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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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What test would give me a qualitative recognition of the presence of benzene in methylphenidate?

I need a couple of tests to recognize the presence of benzene in my compound (methyphenidate). I've looked into tests with bromide or Freidel-Crafts reactions but I'm not sure if both or neither would ...
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Conflict: Sandmeyer reaction and Gattermann reaction

So it is known that benzene diazonium chloride when reaction with cuprous(I) chloride would produce a chlorobenzene which is called Sandmeyer reaction. Now for the same salt, if we react it with ...
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what will be the major product on mononitration of para-isopropyltoluene? [closed]

para-isopropyltoluene means an isopropyl group attach to the para position with respect to the methyl group of toluene. mononitration means treating with concentrated HNO3 and concentrated H2SO4 to ...
7 votes
6 answers
3k views

How can I determine the size of tropolone molecule?

How can I determine the size of a tropolone molecule? It's a seven-membered aromatic ring with =O on the first carbon and -OH on the second carbon. Is there any software available?
13 votes
2 answers
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Does folic acid contain a benzyl or a phenyl group?

I'm studying for my MCAT currently and I stumbled upon this question. It gives the structure of a folic acid molecule and asks what functional groups can be found within the molecule. I understand ...
8 votes
2 answers
861 views

Why does the Wurtz-Fittig reaction occur?

In the Wurtz-Fittig reaction, an aryl halide and an alkyl halide react with sodium in the presence of dry ether to give R-Ar as the major product. Why is the coupling of R and Ar favoured? In other ...
2 votes
0 answers
32 views

Nonplanar polarization in allenes and aromatic compounds

I recently came across this elaborate article on electrophilic aromatic subsitution. In the third chapter "General mechanistic considerations in electrophilic aromatic substitution" the ...
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0 answers
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Delocalisation of electrons: Benzenecarboxylic acids

Naturally, the benzene ring will have a degree of delocalisation in the ring due to the pi cloud. Similarly, the carboxylic acid group will also have a degree of delocalisation. Correct me if Im wrong,...
10 votes
2 answers
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Bromination of acetanilide

Why does acetanilide gives exclusively para isomer. I know that -I of nitrogen must decrease the yield of ortho product, but still it should be made in accountable amounts. Where am I going wrong. I ...
3 votes
1 answer
831 views

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 ...
2 votes
1 answer
104 views

Is the 4H-Pyran Cation aromatic?

I guess I'm just trying to understand what "cyclic resonance" really means, from all the examples I've come across its always a cyclic system where the pi-electrons go all around the ...
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Stability order of xylenes [duplicate]

M-xylene is the most thermodynamically stable amongst the three isomers due to hyperconjugation. Can we comment on the stability order of the other two forms as well? If yes, what would be the order ...
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1 answer
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Steric Inhibition of Resonance in ortho-substituted Benzoic Acids

It is given that due to Steric Inhibition of Resonance (SIR), the acidity of ortho-substituted benzoic acid increases with respect to benzoic acid. However, I'm unable to understand the reason behind ...
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1 answer
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Why is chlorine atom in chlorobenzene deactivating the benzene ring when it has M+ effect, which is stronger than I- in other cases?

McMurry says that halogens are deactivating the benzene aromatic ring, but in contrast, -OH group in phenol is (strongly) activating the ring. So I- in halogens is much stronger than I- in -OH group? ...
4 votes
1 answer
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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 ^\...
1 vote
2 answers
473 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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1 answer
2k views

Oxidizing toluene to phenol [closed]

Can toluene be oxidised with air to produce phenol? What catalysts are needed?
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2 answers
4k views

Directional nature of the acetamido group in electrophilic substitution reaction

Here, in $\ce{CH3CONH2 -}$ group, the nitrogen has a lone pair and can thus activate the benzene ring along with having an ortho-para directive effect in the following manner: However at the same ...
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35 views

Why nitration of aniline carried out after acetylation give ortho and para major products?

I was reading about the meta directing nature of anilinium cations and the answer mentioned that these reactions are usually carried out with 90-98% sulphuric acid. At these concentrations I would ...
6 votes
1 answer
9k views

How to explain (non-/anti-) aromaticity in fulvene with the help of resonance structures?

