April 28, 2024, 01:23:22 PM
Forum Rules: Read This Before Posting


Topic: Aromatic Compounds  (Read 2745 times)

0 Members and 1 Guest are viewing this topic.

Offline AdiDex

  • Full Member
  • ****
  • Posts: 305
  • Mole Snacks: +16/-12
  • Gender: Male
Aromatic Compounds
« on: December 15, 2016, 03:11:31 AM »
Is it OK to say that every aromatic compound is some what less reactive and more stable ??  I've seen so much teachers who used to say this line that this is aromatic so must be stable .
But the thing that bugs me a lot , Let's take an example of Phenyl anion , it's has aromatic ring but again it's one of the least stable anion just because of the fact , the negative charge isn't delocalized .
Or say in case of Benzyne , it still has aromatic character but still , it's very reactive due to the fact of poor overlap of those two sp2 hybrid orbitals .
or the compound I've attached .

Offline mjc123

  • Chemist
  • Sr. Member
  • *
  • Posts: 2053
  • Mole Snacks: +296/-12
Re: Aromatic Compounds
« Reply #1 on: December 15, 2016, 04:42:02 AM »
Quote
Is it OK to say that every aromatic compound is some what less reactive and more stable ?? 
Less reactive and more stable than what? The statement on its own is meaningless. You always have to ask the question.
And yes of course, if a molecule has a benzene ring, but also has a very reactive group elsewhere in the molecule, the fact of having a benzene ring doesn't necessarily make that group less reactive. Why should it?

Offline AdiDex

  • Full Member
  • ****
  • Posts: 305
  • Mole Snacks: +16/-12
  • Gender: Male
Re: Aromatic Compounds
« Reply #2 on: December 15, 2016, 05:14:06 AM »

Quote
Is it OK to say that every aromatic compound is some what less reactive and more stable ??
- this is compared to non-aromatic molecules .

I was just pointing out that statement which is said by many teachers  . I was just wondering what should be the appropriate statement . Because I've seen a notion in many student's mind that Aromatic means stable .

Sorry ,I didn't put my post in a appropriate manner .



Offline mjc123

  • Chemist
  • Sr. Member
  • *
  • Posts: 2053
  • Mole Snacks: +296/-12
Re: Aromatic Compounds
« Reply #3 on: December 15, 2016, 08:33:47 AM »
I think it would be better to say that an aromatic compound is more stable than we would expect it to be on the basis of a conventional structure (drawn with conventional single and double bonds). Thus benzene is less reactive than we would expect for 1,3,5-cyclohexatriene, if it really had alternating single and double bonds. It doesn't undergo characteristic double bond reactions like addition of Br2, and although it can be hydrogenated, the heat of hydrogenation is less exothermic than we would expect for 3 normal double bonds.
It is not, however, more stable than a "non-aromatic" compound like cyclohexane. You have to be careful with your comparisons.
On the other hand, cyclobutadiene and cyclooctatetraene are not aromatic, and behave more like alkenes than arenes. You coukld say they are less stable than benzene.
The lone pair in phenyl anion, and the extra pi bond in benzyne, are orthogonal to the delocalised pi orbitals and to a first approximation do not affect their aromaticity.

Offline Vidya

  • Full Member
  • ****
  • Posts: 839
  • Mole Snacks: +46/-62
  • Gender: Female
  • Online Chemistry and Organic Chemistry tutor
    • Online Chemistry Tutor
Re: Aromatic Compounds
« Reply #4 on: December 15, 2016, 09:30:38 AM »
Is it OK to say that every aromatic compound is some what less reactive and more stable ?? 

More stable and less reactive is always in comparison to some other group ...like aromatic double bonds do not show addition reactions as shown by alkene double bond because they are more stable.More stable doesn't mean inert or non reactive.

Offline Enthalpy

  • Chemist
  • Sr. Member
  • *
  • Posts: 4041
  • Mole Snacks: +304/-59
Re: Aromatic Compounds
« Reply #5 on: December 15, 2016, 02:45:07 PM »
While the aromatic bonds themselves are strong, they have a differentiated effect on the nearby bonds.

kJ/mol
422 H-C3H7
400 H-C(CH3)3
472 H-C6H5
376 H-CH2C6H5
339 H-C(C6H5)3

So it wouldn't be the "compound" that is stable or nonreactive, but rather its aromatic ring(s).

This is for homolytic cleavage; ion stability too would see differentiated effects.

You can see similar effects with double bonds, carbonyls and so on:

kJ/mol
558 H-C≡CH
464 H-CH=CH2
369 H-CH2CH=CH2
321 H-CH(CH=CH2)2

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
Re: Aromatic Compounds
« Reply #6 on: December 16, 2016, 03:00:52 AM »
Is it OK to say that every aromatic compound is some what less reactive and more stable ??  I've seen so much teachers who used to say this line that this is aromatic so must be stable .

I think the point here is that, for example, a benzene ring is more stable than 3 isolated C=C bonds. Look up "Aromatic stabilisation energy" for further insight. It is not correct to say "every aromatic compound is some what less reactive and more stable".
My research: Google Scholar and Researchgate

Sponsored Links