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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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Why don't zwitter ions show ortho effect?

I recently came across a statement which said that zwitter ions are an exception to the ortho effect. Is it because the ions attract each other and the -COOH group is brought back into the plane ...
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4 views

Epoxy Resin Systems [closed]

How to formulate an epoxy resin system that only activates by specific temperature? How can I alter the activation temperature?
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15 views

Effect of H-bonding on o-nitrobenzoic acid

My argument here is regarding the acidity of o-nitrobenzoic acid being greater than p,m-nitrobenzoic acid. In o-nitrobenzoic acid, there is an intramolecular hydrogen bond which makes the bond ...
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35 views

Why Isn't Huckles rule applicable to more than 3 fused rings [duplicate]

In the following compound (Pyrene) why isn't Huckle's (4n+2) rule applicable? I do know it is applicable to only mono-cyclic ring systems but what changes when there are more than 3 fused rings? ...
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Electronic effects of substituents in the benzyne mechanism

On the topic of nucleophilic aromatic substitution (S$_N$Ar) reactions, the benzyne mechanism is discussed. When considering the position of substitution, electronic and steric factors are mentioned. ...
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2answers
72 views

Synthesize the trisubstituted benzene

I am trying to synthesize 1-(2-amino-4-chlorophenyl)ethan-1-one from benzene. The answer I came up with is that the benzene must undergo nitration first, then halogenation, then hydration for $\ce{NO2}...
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45 views

Arranging these aromatic amines according to their basic character

The problem asks to arrange theses amines in an increasing order of their basic character. Clearly 2 is less basic than 1, because $NO_2$ is a strong $e^-$ withdrawing group and it is going to show ...
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88 views

pi molecular orbitals of benzene

I found the following picture of the $\pi$ molecular orbitals of benzene. Now, I am having problem on understanding $\pi_3$ and $\pi_5 ^*$ In both of these, we can see that, on right and left, bond ...
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52 views

Why do the 2 carbon atoms does not participate in 2 molecular orbitals of benzene?

I have seen the below given molecular orbital diagram of benzene, I did not understand why does the 2 carbon atoms in $\pi_3$ orbital and $\pi_5$ orbital does not participate in overlapping.
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43 views

How do I obtain Chrysoidine from Benzene?

So, basically I can convert Benzene to Phenol using Dow's synthesis process and then use $\ce{NH3}$, $\ce{ZnCl2}$, $\ce{HNO2}$, $\ce{NaNO2}$ under 0-5 °C controlled temperature and convert the ...
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1answer
45 views

Substituent effects on acidity

It is said that 4-methylbenzoic acid will be a weaker acid than benzoic acid. 4-nitrobenzoic acid will be a stronger acid than benzoic acid. I don't understand why the methyl group on 4-...
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1answer
30 views

Pigmentation of aromates [closed]

So, they try to color naftalene, nitrobenzeen and benzene. Only one of them colors. They can say with certainty that this is nitrobenzeen. Right/wrong and why? Sorry if my English isn't that great, ...
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112 views

Are the following structures aromatic?

I have not seen this type of question anywhere so I do not know the answer. This is just a problem that has been roaming around in my head that I may have seen somewhere. My approach - Since ...
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1answer
34 views

Mechanism for formation of Quinol from a Phenolic Ether

What's the mechanism for formation of Quinol from the given phenolic substrate? The reaction seems to be an acid catalysed hydrolysis, but I'm not able to reach the final product. I guess the first ...
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Napthalene - Friedel Crafts Alkylation and Acylation [duplicate]

Where does Friedel Crafts Alkylation and Acylation occur in Napthalene? Are the reactions kinetic-thermodynamic controlled? Here's something I came across - While alkylation occurs at alpha ...
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1answer
152 views

Are there any reducing agents for reduction of nitrobenzene to aniline other than Sn/HCl?

I was taught that Sn/HCl should be used for reduction of nitrobenzene to aniline. Can I ask if there are any alternative reducing agents (for example, LiAlH4?) to do the same task?
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1answer
178 views

Why Benzene is a good solvent even while it is not polar [closed]

Consider for a moment, ether, THF, benzene and hexane. Why is the solubility of many organics in these solvents in the following order THF > ether / benzene > hexane What makes benzene a good ...
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1answer
71 views

Detailed description of hydroxy(phenyl)methanesulfonic acid?

