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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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Basic strength of the compound with an conjugate, and an aromatic amine

According to the source of the question answer is c>a>b but shouldn't the order be c>b>a as (a) is attached to a benzene ring and the lone pair will be delocalized?
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Reimer–Tiemann reaction of 2-naphthol [on hold]

What are products obtained when 2-naphthol or β-naphthol is subjected to Reimer–Tiemann reaction? I am confused whether formylation will take place at the 1st position or 3rd position with respect to ...
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22 views

Aromaticity when lone pair atoms present [duplicate]

I am having trouble identifying aromatic compounds when elements other than carbon, like oxygen, nitrogen are present. I know the (4n+2) Huckel rule of electrons required for aromatic/anti aromatic ...
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24 views

Butadiene for yoga mats [closed]

I am researching new ways to make a better yoga mat.Can Butadiene be used in production of Yoga mat? Can Butadiene be infused with essential oils? Thank you
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1answer
29 views

Highly conjugated compounds and the effects of substiuents

TLDR, what is the effect of electron donating and withdrawing groups on the UV-Vis absorption spectra of pi-conjugated system? For a conjugated system, my understanding is that as the extent of ...
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1answer
35 views

Reaction between phenylamine and halogens

I understand that phenylamine is considerably more reactive than benzene, meaning that it is able to react with bromine water to give 2,3,6-tribromophenylamine. But I was then wondering why I haven't ...
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Conversion of benzenediazonium chloride to benzene using lithium aluminium hydride

Why does benzenediazonium chloride get converted to benzene upon reacting with $\ce{H3PO2}$ and not $\ce{LiAlH4}$ ? Also, what is the reaction mechanism of the reaction with $\ce{H3PO2}$ ? This ...
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Nitration of m-bromochlorobenzene

1) What could be the most plausible explanation to the very low percentage of the nitro group attacking the site between bromine and chlorine? - is it solely because of steric hinderence - or is it ...
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Why benzene has more heat of hydrogenation than cyclohexene? [duplicate]

According to me, benzene is more stable than cyclohexene due to its aromatic nature. Therefore the heat of hydrogenation of cyclohexene should be more than benzene (because I read that heat of ...
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1answer
32 views

Degree of unsaturation of naphthalene

Double Bond Equivalent/Degree of Unsaturation 25. Degree of unsaturation in is (a) 6; (b) 7; (c) 8. There are two rings and six double bonds in structure so degree of unsaturation ...
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Confusion about orienting effects in o-chlorotoluene

I'm confused about where the next substituent in the electrophilic substitution of o-chlorotoluene will land. My question comes on the background of having 3 different sources of information that say ...
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Which group will show mesomeric effect?

If both $\ce{-CH2+}$ and $\ce{-NO2}$ groups are attached to benzene ring then which group would be more effective in showing $\ce{-M}$ effect?
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What are the pi-MOs in anisole like?

The $\pi$-orbitals of benzene are well known and given in any standard undergraduate textbook. When considering anisole, phenol, etc, a lone pair in a p orbital of the O can delocalise into the $\pi$-...
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Are pi electrons in 1,3 cyclobutadiene delocalised? [duplicate]

The original question in my test was whether all bonds in the aforementioned molecule are of same length. According to the solution booklet, it is not because pi electrons are not delocalised due to ...
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Heating Dry Benzenediazonium Chloride

If we heat BDC with water then phenol is formed. I was wondering what would happen if we heated dry benzenediazonium chloride. I know that on heating benzenediazonium fluoroborate we obtain ...
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Question about the cyclic hemiacetal form of compounds [closed]

Why is D not a valid answer for this question?
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Why might the yield of my synthesis of triphenylmethanol be so poor?

I performed the classic Grignard reagent formation leading into the preparation and purification of triphenylmethanol using phenylmagnesium bromide as my Grignard, and benzophenone as the reagent for ...
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1answer
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Why 1-ethenyl-3-ethyl-5-ethynylbenzene has that name?

I would priorized these funtional groups based on two options (following the ciclohexane rules): Molecular weight Representing each pi bond as a alkane branch. e.g. Ethenil as a isopropil backbone. ...
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Are the electrons delocalized around both rings in tryptophan or just the outermost ring?

I often see it drawn with the "circle" only in the outer ring, which leads to my confusion. Should the circle (or dotted lines) be drawn in both rings (delocalized over both)? One book says there are ...
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2answers
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What about the aromaticity of cyclopropenylidene?

Here's a compound which we have to tell whether it's aromatic or not. Drawing pi-orbital for the 3-membered ring, I think there are only 2 pi electrons delocalised all over the ring. The orbital ...
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29 views

Regarding Clemensen Reduction of the following compound [duplicate]

While I was doing problems on reduction of aldehydes and ketones, I encountered this particular question Here, I know that Clemensen reduction reduces the ketone group to $-CH_2-$ group. But, the ...
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1answer
59 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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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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1answer
71 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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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. ...
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2answers
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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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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 ...
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191 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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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
410 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 ...
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1answer
381 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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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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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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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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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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112 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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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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1answer
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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
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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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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
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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
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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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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
74 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
433 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
688 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
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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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232 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
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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?