring?

Determine the reactivity of the above compounds (activating or deactivating; ortho-para or meta directing). Explain your answers. You may use resonance structures in your explanation. Which molecule ...
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1answer
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Mechanism for simultaneous reduction of nitro group (into aniline) and aromatic substitution (into benzonitrile) by Ethyl cyanoacetate?

I stumbled upon this paper when I'm trying to look at established protocol to synthesize one of the compounds (compound IIk) mentioned in the paper. Studies on Aromatic Nitro Compounds. V. A Simple ...
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Why does 1,4-diiodobenzene have a non-zero dipole moment?

From this answer, I came to know that 1,4-diiodobenzene has a dipole moment of $0.19~\rm D$ in benzene at $20\ ^\circ\rm C$. On the basis of symmetry, I'd expect the bond moments due to the difference ...
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1answer
92 views

Why does FeCl3 react with carboxylic acid, but not with sulphonic acid in this question?

I was solving a question where I was asked to identify the reagents given in the question which could react with a compound provided. The first compound was methanoic acid. One of the reagents given ...
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2answers
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Does Cl- Have more -I effect or +M effect ( Resonance effect)?

In this question my answer was (A) because i though $\ce{NH2}$ group would give more electrons than $\ce{Cl-}$ . But the correct answer is (D) and my teacher's reason is that chlorine has more ...
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Why isn't formation of benzyne a 1-step process?

According to "Organic Chemistry as a secondary language", during elimination-addition, formation of benzyne involves 2 steps (as shown in the bottom photo). I wonder during 2nd step, it is ...
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111 views

Dipole Moment of p-dibromobenzene

What is the dipole moment of p-dibromobenzene? I know that p-dichlorobenzene has zero dipole moment, but my teacher said that this is not the case for bromine. I am still confused and feel its dipole ...
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2answers
348 views

Alkylation of benzene

I was solving a question where I had to determine a way to convert benzene into n-propyl benzene. I figured out a way by first performing Friedel-Craft acylation with propanoyl chloride and then ...
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1answer
45 views

Is is possible to add NO2X, AlX3 to achieve nitration of benzene?

According to Organic Chemistry as Secondary Language (2nd semester), for nitration of benzene, the general way is to add $\ce{HNO3}$ and $\ce{H2SO4}$ and it said to make $\ce{NO2+}$. $\ce{(AlBr3 + ...
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why the terminal Br/Cl is an electrophile in AlBr5/AlCl5 complex? [closed]

In halogenation of benzene, e.g. bromination, $\ce{AlBr3}$ and $\ce{Br2}$ is added in order to make $\ce{Br+}$ by forming delivery agent $\ce{AlBr5}$ (step 2 of picture). Why is the terminal (...
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Predict the products of the following reactions with Mechanism [closed]

1 My Attempt : The correct answer is C. I tried rearranging similar to claisen rearrangement but I have no clue how to go forward. I know that option A is wrong and that the product is pretty easily ...
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2answers
134 views

Why is biphenyl not planar? [closed]

I've seen in a lot of books that biphenyl is not planar. I don't know why that is because both the carbon are $\mathrm{sp^2}$ hybridized so it should be planar. Can someone explain it to me?
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Friedel-Crafts's alkylation of Toluene [duplicate]

In the Friedel-Craft's alkylation of Toluene with $\ce{CH3Cl}$ in the presence of $\ce{AlCl3}$, the major product was meta - substituted. My teacher gave it to me as an exception. Is there any ...
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1answer
58 views

The increasing order of reactivity of substituted benz0yl chlorides towards nucleophilic substitution

Arrange the following compounds in the order of their increasing reactivity towards nucleophilic substitution: The answer to this question is $[3<2<1<4]$. We have to compare the positive ...
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1answer
95 views

How do I prepare the following compound from diphenylmethane? [closed]

I am having trouble with the preparation of this product from diphenylmethane as a starting material. One of my thoughts was to attach the butene into the structure, but I don't see how it is viable. ...
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1answer
206 views

Preparation of p-chlorobenzoic acid from p-chloronitrobenzene

I was reading my book where I spotted the preparation of p-chlorobenzoic acid from p-chloronitrobenzene. The preparation method there was given as such: $\ce{Sn/HCl}$ $\ce{NaNO2 + HCl}$ ($\pu{0-5 ^\...
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2answers
908 views

Benzene to phenol in a single step

My teacher told me we can convert benzene to phenol within a single step using $\ce{V2O5}$/ $\ce{O2}$ at 300 ⁰C (not 500 ⁰C). Later I searched for that reaction but I couldn't find it in all over ...
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1answer
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What happens to the NMR of an alcohol when D2O is added?

What difference you expect in the 1H NMR spectrum of phenol in $\ce{CDCl3}$ after a drop of $\ce{D2O}$ is added to the test tube? 1) Since the $\ce{-OH}$ of the phenol is quite acidic, it undergoes ...
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1answer
209 views

How to convert benzene to N,N-dimethylbenzamide?

This is my solution to convert benzene to N,N-dimethylbenzamide. If you think is the right way, even just saying the equations are correct would help me! Thanks in advance.
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What explains the stability of aromatic compounds? [duplicate]

We are taught in High school that aromatic compounds are highly stable. Why is that true? Also, Why are Antiaromatic compounds highly unstable? Aromatic compounds have 4n+2 (n is a whole number) ...
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1answer
52 views

Treating styrene in the atmosphere

I was actually inspired to ask this question in certain circumstances. In the outskirts of my city, there happened to be a styrene gas leak early morning today which killed thirteen and hospitalized ...
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1answer
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Safe coating to make a 3D printed respirator mask airtight [closed]

What is a good example of something safe that could be applied as a coating layer to the walls of a 3D printed respirator mask to make them truly airtight (seal pores and fissures) while (ideally) ...
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0answers
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Seeing a case where both + and - mesomeric effect is shown

I came up with that -N=O group shows both +M and -M and I understand that. In my textbook it was written that " -N=O group attached to benzene shows both + m and -m depending on the nature of other ...
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2answers
69 views

Which resonance structure would be favorably contributed to the actual structure?

Total number of pairs of resonating structure in which second is more favorable than first: I know (d) and (e) have second structure more stable. (f) has both same. According me to, (a) and (c) ...
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1answer
50 views

Para effects on substituents in aromatic compounds

I wanted to know how to compare the following compounds on basis of acidic strength. I have to find the acidic strength of following compounds with $\mathrm{X}=\ce{CH3, \ OCH3,}$ and $\ce{NO2}$. For ...
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31 views

Resonance energy in benzene

Quoting from my textbook: Although stabilized by resonance compared with other carbocations, its resonance energy is much less than that of the starting benzene ring. Here is more context : Isn'...
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0answers
33 views

nucleophilic aromatic substitution reaction [closed]

I am in a project in organic synthesis writing about nucleophilic aromatic substitustion reactions. I cant´t figure out why the nucleophile (benzylmethylamine) attacks the chloro-binded carbon when ...
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1answer
102 views

Reaction of benzene diazonium salts with different compounds

1. $ \ce{ArN2+Cl-}$ gives addition product with $\alpha,\beta$ unsaturated acids, with decarboxylation being integral part of reaction. For example, $$\ce{ArN2+Cl- + Ph-CH=CH-COOH -> Ph-CH=CH-Ar +...

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