Hydroxy(phenyl)methanesulfonic acid, or benzaldehyde adduct is the product of reacting benzaldehyde with sodium metabisulfite ($\ce{NaS2O5}$) solution. It is obviously a well-known and often used ...
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1answer
76 views

When to include or exclude lone pair counting electrons according to Hückel's rules?

When counting the number of pi electrons, in furan only one lone pair was included, but the other one was not. In the cyclopentadienyl anion (2nd aromatic compound in the picture) the lone pair was ...
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2answers
100 views

What is the expected product in the reaction of hydrogen chloride with allylbenzene?

Shouldn't it be 4th option since since the carbon attached to the ring is secondary as well as resonance stabilized?
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1answer
63 views

What hinders SN2 more: geminal alkyl group or alkyl group on the aromatic ring?

Which among these two (1-chloro-1-phenyl-ethane and 2-(chloromethyl)-1,3-dimethylbenzene) is more reactive towards SN2? I strongly believe that it should be Y because of lesser hindrance on ...
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36 views

Explain basic nature of aniline relative to ammonia in solvent phase

It's quite common to explain the fact that aniline is less basic than ammonia using resonance. But, I read in a book[1] that solvation effects are also the reason. The explanation is given in terms of ...
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Is steric inhibition of resonance, or of protonation, dominant in 0-substituted anilines?

There's a question about inhibition of resonance: Is steric inhibition of resonance or steric inhibition of protonation dominant in o-toluidine? If you look at Martin's answer he says that CH3 is ...
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3answers
467 views

Why do electron donating groups decrease the acidity of aromatic carboxylic acids?

If we look at the resonance structures of benzoate anion, we would see that some amount of positive charge is present on the ring and this charge can get delocalised on the ring, like this: Now, if ...
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161 views

Is ortho-nitro benzoic acid more acidic than formic acid?

We know that the Electron Donating effect of the benzene ring in benzoic acid makes it less acidic than formic acid! And we also now that whenever an ortho substituent is present in benzoic acid ...
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1answer
35 views

Is delocalisation of non-bonding electrons into the benzene ring possible in case of conjugate base of benzoic acid? [duplicate]

If we take a look at conjugate base of benzoic acid it is as given below: Now my question is: Is delocalisation of non bonding electrons(in the carboxylate part) into the benzene ring possible? ...
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2answers
119 views

Claisen rearrangement in substituted ring

This is an example of Claisen rearrangement, property of allyl vinyl/phenyl ethers. I believe that the allylic migration should take place to the position ortho to both $\ce{-CH3}$ and $-\ce{OR}$ ...
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1answer
65 views

Cyclisation reaction through hydrazine

The following reaction confuses me - I don't understand how and why it happened (couldn't figure out the mechanism): I thought this is some Wolff Kishner sort of reduction, but the reagents don't ...
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2answers
1k views

Why does chlorination of toluene stop at two chlorine atoms?

My instructor mentioned a reaction for preparation of benzaldehyde by chlorination of toluene in presence of sunlight to form benzal dichloride, which on hydrolysis gives benzaldehyde. However, I'm ...
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2answers
123 views

Phenol and Deuterated Sulphuric Acid

What happens when phenol reacts with $\ce{D2SO4}$ in presence of $\ce{D2O}$? How many hydrogens in total are replaced by deuterium? Is the hydrogen of the hydroxyl group and three hydrogens ortho ...
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1answer
149 views

Is the electrophile in sulfonation of benzene SO3 or SO3H+?

What's the electrophile in sulfonation of benzene? Is it $\ce{SO3}$ or $\ce{SO3H+}$? According to what my professor taught me, both $\ce{SO3}$ and $\ce{SO3H+}$ may be the electrophile involved - and ...
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2answers
260 views

Action of hot alkaline KMnO4 on tert butyl benzene

Side chain oxidation of aryl alkanes takes place if there is at least one alpha hydrogen present by all accounts I presumed that there would be no reaction. However the answer given was trimethyl ...
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1answer
72 views

Electrophilic aromatic substitution of napthalene

It is known that the $\alpha$-position (or 1-position) for napthalene is the preferable position for substitution to occur at. However, I am getting two different explanations as to why this is the ...
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1answer
118 views

Does rearrangement occur in Friedel Crafts alkylation or not?