Can someone please explain why the resonance structures of fulvene 1 is non-aromatic and 2 is anti-aromatic? Why is fulvene non-aromatic, even though it has four $\pi$-electrons and no $\mathrm{sp^3}$...
5 votes
0 answers
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Mechanism of Cu Catalyzed reaction between Benzoic acid with DMF

I'm looking for the mechanism of this reaction that I have stumbled upon. It is believed to be a radical reaction and I can kinda see that but I'm not convinced that I can understand all of the steps, ...
4 votes
2 answers
578 views

I left scented candles in a polypropylene container. How do I remove the smell?

I left scented candles in a polypropylene container, for many weeks. How do I remove the smell? I've tried: Hand wash with Dish Soap (a few times) Hand wipe with Isopropyl Alcohol (a few times) ...
-3 votes
1 answer
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ease of dehydration [closed]

ease of dehydration for the following alcohols is? I understand the most easiest would be for III, but shouldn't it be easier for I than for II? because II forms an anti aromatic compound? But the ...
-2 votes
1 answer
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Why is o used for hydroxy groups in IUPAC naming instead of saying 2-hydroxy [closed]

For this question, i marked compound II correct as 2-methylbenzaldehyde and got the question correct, but for compound I, i marked it wrong and suggested the name to be 2-hydroxybenzaldehyde. I got ...
1 vote
1 answer
112 views

1-Bromo-4-tert-butylbenzene reaction with NaNH2 [closed]

I'm struggling to grasp how the reaction would turn out. Could you help? My idea was that the bromide atom will get replaced by the amino group of $\ce{NaNH2}$, but when I google, I read that $\ce{...
12 votes
1 answer
561 views

Color of methoxy substituted phenyl rings when heated in the presence of acid

Anyone who's familiar with organic synthesis will probably have came across the DMB and PMB protecting groups. When TLC-ing compounds containing these protecting groups using common stains like ...
-1 votes
2 answers
131 views

Which one has a greater dipole moment: benzamide or benzoic acid?

My guess is that, since the relative electronegativities are similar, therefore the difference would arise only due to magnitudes of difference in electronegativities. And hence the strength should be ...
1 vote
0 answers
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DIY method for regenerating activated carbon in air filters

I am interested in regenerating activated carbon used in general house-hold air filters. I am looking for a sufficiently efficient and easy method to do this in home setting. A little tinkering in a ...
5 votes
2 answers
278 views

Is there a symbol or representation for tolyl groups as there is for the phenyl group?

Is there a symbol or representation for tolyl groups as there is for the phenyl group? Phenyl group is often represented by "Ph" when for a matter of space you can not draw the entire ...
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1 answer
86 views

Why do halobenzenes not give Birch reduction?

I was studying Birch reduction and my book says halobenzene and phenol do not give Birch reduction. I want to know why these two type of compounds do not give Birch reduction. I also want to know if ...
14 votes
0 answers
444 views

What explains the color in clear sigma versus green pi complexes formed by methylbenzene?

Peter Sykes mentions in Guidebook to Mechanism in Organic Chemistry (6th ed.) on p.132 that there would significant differences in physical properties of the resultant mixture when we: React ...
1 vote
1 answer
121 views

How does the following cyclization reaction work?

The following is a reaction from a school provided lab manual. However, I am unable to find anything similar to the cyclization reaction taking place. All of the reactions I have found online make use ...
2 votes
1 answer
799 views

Identify structure of compounds from their reactions and molecular formula

Compound P ($\ce{C7H6O}$) on refluxing with aqueous ethanolic $\ce{KCN}$ solution for 1 hour, forms Q ($\ce{C14H12O2}$). Q on oxidation gives R ($\ce{C14H10O2}$). R on refluxing with aqueous $\ce{NaOH}...
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Is this fused ring molecule aromatic? [duplicate]

In my notes, I can see that it is listed as anti-aromatic because of the 16 electron ring current that would be formed on the periphery of the entire molecule were the right benzene ring drawn in the ...
0 votes
1 answer
43 views

Non-catalysed exhaust gas

I'm writing up an academic paper (medical) on in-car exhaust levels and their effect on health. So as to ensure detection of leak-points that are located further along than the catalytic converter, in ...
10 votes
1 answer
869 views

Aromaticity of fused rings

I understood how to find aromatic nature of single aromatic rings (like benzene) or that of combination of rings which are independently aromatic, such that the electrons of one ring do not enter into ...
2 votes
0 answers
131 views

Removing DCC and its by-product from Steglich Esterfication

In my small research, I want to synthesize 3 alkyl gallates (ethyl gallate, butyl gallate, and hexyl gallate), and here's my overall reaction using Steglich esterification): However, from reading ...
0 votes
1 answer
136 views

Is acetophenone a saturated compound?

