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.

Filter by
Sorted by
Tagged with
-4
votes
0answers
48 views

What will this compound be named [closed]

I found this structure on the cover page of my chemistry module and am very curious regarding what it will be named
1
vote
0answers
64 views

Why is 2-fluorobenzoic acid more acidic than 4-fluorobenzoic acid despite its intramolecular hydrogen bonding?

I was reading about $\mathrm{p}K_\mathrm{a}$ values of 2-fluorobenzoic acid and 4-fluorobenzoic acid and found that the latter had a higher value which was surprising to me. I think that ...
1
vote
0answers
31 views

Why is oxalic acid more acidic than benzoic acid?

I came across this fact while reading my book and was confused. Looking at the structures, I had the intuition that benzoic acid would be more acidic as the conjugate base formed will resonate all ...
6
votes
1answer
93 views

Why does Birch reduction of naphthalene with isoamyl alcohol form tetralin instead of 1,4-dihydrodialin (as formed with C2H5OH)?

I recently came across this question, which required me to know the difference between performing a Birch reduction on naphthalene using ethanol and using isopentanol. Why does using isopentanol lead ...
0
votes
1answer
49 views

Question regarding the colour of Benzoic acid and Benzyl alchohol

This question is primarily based on the Cannizzaro reaction, where a base induces a disproportionation reaction of non-enolizable aldehydes (benzaldehyde, formaldehyde, etc) to form an alcohol and a ...
-6
votes
2answers
124 views

what is an organic compound that can meet these conditions?

im looking for a gaseous substance (or airborne solid like dust) to use in my story that is organic, has a sweet odor, or at least pleasant enough to not cause any suspicion from main characters, is ...
5
votes
2answers
673 views

Why doesn't aromatic substitution add at multiple positions in one reaction?

When you do aromatic substitutions, you usually see the major products with one substituent added. My question is why can't you add multiple substituents in one reaction? For example, the image below ...
5
votes
1answer
94 views

Why is phenyl carbanion aromatic?

In phenyl carbanion, one carbon atom has a lone pair on it: This answer claims that the anion is aromatic, because "the lone pair on the benzene is in the plane of the ring and hence orthogonal ...
0
votes
0answers
29 views

Why is cyclopropenium aromatic but not cyclodecapentaene?

An $\ce{sp^2}$ hybridized carbon prefers a bond angle of $120^\ce{o}$. It would be willing to deviate if it acquires extra stability, for example through aromaticity. For this reason, the carbon atoms ...
-1
votes
0answers
51 views

Assigning priority to benzoyl groups

In naming the following compound; You choose the ring with the carboxylic acid because it has the higher preference than the benzoyl group, I presume. But I couldn't find the benzoyl group in any ...
-2
votes
0answers
18 views

Consequences of conjugation in Benzyl and Trityl Cations?

There are consequences of conjugation and I was wondering what the structural and energetic consequences would be when it comes to benzyl and trityl cations? I have spoke about how the bond length ...
-1
votes
1answer
35 views

can ozone run upwards through a silicon tube and exit against gravity?

I want to get ozone into an attic where rats are running around. For some reason, the attic is inaccessible to us. I ordered a bubbling ozone unit. We will drill a hole into the attic and run the ...
2
votes
1answer
61 views

Why is para-aminobenzoic acid more acidic than ortho-aminobenzoic acid?

Compare the acidic strength of o-, m-, p-aminobenzoic acids. I got that meta will be the most acidic as it won't be able to show R+ effect of $\ce{NH2}.$ But among the other two, i.e. ortho and para, ...
1
vote
1answer
78 views

Are phenyl and allyl groups in prop-2-enylbenzene coplanar?

Wouldn't C1 and C2 in prop-2-enylbenzene be on the same plane as that of the phenyl ring, right? If the double bond connected to C2 was between it and C1, they would be, but is it correct that now ...
8
votes
1answer
165 views

Why is quinone mono oxime more stable than 4-nitrosophenol?

When we do nitrosation of phenols, we get para-nitrosophenol as the major product, which tautomerises to quinone mono oxime. This article states that it largely exists in the quinonoid form. My ...
1
vote
1answer
68 views

How to identify the aromatic compound with the sum formula C7H6Cl2?