In the reaction of alkylation of aromatic systems with the help of Friedel Crafts alkylation - the reagent used is alkyl halide in presence of appropriate Lewis acid. When is rearrangement observed? ...
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1answer
365 views

Reactivity comparison of phenol and toluene towards electrophilic substitution

Which aromatic compound is more reactive towards electrophilic substitution? benzene chlorobenzene phenol toluene Correct answer: phenol But, according to me, the answer should ...
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1answer
77 views

Why is bromobenzene more stable than benzene?

Benzene is 45 kJ/mol more energetic than bromobenzene. I understand that due to resonance in bromine to benzene in bromobenzene increase the stability but such an enormous amount of energy can't only ...
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1answer
151 views

Does a benzene ring continue to oscillate at absolute zero? [duplicate]

The carbon bonds in a benzene molecule oscillate between single and double bonds. As they do so, the distances between the carbon atoms changes (as the attached animated GIF illustrates). At absolute ...
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1answer
66 views

Naming a hexasubstituted benzene ring

In naming the attached compound, is there a reason it is termed: 3,5-dibromo-1-chloro-4-ethyl-2,6- dimethylbenzene as opposed to: 1,3-dibromo-5-chloro-2-ethyl-4,6-dimethyl benzene? Shouldn'...
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1answer
40 views

Help on alternative terpene names and naming schemes

I am a software developer and currently parsing data involving terpene profiles of plant samples. The data in question uses different ways of naming the same terpenes in-between samples and since this ...
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1answer
100 views

Find product of the oxidation of 2-methylnaphthalene with chromium trioxide

This is a question from an organic chemistry book. I did not understand the solution given in that book. Here's the solution given in that book, I know that CrO3 oxidizes methyl group of toluene, but ...
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1answer
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What is an aromatic alcohol?

The following question was given in NCERT Exemplar Problems (Class XII): According to Wikipedia: In organic chemistry, the aromatic alcohols or aryl-alcohols are a class of chemical compounds ...
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Trisubstitution on phenol [duplicate]

Why does tri substitution occur on phenol when bromine water(bromine in any polar solvent) is added to it? Shouldn't the bromine deactivate the benzene ring hence preventing further substitution?
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1answer
497 views

Are ortho, meta and para used in IUPAC nomenclature?

I was presented with the following question in an online test: To avoid any confusion, here are the arranged options: A. 2-Chlorotoluene B. 1-Chloro-2-methylbenzene C. B and D D. O-...
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1answer
74 views

How can we say whether or not an organic compound is soluble? [closed]

In the exam recently conducted by my school, they asked whether 2-hydroxyacetophenone is water soluble or not. I thought that since there is intramolecular H-bonding in this compund, it won't be ...
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1answer
71 views

Monobromination of napthalene derivative

How does this reaction take place? Why does the bromine attach to that one particular location? I do know that since is $\ce{FeBr3}$ is present only 1 $\ce{Br}$ will attach non-substituted areas of ...
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2answers
161 views

What determines the geometry of Nitrogen to be planar or trigonal pyramidal?

In the following molecule (1-(4-fluorophenyl)-4-[[1-(2-methoxyethyl)tetrazol-5-yl]-phenyl-methyl]-piperazine) I have seen its 3D structure using Jmol, and I see that both nitrogens on the middle ring ...
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1answer
85 views

What is the product of the reaction of diol with tosyl chloride followed by lithium aluminum hydride?

This question is about the structure of products X and Y. According to me, the answer should be only A (as OTs will substitute on benzylic carbon). But in the answer key, they have given B and D. ...
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1answer
107 views

Why is 5,6-dimethylidenecyclohexa-1,3-diene non-aromatic?

The compound 5,6-dimethylidenecyclohexa-1,3-diene is supposedly non-aromatic: But I have no idea why this is so. The compound is probably planar. All the atoms on the ring are $\ce{sp^2}$ hybridized. ...
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Do we need to acylate aniline before nitration to get mono-nitro products?

In general, aniline rings are very activated and lead to poly-X products (like 1,3,5-tribromoaniline). So, does aniline undergo polynitration as well? Do I need to acylate aniline to get a mono-ortho ...
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1answer
70 views

A strange case of aromaticity [duplicate]

The compound in question is given below This is one of several compounds that was listed in a JEE Advanced 2017 question about aromaticity. From the solutions it seems this compound is aromatic. ...