92 Replies
one is obviously this
there are others which i cant figure out
@Dexter
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.A conjugated one could also form if this goes via E1 which isn't likely tbh as Ethoxide is a relatively stronger base
So that's kinda debatable
Ohhkaayy
So I gave it some thought
There will be only 2 products possible
One which you drew here
The other one is the hoffman one (when you take away H from the rightmost carbon)
no ,minimum 3 are possible
atleast acc to the key
This is what they must be forming
nah
But let me tell you
Which one then?
how is this even possible
dont wanna spoil the ques...
If you "somehow" get this kinda rearrangement via E1 mechanism
The driving force being the conjugation
Then you can get this one
According to me only 2 elimination products would be possible tbh
ig the two double bonds will do smthing fishy
hint: the other two products are cyclic
Except they won't
They "can't"
It would be an E2 reaction since the base is relatively strong
Other "two"?
So the hoffman one isn't even an option?
yeah
nope
it might form but unstable asf
only 2 alpha H
You said "possible"
Anything except the one you drew here is going to be "paper chemistry"
Nothing of that sort will form in the lab for sure
This is something I can think of
Complete ques
Multi correct ofc
Probably this is how you could explain one of those cyclic products
Yeah the cyclisation I drew works
one can do whatever he wishes in org chem š
why do we even do this
This question is shit
The maker hasn't ever visited an organic chemistry lab trust me
This would never fuckin happen in usual conditions
There must be some driving force
or we dont know the full story
I would have agreed if it was a six membered ring
Think by thermodynamics I'd say
A five membered....
Yeah it is stable
But not as stable so as to form out of nowhere
A six membered ring on the other hand has a negative formation enthalpy
So anywhere you could think of forming a six membered ring, it actually does form
guess only sir can clear this now
Hmm I guess
But as the question says "possible"
And you can see those cyclic molecules
You gotta form a carbocation somehow
And we have a leaving group
possible mein toh u can form 4 member ring too
but again unstable
That's not an option
Hone ko to I can somehow by some jargon show that conjugated vala product as well
lol fr
1/10 ques
The only problem with that one is that carbocations rearrange only if their stability increases at each step of rearrangement
'cause they don't have "future plans"
And in the conjugated case, I'll have to rearrange the carbocation two times without increasing it's stability before getting to the allylic one
So that doesn't make sense
Actually
Advanced organic questions have been very shit lately
They just do "anything"
Literally anything
IKRR
Doesn't happen in the lab?
We don't care
"critical thinking "
Btw
You understood this reasoning right?
But if you are asking something from an "experimental science" like chemistry, you can't do hypothetical stuff
exactly
There must be some evidence to back that up
anyways can u look at other doubt i posted
grignard one
Yeah I will just a sec
This one is solved I guess?
Ask anything else if you want
Although there's not much to say here
ill still keep it one
if someone brings a fresh perspective
Yeah sure thing
maybe ngp or smthing which we are overseeing
NGP is what I did though
yeah u didnt
Attacking in intra Molecular fashion
Huh?
NGPish
yeah
leave this for now
Hmm sure
i think b and d could be also there if it has 3 ans
Yeah we discussed that possibility above
This is how I think it should proceed @Sephrina
exactly wht i had in mind
Ngl doesn't make much sense to me
so we done here? is the doubt solved?
@hardcoreisdead wanted some fresh perspective
yh well i agree but out the options on these make a little sense
to happen in extreme conditions
which obvs isnt stated here smh
Hmm that's what I told him
The best I could do is see the options and see the "possible" products
yp
Not even extreme though
questions like this u have to choose the most possible ans and move on
You can't force "ring formation" using extreme conditions can you?
otherwise it u will give existential crisis
Yeah to solve questions, I guess but if you think about it, the question is shit
ofc it is
This is why I think it's shit
yp i read tht before
Ohh alright
Can you please check out that grignard question though
The same guy has posted above this one
yh hold on
That has taken away my sleep lmao
@hardcoreisdead we ok here?
Like I tried all possible combinations
Nothing works for that one
I guess he's either asleep or back to doing other questions lmao
mybe
Tried to sleep but couldn't lol
Looks like the only explanation is one given by varun
I just wanna know what's the limits
Heyya
Like here he shifted -ve charge mein from carbon 5 to carbon 1
Aise toh we can form basically anything
Naah we canāt
See the thing is
In reference to this
If we cyclise, the ring should be preferably a 5 or a 6 membered
āCause of ofc strain reasons
And when we see electrophile (carbon with a leaving group) and a nucleophile (the double bond) in the same molecule
There is a possibility that there will be an intra molecular attack
The possibility is very high in the case of a 6 membered ring
5 and 7 is kinda an overstatement but is possible
You get it now?
Yesh
Similar for 4 member
4 member would never form this way
You need some very strong nucleophile for that
You mustāve seen that SNngp reaction of halohydrins?
In which epoxides are formed?
Strained ringsā¦..but they formā¦.why?
ācause the nucleophile is too strong to ānotā attack
Alkene + x2 in h2o??
Yeah that one
Put some concentrated base afterwards
You get an epoxide
Doesn't that form cyclic halonium ion
Yeah that does, Iām talking about the next step
Oh
If the medium is basic
That OH can be deprotonated
Medium is neutral tho
X2 + h2o
I was talking about the one in basic mediumā¦..
Ahh
Add concentrated base either before hand
Or afterwards
Wouldnāt make much of a difference
Yeah afterwards a bit of epoxide could open up as well leading to the same product as the substrate
So itās preferred to keep the medium basic initially
I hope that was fine?
E1 honi chahiye
+solved @Varun_Arora
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