An aromatic compound (A), $\ce{C7H6Cl2}$, gives $\ce{AgCl}$ on boiling with alcoholic $\ce{AgNO3}$ solution and yields $\ce{C7H7OCl}$ on treatment with $\ce{NaOH}$. (A) on oxidation gives a mono-...
1
vote
1answer
56 views

What is the difference between resonance and π conjugation

I have seen electron delocalization mentioned frequently in 2 separate contexts: resonance (ozone, carbonate / nitrate...) and π-conjugation systems (aromatic compounds). While the 2 initially sound ...
2
votes
0answers
20 views

Which one out of a keto group or a hydroxyl group would get protonated first if both are present in a compound (attachment)

In the solution provided by my teacher he protonated the ketone, moved the +ve above by resonance did methyl shift and then did dehydration to form a benzene type system. Is this only because for this ...
2
votes
1answer
52 views

Numbering for the IUPAC name of this benzene derivative [duplicate]

My first guess was 2-chloro-4-nitrotoluene, but this was not among the choices for this question. My teacher says we will begin numbering from Cl, as halogens have higher priority than a nitro-group. ...
1
vote
0answers
27 views

Assigning carbon-13 NMR for ethyl 2-oxo-2H-chromen3-carboxylate

I have a molecule and an NMR spectrum, and I need to assign the NMR peaks to each of the carbons to the molecule: I know that the 14.19 ppm and the 61.94 ppm correspond respectively to the carbon 12 ...
3
votes
0answers
46 views

Comparing of melting point of dibromo p-xylenes

How to compare the melting points of the above isomers? I know that melting point depends upon the packing of the molecule, more efficient the packing, higher is the melting point. Symmetry in a ...
0
votes
0answers
57 views

Why is benzoic acid less soluble in water than acetanilide?

Why should acetanilide be more soluble in water than benzoic acid when benzoic acid has the same number of h-bonding sites and has an ionizable site, allowing it to form ion-dipole forces while ...
5
votes
1answer
155 views

Aromatic Character in Percentage?

I was just searching whether Uracil is aromatic or not and in this link$^1$ it is said that (from the abstract): High-level computational methods were tested for the enthalpy of hydrogenation of ...
1
vote
1answer
78 views

Aromaticity of Caffeine

In the Caffeine molecule, is aromaticity confined only to the 5 membered ring? The entire molecule is planar and the 6 membered ring also seems to have 6π electrons. The entire molecule has 10π ...
3
votes
2answers
91 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 6 electrons on p orbitals which could satisfy Hückel’s $n = 1,$ but the oxygen is sp3-hybridized....
7
votes
0answers
53 views

Mechanism of Hypervalent Iodine Phenolic Coupling

I need some help understanding the hypervalent iodine phenolic coupling reaction taking place in this synthesis of morphine, the reaction uses $\ce{PhI(OAc)2}$ as the hypervalent reagent and ...
2
votes
1answer
147 views

How can I synthesize 2‐amino‐3‐(chlorosulfonyl)benzoic acid from toluene or benzene?

I am trying to design a proper synthesis route for 2‐amino‐3‐(chlorosulfonyl)benzoic acid, though methyl 2‐amino‐3‐(chlorosulfonyl)benzoate—using an ester group in lieu of a carboxylic acid—would also ...
3
votes
0answers
63 views

Is azonine planar?

I came across aza[9]-annulene, which is given to be aromatic. I can clearly see it follows Hückel's rule with 8 π-electrons in the ring and the lone pair of nitrogen. But the thing that concerns me ...
1
vote
1answer
51 views

How to explain regioselectivity in nucleophilic aromatic substitution

I’m trying to rationalise the major regioisomeric product of the following reaction of an arylchloride in the presence of sodium amide: I have predicted that the para-substituted product is formed as ...
4
votes
0answers
50 views

Can bis-quaternary aromatic compounds act directly on acetylcholine receptors?

The book Cholinesterases and Anticholinesterase Agents gives examples of bis-quaternary aromatic compounds that are capable of inhibiting acetylcholinesterase. Page 400 gives examples of some such ...
2
votes
0answers
23 views

Reaction rate constants for the inhibition of cholinesterases by various carbamates

Darvesh et al. [1] have conducted a study on the anticholinesterase activity of various carbamates derived from phenothiazine. The authors measured the inhibition rate constants of rivastigmine for ...
3
votes
0answers
95 views

Introducing n-propyl group to benzene using cyclopropane

I am studying Friedel–Crafts alkylation reactions and my textbook states the following proposition [1, p. 1090]: Another very good means of introducing $n$-propyl group is to use cyclopropane as the ...
0
votes
1answer
87 views

