332 Replies
O(18) refers to isotope of oxygen
@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.Yeah sir first protonate the alcohol
Why?
'cause the lone pairs of that epoxide are not "localised"
That's a hint
Try to proceed from there
ohhhh the lone pair of o18 in resonance
big brain
R-OH in presence of H+ becomes carbonyl ???
Not necessarily
But it could be depending upon the substrate
basically can H+ oxidise alcohol
Not on it's own imo
alr
There must either be something on the substrate or something with the reagent that can be reduced
Ofc electrons won't fall from heaven:)
in the OH one right?
i thought in terms of dehydration and started by removing oh and then ring expansion of 5 member ring
and then looked at the ans
dono cheezein galat kari
Ahmm really?
Did you do it wrong ya idea hi galat tha?
Yup
I didn't use pen paper for this yet
I guess I really should now
idea hi galat
Huh weird
yh ill try too
could it be that double bond undergoes catalytic hydration and becomes oh
and then pinacol pinacolone
But that's not something that's prioritised
Carbon oxygen bond is much more polarised already
i dont think no shift will be here because its a 3 degree carbocation
Oxygen of the alcohol has shit ton of electron density
so removal of oh is prioritised over breaking double bond?
Think in terms of polarisation
ys because h2o is good leaving group
And yahan to intermediate bhi stable hai btw
O has lone pair
omg my way gives the correct ans
😭
why tho
Not necessarily because of that
Baad me bhi stable intermediate ban Raha hai
I'll scribble a bit myself wait
3 degree ys
Bhai @hardcoreisdead saare ajeeb questions tere paas hi kyun aate hain?
courtesy of aakash invictus module
they cooked real hard in a span of months
Aaah aakash
Brings back memories
aakash modules are pure bs
jan mein fiitjee choda sabne and they cooked up this abomination
not the invictus ones
full of question whose solutions make no sense
Plus One tbh
invictus aakash is diff from aakash iitjee
Ahmm I see
the question bank has que on topics tht was in sylllabus in like 2008
official launch in feb or march 2025 ig
idk i have the neet one
oh
anyways
back to the question
mine is way older
ohh
are there any other reactant present rather than these in que or?
could it be that 5 member ring is more stable than 4 isliye pinacol hua
nope yhi ques hai
also oh protonate karke jo carbocation banega can it even undergo ring expansion
ek taraf double bond hai and dusri taraf C-O bond
ok
tht has a double bond though the 5 C ring
if pinacol wale se dekhe toh woh toh tut jayega
this yh
Protonating that OH seems like a dead end
I'll think about this and post in a bit
what if the H+ goes to the o 18 ?
because defs it will behave slightly diffrent than the O16 atom
Different in what sense though?
Resonance to same hi fashion me hogi na?
i think the O 18 lone pair would prefer to be in reso
Yeah that's what we concluded above as well
She was saying if the O being 18 makes a difference
ah
well okay
suppose we protonate the OH
becomes H2O
leaves
Then that's a dead end
creates carbocation at the ring bond bridge
double bond resonates to the C+?
moves the C+ charge?
ring expansion?
That's what I'm confused about
Could go on to form a 6 membered ring by expansion
I'm still working out on this
alr alr
Hopefully ho jaaye
what other alternatives are you considering?
mechanism wise
See for now I've crossed out possibilities for things like methyl and hydride shifts
oh huh yeah i prolly should have considered that
Maybe do that but I didn't find anything that could stabilise the cation more
Neither was that thing kinetically favoured
If you notice something, then post it here
Question seems good
sure 👍
wait but thermodynamically
if i have my concepts right
the 6 membered ring should form right
its a slow product but its the most stable one yes?
Yeah that is why I was considering it
oh but the problem with trying to ring expand after the C+ rearrangement is
the double bond has gone into the bridge of the 4 and 5 ring
can a carbon just detach from there and pursue the C+ cation?
that would leave a C+ on an sp2 carbon
Ahmm I cannot really visualise
Can you please send what you're drawing out?
