56 Replies
,rotate
@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.this mechanism matches all the answers given in key
but why doesnt this work . ig this wont react further and thus leave question incompleted
,rotate
also in last rxn why doesnt epoxide open , forming this
Checking this wait
Mai claisen rearrangement bhool gaya lmao
I thought Claisen rearrangement was for allyl phenyl esters only. Huh.
The reaction that will undergo here is claisen as well
You can see there is an allyl "vinyl" ester out there
I'm almost done with drawing the scheme
(not the entire mechanism for now; can do that if @hardcoreisdead wants)
..
I think you've missed one thing
The H2SO4 is "dilute"
So the Cl would be kicked out by water
Forming a diol
And as it would be a geminal one... An aldehyde
Ohhh
Ek second
We have O negatives in the same molecule as well
This is a forced question uhh
There's no way those 2 Cl could stay as they are in the presence of dilute H2SO4
But if we don't assume that they stay as they are.....
The question doesn't make sense at all
There is no way that sulphuric acid step is gonna work like that
@hardcoreisdead
I think that second attack doesn't happen because of conformational reasons
There's that extra CH2 on that ring junction
That's the reason you're not able to draw this thing out respecting bond angles imo
Baaki I'll get back to you in a while if I find something on this
Yeah I guess overall the second ring 6 membered ring formation will cause the molecule to suffer a lot of strain due to the kind of confirmation it will adopt
the second image with 3 rings ?
so we can discard this out completely due to weird structure
See....
I just modelled this out
I checked the structure
Doesn't seem like something we can outright discard
So.....
I'm posting this on some other discord
I'll get back to you soon on this
alr
what bout this
I later thought about it
Realised the OH in the molecule itself
Could directly attack
And kick out the Cl
This is a mess uhhh
I'll see this again when I'm done and on this okayM
?
I'll come back in a bit
yeah yeah
btw this mechanism was given by my sir so i doubt kuch galat hoga
this too
Can you please keep this one aside for now
I’ll make sure to get back to you on this
This is giving me nightmares too so yeah
I’m also adamant to figure out what should happen here
I should probably take a look at this
That's what I thought too
Why do these people not use much of their brain while making questions like this
They don't even consider basic possibilities
The worst part about about jee organic: "the question framer doesn't care what actually happens and what doesn't
Well, Advanced is better on this front
They aren't too tbh
Just a moment did you consider the conformers of the product of the dil.H2SO4 reaction?
I've been seeing them ask shit for the last 2-3 years
Emphasis on 'better', not 'good'
Hmm I guess
Ahmm there's no need to I mean
That won't be a chair anyways
Double bonds on a cyclohexane
Why so?
That became an alcohol
There steric considerations
I mean once all the double bonds are gone
Yeah after that it's a chair
Then won't the attack of O onto the Cl- connected carbon be dependent on the position of the oxygen? It's too far to attack from an axial position I'm pretty sure
See that attack would happen only in a particular stereoconfiguration
But hydration is not stereospecific
Both possibilities will be formed
I'll see that once again
(Having dinner rn)
Once I get to the room
I'll draw out what I'm saying
This is the energy profile for cyclohexene btw
And as you can see, it's not a chair
(you can refer to clayden for explanation or maybe I can send a stack exchange answer)
This is where I get stuck
‘cause sabki chair conformation bana ke dekhni padegi
Moreover though, stereochemistry won't affect the attack on the Carbon with Cl much
@Opt
Ye I drew them out
Hmm
That won't lead us anywhere significant though
I just realised that
....
That's 'cause the attack is intramolecular which only depends upon the transition state being the less strained
Which can be made sure by just increasing ring size
Which is 6 and 7 here
So the cyclic transition state is also very stable
didnt read everything above
what was the conclusion?
We haven't reached any
oh
I'll ping you once we reach one dw
yeah
np
This question is going to go to bonus if this ever comes in jee imo
They'll have to consider both the possibilities
Baaki if one is slightly more favoured than the other
Idk
tbf the 3 ring product i made wont react further so doesnt that go out of question
That's like saying ki question aage diya hua hai
To aisa thodi hoga
That's not an apt reason to reject that possibility
aisa ho sakta hai
ban bhi rha hoga
but thats not of our concern
But how can we reject a whole possibility
You can reject it to reach the answer yes
The question setter wants you to do that
But I’m trying to find a valid reason as to why that possibility won’t be a major product
oh that ques makes sense
btw
did u reach a conclusion for this
can someone summerise whts going on here
We are kinda confused over this one
The question is very poorly framed
So we aren't sure of anything for now
Just considering possibilities
okk okk