Converting bromobenzene to 1‐bromo‐3‐methylbenzene

I started by taking $\ce{FeCl3}$ to reduce electron-giving capacity of $\ce{Br}.$ Then we need a methyl at meta, so I thought about Friedel–Crafts acylation, but then also methyl will come at para.
2
votes
1answer
38 views

Synthesizing 2-bromoaniline from bromobenzene

I am trying to synthesize 2-bromoaniline from bromobenzene. I came up with a reaction path, but I want your thoughts on whether this is feasible and can produce a decent yield. Sulfonation of ...
0
votes
0answers
25 views

Why is substituted amine a weaker activating group for electrophillic subsitution of benzene?

According to my text book the order of activating groups is as follows Why is it so ? shouldn't substituted amine have more +i effect and therefore should be a more powerful donating group ? Where am ...
0
votes
0answers
43 views

How come Cyclopropenylhydroxide exists and not cyclopropenol?

I'm currently studying aromatic compounds via online recorded lectures, and my teacher brought up about cyclopropenol and cyclopropenylhydroxide while teaching carbocylic non benzenoid compounds. He ...
8
votes
1answer
101 views

What's special about the purine scaffold?

Purine is a remarkable substance, given Nature has chosen it as the scaffold for two nucleobases from DNA/RNA: adenine (A) and guanine (G). Its structure also appears in several other substances of ...
1
vote
1answer
304 views

Decreasing order of electron density in benzene ring among the halobenzenes

What should be the order of electron density in monosubstituted halogen derivatives of benzene? I am aware that fluorobenzene is more ring activating as compared to chlorobenzene due to the more ...
1
vote
1answer
85 views

Why can't cyclohexylbenzene be called benzylcyclohexane? [closed]

The following structure represents the compound cyclohexylbenzene: Why can't the benzene ring be treated as a substituent and the compound be called benzylcyclohexane?
2
votes
1answer
53 views

Stability of pyridine derivatives

Arrange the following pyridine derivatives in the order of increasing stability of adduct formed with $\ce{BBr3}.$ Explain briefly. I'm pretty confused about which structure is the most stable. I'd ...
2
votes
1answer
211 views

Is a Methoxy group meta directing in this problem?

The following question was given in chemistry today , August 2020 edition , page 47 , problem 9. The answer to this problem is (a). My Attempt In the third step , the carbon electrophile can attack ...
1
vote
1answer
152 views

Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?

I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
1
vote
0answers
51 views

Why does benzene have only 2 resonance structures? Please answer keeping in mind I am in highschool [closed]

Why isn't this structure a part of resonating structures I can't upload the desired image so I will describe the structure. cyclohex 1,3 diene where carbon with numbering 2 has negative charge and ...
1
vote
1answer
78 views

What happens when FeF3 is reacted with benzene? [closed]

My text book says that halobenzenes can be prepared by aromatic substitution on benzene ring by using Fe or FeX3 as Lewis acid but this method isn't useful for preparation of fluoro benzene because of ...
3
votes
1answer
117 views

Nitration vs Nitrolysis

I am interested in nitrating an aromatic ester in a solution of dichloromethane. I found the following paper that describes creating a nitric acid solution in dichloromethane using KNO3 and sulfuric ...
-1
votes
1answer
140 views

Comparing acidic strength of ortho and para hydroxybenzoic acid [duplicate]

In orthohydroxybenzoic acid intramolecular forces operate which I believe tend to lock the position thereby making acidic H not available for release whereas in parahydroxybenzoic acid there in no ...
0
votes
1answer
136 views

Still struggling with Huckel rule and aromaticity [closed]

I'm still learning huckel rule and aromaticity in different compound. For the 1-methoxy-1,3,5,7-octatetraene, is it correct that it has 8 electrons inside the cycle, but since they will be 8, then it ...
0
votes
2answers
133 views

Aromaticity of different compounds

I'm new here and I'm still learning, I understand that there four rules for aromaticity: cyclic conjugated double bonding (every atom in the ring should be sp2) huckle number should be 2, 6, 10, 14, ...
-3
votes
1answer
115 views

Why aren't the pi electrons delocalized in cyclopropene?

I was searching on the internet whether cyclopropene is aromatic or not. I found out that the electrons are not delocalized, causing the molecule to be non-planar and so forth, a lot of reasons. But I ...
5
votes
6answers
858 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?

1
2 3 4 5
16