Aromatic vs ring strain

I was under the impression ring strain would matter more but they haven't considered that at all
No description
17 Replies
iTeachChem Helper
@Dexter
iTeachChem Helper
Note for OP
+solved @user1 @user2... to close the thread when your doubt is solved. Mention the users who helped you solve the doubt. This will be added to their stats.
Nimboi
NimboiOP6d ago
should i just ignore ring strain, and why
Real potato
Real potato6d ago
Because in this case ring 1 isnt aromatic but ring 2 is Thats why we will consider ring 2 to be more stable
Nimboi
NimboiOP6d ago
i know that but when should i consider ring strain, if at all bond angle strain
Gamertug
Gamertug6d ago
inst that dancing resonance or am i wrong
Opt
Opt6d ago
Ring strain exists when sp³ carbons have bond pairs closer to one another than the optimal 109°28'. But, you see, there are no sp³ carbons here in the second structure in the first place. The entire thing is planar, and the continuous delocalisation further stabilises it.
Gamertug
Gamertug6d ago
i think i am wrong
Opt
Opt6d ago
It's not. That's for cyclopropylmethyl carbocation
Nimboi
NimboiOP6d ago
wrong ping is there uhh logic to that the logic i used for ring strain was simply that the bond pair electrons were too close at a smaller angle
Opt
Opt6d ago
Frack, I clicked the first one that popped up. It went by recent order ig.
Nimboi
NimboiOP6d ago
happens
Opt
Opt6d ago
Well, yeah, there is a considerable difference between 120° and 60°, but the resonance should take care of that.
Nimboi
NimboiOP6d ago
oh alright then is ring strain a prevalent effect at all? i want to know where it stands in strength compared to other effects
Opt
Opt6d ago
Right there with any other steric hindrances. In cases where you have substitutions or additions via an intermediate, keep an eye out for rearrangements, but if the intermediate is in resonance, neglect. In case of elimination, resonance is gonna try to force itself into the product as much as it can. If it can't, it's probably a single step elimination and no chance of any kind of rearrangement. It's just another kind of steric inhibition. Might slow down addition at certain centres, too, but that's about it I think.
Nimboi
NimboiOP6d ago
ah, okay that clarifies things thank you +solved @Opt
iTeachChem Helper
Post locked and archived successfully!
Archived by
<@717724055217635398> (717724055217635398)
Time
<t:1737028365:R>
Solved by
<@763645886500175892> (763645886500175892)

Did you find this page helpful?