In many of the sites in online, acetophenone is mentioned as an unsaturated compound because of the presence of C=C bond in the phenyl group. But, many of my teachers say that it is a saturated ...
6 votes
1 answer
635 views

How is 4H‐1,4‐oxazocine aromatic?

I’ve found 4H‐1,4‐oxazocine in my chemistry book and I’m perplex as it states as aromatic: I can count six electrons on p orbitals which could satisfy Hückel’s $n = 1,$ but the oxygen is sp3-...
8 votes
1 answer
4k views

Why is porphyrin aromatic?

I was asked which of the following were aromatic: My understanding of aromatic nature is, that the molecule must be cyclic, planar, every atom in the ring must be $sp^2$-hybridized and the molecule ...
1 vote
0 answers
70 views

Is 2,5-dimethylidenecyclopent-3-en-1-ide aromatic?

Ah yes, the age-old question. I understand from previous posts on this website that aromaticity can't be defined with using four rules. But I was curious about this particular anion: It certainly ...
0 votes
1 answer
133 views

Aromaticity of a fused ring compound

On a test, I marked this as aromatic, but the answer key says it's wrong. My thought process: It has 10pi electrons, so it follows Huckel's rule All carbons are sp2 hybridized It is cyclic Every atom ...
1 vote
1 answer
272 views

Can a carbocation ever be more stable than a neutral molecule?

The question is about finding the most stable molecule or species. Now my thought process was that cyclopropenylidene(1) was a carbene so would be unstable even though it is aromatic. Cyclopenta-1,3-...
5 votes
1 answer
190 views

How is nitrogen the most powerful electron donor in aromatic rings?

In Clayden, page 735, Aromatic Heterocycles 1:Reactions: The other simple five-membered heterocycles are furan, with an oxygen atom instead of nitrogen, and thiophene, with a sulfur atom. They also ...
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185 views

How phenyl shift is possible in Benzil-benzilic rearrangement?

We know $\ce{C-C}$ bond is much stronger than $\ce{C-OH}$ bond (because similar sized atoms have maximum overlap) as in case of phenyl-carbonyl carbon bond. Also due to resonance there is double bond ...
13 votes
2 answers
6k views

Why is benzoic acid a stronger acid than 3-aminobenzoic acid?

Why is benzoic acid a stronger acid than 3-aminobenzoic acid? Obviously at meta position, only negative inductive effect will operate. But, how does that make it a weaker acid than benzoic acid?
1 vote
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Why is the melting point of meta-diiodobenzene higher than that of ortho-diiodobenzene?

I'm currently trying to reason for as why the melting point of meta-diiodobenzene higher than that of ortho-diiodobenzene and I'm unsure of what to say. I understand the para isomer has the highest ...
5 votes
0 answers
130 views

Electrolytic reduction of nitrobenzene in differing media

In my lecture notes it is given that in a weakly acidic medium, nitrobenzene on electrolytic reduction gives aniline, which makes sense to me because there is ample H+ in the medium to continue adding ...
2 votes
1 answer
92 views

Does tropylium chloride exist in ionic form or does it exist as a covalent molecule?

My teacher taught me that in tropylium chloride, the chlorine atom posses negative charge to make the ring aromatic. I wonder that then will this compound will exist in ionic form due to very high ...
12 votes
1 answer
3k views

Why does a mixture of nitrous acid with concentrated nitric acid cause nitration of benzene instead of nitrosation?

A question came up in our worksheet to predict the reaction product of nitrous acid and concentrated nitric acid with benzene. I quickly recognized it to be similar to the nitration reaction. ...

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