The way I did it, I didn't see anything of that sort
That can't happen I can guarantee
ok yh nvm i realised what i was thinking was with a double bond of O i got the structure wrong sorry
At least not in the usual condition
Not a problem happens
And now I'm stuck with something completely different lmao
Will watch over this in a few minutes
yeah nvm im wrong then
yh no i dont have any idea over this que now
💀
this is one hell of a good que
real lmao
@Varun_Arora maybe its a markovnikov like mechanism and the H+ goes to the less substituted side of the double bond, leaving a stable tertiary carbocation also stabilized by O18 resonance?
upon which maybe then ring expansion happens
4 to 5 type
See the reason I'm not considering the double bond is because there is a better and more suited site for protonation
ah yeah fair
But as it leads me to a dead end, I might consider your thing in the end as well
this carbocation seems really stable though
yeah
I'm starting this from scratch bhaad me jaaye
💀 😭
I just got done with something else I was trying to figure
Game on now 🔥
motibhation chain
there are resonance so yh i agree
moti behen padhi mai isse
lagta hai tumhe neend aa rhi sojao 💀
nhi nhi vo faltu assignment likha na dimag off ho gya hai
abhi chem karti thoda que khulega dimag
accidentally made a 7 membered ring trying to solve this
im high asf
how did u make 7
6 ok
7?
thats illegal yes 😭
u need rest
kwestion interesting lage
fr
kwestion majedrr hai
did u guys get smthing ?
does the answer have 1 five and 1 six membered ring attached to each other
if yes then maybe im getting somewhere
if no then idek
nope
cooked
anyway my thought process had an oxygen with a positive charge
not happening
i believe the double bond breaks giving a carbocation which is backbonding stabilised. this will cause the ring expansion of the five membered ring
so two five membered rings joing together
are you talking about the carbocation that ends up next to the oxygen on the tertiary spot
the reason Varun doesn't think that happens is because OH is simply more of a suitable site for protonation and thus water to escape
but we dont seem to be getting anywhere with that
?
yeh wala
yes that
i thought
it would rearrange (hydride shift) upwards
so that the ring expansion could be 6 membered instead
oh han yeh baat bhi theek hai
when we get a ans pls ping me too
@hardcoreisdead @Sephrina my thought process
im not sure if this is the correct way to think about it ofc
we'll wait for Varun to pop back in
hello sans
Expansion is possible after rearrangement?
i dont see why not
unless i missed something
Nooooo
Back bonding is already there on step 2 why would it rearrange
hm
6-ring instead of 5-ring?
idk which takes more priority under thermodynamic control
Backbonding>resonance
3 deg se 2 deg pe kaise rearrange hua
that's the step im hesitant about yes
but perhaps under thermodynamic control
the most stable product is the 6 membered ring
i dont know maybe
I don't think so tbh
6 membered rings are stable beacuse of some other non reso related reason right
that's why ring expansions happen even in non conjugated systems
Yeah but the rearrangement
i know it looks dodgy
6 membered rings have negative formation enthalpy
Yes but like it rearranges then expands
That's the reason
Not expands
O is giving lp
@Varun_Arora review mechanism above?
But yeah it won't do that expansion at the cost of taking away back bonding
Yeah I kinda did
ah oke oke
I have the same ick as @sans
that's confusing how do we know that
I'll try once but prob won't get one sec
Yaar this shit is weird
why is it that half of hardcoreisdead's doubts give me an existential crisis
There's so much to consider
to be honest at this point this question is questioning my existance i am out till morning
All of them give me one
omg THIS
good idea lmao
And I am already in college
hardcore nga gonna score single digit rank
Riyal
and i hvnt even done half of syllabus and these questions scare me to do it
fr
Fr
I'm done
Ain't sleeping until I'm done with this shit
dawg 😭 you'll develop a much better intuition for orgo with time
dont worry
go ahead synthesize it in the lab to see what happens >:)
True it takes a lot of time If say
i will probs check at 2 cuz i will take a break tht time if its done do tell me
dude yeah it took me multiple months
to get to where i am now
i hope
Lmao
Prolly would do that if I have some PhD convinced 💀🙏
I'll surely tag all of you guys dw
new doctorate idea confirmed
to be honest all knowledge i have is from feb this yr no bs my 11th is wsted
Can expansion happen here or nah@Varun_Arora
yes i will also go sleep now
thnks
not like i learnt organic in 11th either
gnite boiz and gurlz
Gn
i didnt do any of the sub
expansion here gives a positive charge on the sp2 carbon
which varun said no to
i had the same idea
double bond shift?
