Stack Exchange Network

Stack Exchange network consists of 175 Q&A communities including Stack Overflow, the largest, most trusted online community for developers to learn, share their knowledge, and build their careers.

Visit Stack Exchange

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.

1
vote
1answer
21 views

Consequences of ortho effect on resonance

Consider any carboxylic acid with any group at ortho position. According to ortho effect, the resonance of the $\ce{C=O}$ with the ring is inhibited. Is this resonance entirely lost? Or some little ...
5
votes
3answers
363 views

Why does the -OH group in β-naphthol direct the incoming diazonium salt towards the ortho position?

In the following reactions, the major product W is I was doing this question which asks me the product of a diazotisation coupling reaction between diazonium chloride and β-naphthol. I know ...
3
votes
0answers
22 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 sp2-hybridized and the molecule must ...
-1
votes
0answers
19 views

how to optimize the huckel stable structure for [16] annulene? [on hold]

It is well known that the geometry of [16] annulene is not planar. But when I am trying to optimize the structure in ORCA, I am getting the final geometry as planar. I have used the geometry with S4 ...
-1
votes
1answer
44 views

Identifying weaker base

Can you tell me the reason behind the answer to this: Which is the weaker base? (a) o-cresol; (b) Trifluoro-o-cresol. Answer: (b) trifluoro-o-cresol. I'm not a student in any institution. So ...
-2
votes
1answer
35 views

How can I add NO2 and NH2 opposite of each other on a benzene? [closed]

I know how to get one or the other on, but how do I get them both on? Here's what my starting and ending material look like:
1
vote
0answers
51 views

Does acetophenone show haloform reaction?

Although acetophenone is a methyl ketone, as it is aromatic, it is immiscible in H2O so the last step in the haloform reaction should not occur? I couldn't find any source regarding the haloform ...
3
votes
0answers
41 views

Can benzene undergo Diels–Alder reactions?

I was reading about the Diels–Alder reaction and wondered that since benzene also consists of two conjugated double bonds, then should it also undergo Diels–Alder reactions? If not, then why not?
1
vote
0answers
22 views

Aromaticity of Tropone [duplicate]

When we are determining if a given compound is aromatic using Hückel's rule, we count the number of delocalized $\pi$ electrons. In tropone for example, if I wanted to count the number of delocalized ...
0
votes
0answers
28 views

Organic conversion involving Grignard reagent and alkyl group with a carbonyl carbon on an benzene ring

I have been asked to synthesize the organic compound shown below using the following reagents and solvents. $\ce{Mg, Zn, Hg, FeBr3, AlCl3, Br2, LiAlH4, KMnO4}$, dil. $\ce{H2SO4}$, conc. $\ce{NH3}$, ...
-1
votes
1answer
44 views

Nitrobenzene - Aromatic Substitution Reactions

Which EAS (electrophilic aromatic substitution) reactions does nitrobenzene show? We know that nitrobenzene is particularly deactivated towards most such reactions, as the nitro group is strongly ...
-1
votes
1answer
26 views

Why is a compound that is more stable gives out less energy upon reaction? [closed]

I am having trouble relating stability with energy released. For example, I am looking at a statement regarding Benzene that says, since delocalised electron model of Benzene is more stable than the ...
14
votes
1answer
718 views

For a benzene shown in a skeletal structure, what does a substituent to the center of the ring mean? [duplicate]

I have seen diagrams with both the substituents attached to the benzene ring by the edges and other occasions directly to the delocalized ring. What does signify?
2
votes
0answers
31 views

How to Scan Aromatic Dihedrals To Obtain Force Field Parameters

I am trying to generate new force field parameters based on quantum mechanical calculation. I used amber manual "parameter development" title for this and I calculated bond-angle-non bond parameters ...
0
votes
0answers
22 views

Cyclic pent-diene + CHBr3 + t-BuOK. What is the product and how is it formed? [duplicate]

I think the answer is Bromo-Benzene but I am not sure. Please also provide the mechanism as to how the product is obtained.
2
votes
0answers
44 views

Is there a way to form only ortho product without using fractional distillation?

Using benzene and ethane as your only source of carbon in the final molecule, synthesize the following using any useful reagents. Reaction must form pure ortho compound. I have to form the ...
2
votes
2answers
47 views

Why is it aqueous and ethanolic conditions for nucleophillc substitution of cyanide ion with benzyl chloride?

