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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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Aromatic NMR in benzyl alcohol [on hold]

Do you know the multiplicity of aromatic hydrogens in benzyl alcohol? In many files on internet I see "5H multiplet" but I want more precision please.
2
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1answer
41 views

Friedel-Craft reaction with amide substituent

In this question, I know that aniline will not undergo FC reaction as it forms a complex with $\ce {AlCl3}$ and precipitates out. The answer given is (c) and I agree with it. However, the benzene ring ...
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0answers
20 views

Order of dipole moment [closed]

Arrange o-chlorotoluene, m-chlorotoluene, p-chlorotoluene in increasing order of dipole moments. The answer is the same order as given but I don't get why.
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0answers
28 views

Pyrimidine chemistry

Why C4 position in pyrimidine ring is more reactive then C2 position in nucleophilic aromatic substitution and Pd chemistry? Should not be the C2 position the most reactive because of the effect of ...
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0answers
10 views

To Check the basicity difference [closed]

$$$$$$$$Give the correct order basicity of following compounds....,I have tried my best to solve this question but cannot solve it! can you solve it???$$$$$$$">
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1answer
20 views

Which of the following compounds will form significant amounts of meta product during mono-nitration reaction? [closed]

Hi, I tried to answer this question based wholly on the concepts of inductive effects. But haven't gotten anywhere with it. I would appreciate any help regarding these questions: What condition ...
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0answers
29 views

What is the product when 1,4,6-trifluoroazulene is treated with sodium methoxide?

My logic During substitution via Path 1 and Path 2 aromatic intermediates are formed. Via path 3 anti aromatic intermediate is formed. Therefore reaction takes place via path 1 and path 2 only. ...
12
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2answers
390 views

Does aniline react with diazonium ions at C or N?

In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major ...
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34 views

Synthetic route for conversion of benzene to 1,4-di(hydroxymethyl)benzene

I tried something like: and I am not sure about it
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0answers
57 views

Benzene diazonium chloride and ethanol

Benzene diazonium chloride is reduced to benzene by ethanol which itself gets oxidised to ethanal. Most reactions of diazonium salts are due to nucleophilic substitution on the carbon attached to ...
9
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1answer
71 views

Are nucleophilic aromatic substitutions stepwise or concerted?

Recently, there has been a lot of discussion about nucleophilic aromatic substitution (SNAr) reactions apparently being concerted instead of stepwise (e.g. Krämer, K. Textbook aromatic substitution ...
2
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0answers
30 views

What is the peak at 3200 cm⁻¹ in the IR spectrum of Benzocaine?

Benzocaine has the following IR spectrum: and here is it's structure: From what I understand: The two leftmost peaks are the antisymmetrical and symmetrical stretchs of the amine group. Just before ...
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0answers
41 views

What is the major product of the nitration of N,N-dimethylaniline? [duplicate]

What is the major product when N,N-dimethylaniline, $\ce{C6H5N(CH3)2}$, reacts with concentrated nitric acid (conc. $\ce{HNO3}$) in presence of concentrated sulphuric acid (conc. $\ce{H2SO4}$)? Here, ...
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2answers
94 views

Effect of nitro group basicity order of o,m and p nitroanilines?

Would someone please help me with this? The order of basicity of o,m and p nitroanilines is m>o>p. My book states that ortho isomer has -I effect, -M effect as well as ortho effect, and meta isomer ...
11
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1answer
360 views

Is phosphorine (C₅H₅P) aromatic?

Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is ...
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0answers
36 views

Which is most stable resonance structure of 4-nitrophenoxide ion?

According to my coaching module the first structure is more stable. Why is this so? I feel both must be approximately equally stable since negative charge is on oxygen in both cases. Would someone ...
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0answers
35 views

Hydrogenation of acetophenone

How does acetophenone Ni/H2 at 25 °C give a pair of enantiomers (given as chapter practice question in a book)? I thought it should just give ethyl benzene.
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1answer
59 views

Can aromatic rings be cyanated using cyanide as a nucleophile? [closed]

For example, can I convert chlorobenzene into benzonitrile by using potassium cyanide as the reagent?
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0answers
31 views

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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0answers
45 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 ...
0
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0answers
36 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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0answers
38 views

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
77 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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0answers
65 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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0answers
235 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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1answer
54 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 ...
2
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1answer
54 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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1answer
135 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 ...
0
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1answer
48 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 ...
1
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0answers
32 views

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
259 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
387 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
76 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
121 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
133 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?
3
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1answer
70 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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0answers
39 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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0answers
71 views

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
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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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1answer
233 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
46 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? ...
5
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2answers
164 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 $-\ce{OR}$ ...
4
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1answer
83 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 ...
8
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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 ...
5
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2answers
167 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 ...
4
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1answer
265 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 ...
5
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2answers
620 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 ...
9
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1answer
96 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 ...
2
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1answer
160 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? ...