Epoxide + grignard
Problem 7
I first opened the epoxide ring from c=o wala carbon and then did reduction of the 😮 giving propan 1,2 diol
128 Replies
@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.Epoxide?
That's a ester
Diester rather
We call such things lactones as far as I remember
Not that it matters
,rotate
Yeah cyclic esters are lactones, cyclic amides are lactams.
But there's two ester groups here so
well
another doubt
grignard attacks carbonyl, H3O protonates oxygen?
lemme try
lets see if this one breaks us or not
hopefully this one doesnt bring about doom clouds in the sky
hopefully
wait what does grignard do to esters
Considering it just shows one product....
same C=O attack like aldehydes and ketones?
I guess it's gonna break us
lmao
lets try
@Varun_Arora?
wait let me get my notes on grignard mechanism
Yeah
Yup, now attack the ketone
And protonate
the lab record notebook goes hard
There's a methyl missing there I guess
This is the easiest hardcoreisdead doubt yet I think.
Ahmm I'll try but it seems like it won't break the way I've broken it
It will
The only rough page I had in my vicinity at this point lmao
why did it get attached to the o with the single bond
Ahmm which one?
see the mg br got attahced to the o which is in between 2 carbon
but why there?
'cause that's negatively charged
It's there to counter
but doesnt grignard reagent attack the double bonded o
Sorry it's messy that's my brother's classwork
Lmao completely fine
I feel like it should be this
Haven't seen yours yet @Opt
Will see just now
Same
Yeah
Actually the simplest doubt bro has asked until now
Fr
last night was too heavy for us
I was just under confident for the fact that I was feeling dumb a few mins ago for some reason
opt wasnt there , otherwise it would have better
Fr lmao
I think I saw but looked at the clock and decided not to participate
i think thts the effect of the que we did before this
Something like furan ring was there na?
good choice
yh it carried till 1:30 i think
yes
Yeah not exactly though
it wasnt even that hard though
like
not as much as we were making it out to be
It wasn't
yhh sureeee
i almost got it but i violated backbonding rules
I was stubborn ngl
made a 6 ring instead of a 5
we wrre overthinking a lot
As I said. Clock.
this has to be the reason for sure
everyone's high on something in the late hours
but it was a fun time
I do not function like a human after 10pm
i become more loopy and giggly than usual
yh
I mean not exactly
I do stuff late at night but yeah I'm feeling kinda foggy for a day or two lmao
early morning is just objectively better dawg
try it
My usual bedtime has been 8pm for the past 3/4 of a year
as the sunrise hits your face and jolts you awake
goated
It changed like after BITSAT
ok ive seen you regularly go to bed well after 8
I hit the sun in the face when he gets up
All I can say is..... I can neither sleep too late nor can I wake up too early
12 hour sleep speedrun
By which you mean 1am to 6am or something?
I woke up at 9am todya
no thats exactly what he cant do
After four missed calls
F O U R ?
Yeah;(
One from mum
cooked
Three from teachers
Asking me to check rank
LMAOO
lmao
"advanced result advanced result WAKEUP WE WANNA PUTYOUONTHECOACHINGBANNER"
this
@hardcoreisdead doubt solved? We're gonna chat too much otherwise.
lekin why we talkin oh thread?
I won't be dw. Classmate got rank 390+ε
i finally feel confident with fluids
Exactly
me with equi
I want it to get closed
only took god knows how many months
hell yeahh
chalo zumdhal karna hai bye
yes ok lets stop talking here
byebye
@hardcoreisdead either this one
Or this one
in this portion double bond tut kar wapis double bond kaise bam gya
Vo actually maine 2 steps club kar diye
Is it like this
Let me break it down ek second
No no
Wait
Pehle step me there's a mistake
Will send ek second
ok so the way i formed pure cation at double bond was a big no no ?
Except in Friedel-Craft, yes
I mean… yeah I’d say that
also jo second step mein O- bana hai uske electrons neeche kyu aaye . MgBr+ kyu nahi laga
wait a min
C=O ki bond energy is higher
Stabilises the whole structure
whats the need of breaking that double bond
ill send my mechanism ek sec
This is something you’ll study in detail in aldehydes and ketones
Idk why would they put this before that
Aakash people are so fuckin dumb
as the c=o wala c joint with o break a delta+ charge is created onto which Me- instantly attacks
See the reason why we break C=O is because it's much more polarised
You'd agree on that right?
And afterwards, as there is a leaving group on the carbon of C=O
(which was C=O before)
The electrons act nucleophilically
To kick out that leaving group
Does that make sense?
And btw refrain from showing Me- as something separate from MgBr+
isnt breaking c-o bond much easier than c=o
Breaking the pi bond is much easier
'cause it's already much more polarised
Imagine Oxygen pulling electron density just via one bond
Now it's 2
C "double bond" O
ohhh
that makes sense
You'll learn more about this dw
This is the interesting part of organic chemistry imo
so pehle c=o tha , woh c-o- bana , again c=o and again c-o- which is then protonated to form c-oh
C=O and the various ways in which it can behave
and this is happening at both the c=o simultaneously
Yeah exactly kyunki doosri baar me you didn't have a leaving group
Yeah you can say that
You got this?
huh leaving group to dono time nahi hai
why refrain tho
acha
got this part
C-O vala bond toot raha hai
For that carbon the oxygen thing is a leaving group right
i remember doing alcohol synthesis using carbonyl compounds
'cause grignard is not purely ionic
and usmein aisa hi tha
Yeah so ye reason bataya basically maine tumhe uska
As a whole attack karta hai and that MgBr+ thing attacks the negatively charged oxygen simultaneously as Me- attacks C=O
Same thing happens with R--Li kind of compounds
(Organolithium as we call them)
Got it?
@hardcoreisdead
yeah written in my notes now
Nice
+solved @Varun_Arora @Opt
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