I was doing an exam question where benzyl chloride was undergoing a nucleophilic substitution with cyanide ion to form benzyl cyanide. Please can someone enlighten me as I have never seen both ...
3
votes
0answers
47 views

Mechanism for the addition of chlorine to benzene to form hexachlorocyclohexane

I am familiar with electrophilic substitutions of benzene, with chlorine using a halogen carrier catalyst such as $\ce{AlCl3}$, to produce chlorobenzene, and I am aware of the mechanism. But, ...
0
votes
1answer
46 views

Oxidation of 2-Methyl, 2-Phenyl Propane

Considering oxidation mechanism of side-chains in arenes, it is known that side-chains get oxidized to carboxylic group ($-COOH$). Below is a picture of 2-Methyl, 2-Phenyl Propane. When it gets ...
1
vote
0answers
36 views

Find the increasing order of formation of ortho product

Find the increasing order of ortho product formation when Y is (i) F, (ii) Cl, (iii) Br, (iv) I. We know that halides are ortho, para directing for EAS reactions and we consider the electronic ...
6
votes
1answer
76 views

Mechanism of oxidative dearomatisation with hypervalent iodine

The following step was taken from the synthesis of Kinamycin C on SynArchive. It employs the use of a peculiar reagent, that is, bis(acetoxy)iodobenzene (BAIB), also known as phenyliodine(III) ...
0
votes
0answers
57 views

Why is phenol less basic than aniline in acidic medium? [duplicate]

In acidic medium aniline is m-directing because of protonation of $\ce{NH2}$ group. But why doesn't the same happen in case of phenol, why is phenol an extremely weaker base as compared to aniline?
0
votes
0answers
24 views

Reactivity order of different (alkyl/acyl) halides towards Friedel Crafts reaction?

In Jerry March, in the section discussing the Friedel Crafts reaction, it is mentioned that for the Friedel Crafts Alkylation reaction, the reactivity order of the alkyl halide is (usually) R-F > R-Cl ...
4
votes
1answer
57 views

Partial oxidation of toluene

While reading the preparation of phenol from cumene by reaction with $\ce{H2O2}$ or partial oxidation, I was curious to find out why toluene wasn't used. I checked the literature and found that ...
3
votes
1answer
79 views

Which is easier, the nitration of toluene or the nitration of mesitylene (1,3,5-trimethylbenzene)?

Does the toluene can undergo nitration easier than mesitylene (1,3,5-trimethylbenzene), due to the high repulsion that will occur between $\ce{NO2}$ and the two adjacent methyl groups (in mesitylene ...
1
vote
0answers
33 views

How is a ring formed when a carbon atom in an aliphatic chain attached to benzene ring has a positive charge?

This is my approach towards this problem. First off, a positive charge would appear in the C atom at the end of the chain, and then that carbocation would rearrange into a tertiary carbocation. But I ...
1
vote
1answer
60 views

Kb values of N,N-dimethylaniline derivatives [closed]

I need the $K_\mathrm{b}$ values for ortho-, meta- and para- positions of the following compounds: I've looked and couldn't find them anywhere.
2
votes
0answers
25 views

Isoptope effect on electrophilic aromatic substitution

My book reads Sulphonation will be the most effected electrophilic aromatic substitution reaction when benzene is replaced by hexadeutrobenzene. I am not able to figure out how. All EAS reactions ...
2
votes
0answers
20 views

More stable carbocation, tertiary or benzylic? [duplicate]

This is a very confusing question that which is more stable, benzylic or tertiary butyl carbocation? Some sources say benzylic due to resonance some say tertiary due to +i effect and 9 ...
4
votes
0answers
44 views

Standard abbreviations for polycyclic aromatic hydrocarbons, similar to those for nucleic and amino acids?

The Nature paper Characterizing particulate polycyclic aromatic hydrocarbon emissions from diesel vehicles using a portable emissions measurement system addresses polycyclic aromatic hydrocarbons (p-...
2
votes
0answers
80 views

Kinetic and thermodynamic control of sulphonation of toluene

Sulfonation of toluene with conc. $\ce{H2SO4}$ at room temperature gives ortho- and para-toluenesulphonic acid (with $95 \%$ yield), whereas sulfonation of toluene with conc. $\ce{H2SO4}$ at $\pu{150-...
4
votes
1answer
88 views

How to draw protonated benzene (horseshoe) carbocation structure with ChemDraw?

Is there a way to draw the aromatic "horseshoe" (forgot the official name) structure of a protonated benzene cation (arenium) with ChemDraw, and not the cation with double bonds?
0
votes
1answer
30 views

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?
1
vote
1answer
32 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 ...
1
vote
1answer
40 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 ...
6
votes
1answer
166 views

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 ...
0
votes
0answers
76 views

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 ...
0
votes
0answers
29 views

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 ...
1
vote
1answer
96 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 ...
0
votes
0answers
31 views

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 ...
1
vote
0answers
34 views

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 $\pi$-...
1
vote
0answers
77 views

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 ...
0
votes
0answers
59 views

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 ...
-4
votes
1answer
61 views

Question about the cyclic hemiacetal form of compounds [closed]

Why is D not a valid answer for this question?
2
votes
0answers
228 views

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 ...
1
vote
1answer
58 views

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. ...
0
votes
2answers
80 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 ...
1
vote
0answers
36 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 ...
2
votes
1answer
88 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 ...
1
vote
0answers
40 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 ...