First that's just a resonance structure
Yeah that's what I was thinking also
Exactly
Yeah I'm just trying out stuff
should we ask vader for inputs his organic was fire
I mean it's not 'cause I said
You can really think about it (sp2 pe positive doesn't make any sense)
but alright 😭
though im not sure he is active much
no no i understand hahah that's why i questioned it too
Ask him maybe
but you probably just have a better intuition than i do
Can't it just rind expand without rearrangement......
no
I mean depends
sry 5>4
Naah it can you're correct but in this case that leads you to a dead end
@LordVaderAni can u help out in this que.
copy pasting again it is way upp
WHY CAN'T I FIGURE THIS OUT!
calm down
take a break
Fr I should lol
and come over again
@Varun_Arora @Sephrina
What about this
Back bonding 4 ring to backbonding 5 ring
Better no
Yeah see this is something we can do but the OH is a better site for protonation
We already were here previously
it seems good to me
No if the h+ is dilute
This happens
If it's concentrated
Then dehydration
H+ is primarily an acid
So it better behaves as a protonation site
No like double vond and dil h+ gives sn1
conc protonates I think
That's not as polarised
its almost this
suppose it is a better protonation site, if it leads to a dead end then in the thermodynamically controlled product does it matter? then the H+ will go to the double bond right
I honestly don't know about polarisbility
ik it is bizzare to say but can there be functional grp shift?
only diff in given ans is that o18 and c=o are on opposite ends
just a random thought
bruh what
😭😭
wht
ok nah i call cap what
Show mechanism
Functional groups can't shift as far as I know
i just had a thought i didnt try
I guess we should all once try this from scratch
thts why i am asking is it possible
Like all of us
How did the other oxygen get inside the ring BRUH
yh
How tf man
Yeah I just told you
Good thing I don't have to deal w ts anymore
Ohh you're done with jee and stuff lmao
no i think we're nearly there
Mhm
no rearrangement of C+ cation to tertiary spot though?
with oxygen backbonding?
Except we aren't
yeh dia hai ans
I didn't rearrange
This was my answer
Right
your was kinda cis
where?
yeah it is innit
No mine was
This
like neeche tha c=o instead of up
for some reason the spatial orientation is different
Bro
it ws inverted
Bruh I'm turning off discord for some time lmao
It's the same thing BRUH
no we got it bro fr 😭
sans got the answer
ITS THE SAME THING I CAN EXPAND DOWN
no not really since the rings arent rotating
due to angle strain
(ig)
bro....
ykw
table flip ahh chemistry doubt thread
(╯°□°)╯︵ ┻━┻
(╯°□°)╯︵ ┻━┻
Hold up
I'll come back in a bit guys
I wanna cry and start again
we broke varun
great job guys
ill go too
lmfao
@sans good job dawg
i think you got it
i probably will be able to do eqi after this
nearly if not exact
if not u guys are the blame
warm up tha tumhare liye
icic
why doesnt c=o being up and down not make a diff
There u go
It's up now
ig the rings are rotating then
LMAOOO
LMFAO
they probably exist as 50% up 50% down
this is so fucking iconic
the scribbled "there it is. its up now."
i want to pin this thread
bro
what a legendary moment
😭😭
nahi ig woh beech wale carbon ke about rings are constantly rotating so upar neeche kuch bhi ho sakta hai
ikr
no no see
up and down have
slightly different mechanisms
i dont think the bond rotates
but its a 50/50 chance whether 1 given reaction makes up or down
Bro ur still not getting it 😭😭
look at the mech again
its not rotation
They're perpendicular IT DOESNT MATTER
it just has an enantiomer that's all
han whi toh kaha meine bhi
good job guys we agree
so jao ab
will keep it open
Not sleepy
yeh
in case someone (varun) needs to rant
or smthing
🥀
how funny would it be if he woke up and dropped an entirely new valid mechanism tomorrow
hes gonna cook hard tonight
"it occured to me in a dream" ahh chemistry
frfr
ramanujan but chem
I genuinely thought what he meant was both the o18 and normal o were swapped in the answer
yeah my instant reaction to that was "no way, that's a typo"
Yeah if any of you are awake rn….
Mhm
This is what I conclude
If this matches exactly with somebody else’s, then I completely agree with that
I got most probable product
.
Yeah that should be it ‘cause protonating the OH doesn’t take us anywhere
There’s no particularly “stable” intermediates we could form after that
Sorry for being so stubborn about not protonating the double bond earlier
It's alright bro I don't even have chem no more
😭
I kinda had my biases ‘cause I’ve always seen the OH being protonated more so and it also makes much more sense ‘cause that bond is a lot more polarised and probable to break
Lmao
I kinda get sentimental with chem sometimes
What i was taught was dilute h+ is double bond to alc and concentrated is dehydration
Bruh lol
That thing anyways doesn’t guarantee but yeah you can think of it like that
Just the thing is that in dilute conditions, you don’t have much H+ to protonate but a lot of water to attack the double bond
u GUYS STILL HERE
Water doesn’t assist in protonation directly rather it just polarises the bonds more
Because of which when we do thing in concentrated H2SO4, we get dehydration product as that alkene is no more “much susceptible” to Polarisation by water
Yuh
I just came here
😉
dont you all sleep
who says
me who sleeps at 3
Bro imma be real with u I can't be bothered bc it's over 😭😭
Sorry
I sleep at 4
💪💪
suabh kaam rhta hai itna late nhi kar sakti
For the past few days…. Not much ‘cause @hardcoreisdead brings up really good stuff for me to ponder about
but didn't u say sleeping late is rlly bad @Sephrina
ikr
Hypocrisy
im a hypocrit
Not a problem bro lol
That could help others so I just wrote that
fr
i study on sleep and its cycle and its importance
but i sleep at 3 myself
I just cant sleep bro I'm so free I couldn't care less
ruining my memory
Good job
I had brainfog for months
nights are peaceful
get atlast 6hrs u should be fine ig
Yaar you guys prepping should sleep early c’mon 😭
REAL
i can do zumdhal easy at night
i do like 10h
Bro nowadays my dad isn't sleeping at night it's so annoying
I'm not alone
What’s that uh
Some book?
should we? ys do we? no
you sleep till like 1pm?
up organic
Nicee
no '
naps at afternoon
that's 10hours
Ohh never heard of that ngl
Ahh
i wake at 9 or 10
awesome book
Naps more like 5hrs nap
😭😭
it is carrying my whole of chm rn
I used it for electrochem
We be discussing general chat stuff on hardcore thread
bro tht stuff is nasty
true
Chem is actually really fun with the right stuff
Nahhh wdym
It was easy
Damn that’s nice
Maybe bc I did harder books
i cant do log so im bad at it
The problem is with the way it’s taught
Not the subject
I mean
Wdym u can't do log smh
this
Don’t teach the stuff you can’t explain so early on
Yuh
i suck at math
Let’s move to general guys 😭
i had 96% in boards so not tht bad but ys i suck at it
Log values shouldn't be stopping u tho
just remember them bruhh
😭😭
Hardcore gonna be pissed in the morning not seeing answers but this
Woahh
Shiver me timbers
😈😈
@hardcoreisdead
Just for you bro
This is what we have concluded
me being mod and doing stupid stuff
bro cooked hard
+solved @Varun_Arora @sans
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