Epoxide + grignard

[opaque anvil]

Problem 7
I first opened the epoxide ring from c=o wala carbon and then did reduction of the 😮 giving propan 1,2 diol

[ionic shoal]

<@&1227988359910260737>

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.

[heady plaza]

Epoxide?

That's a ester

Diester rather

[dusty plover]

We call such things lactones as far as I remember

Not that it matters

[golden oak]

,rotate

[heady plaza]

Yeah cyclic esters are lactones, cyclic amides are lactams.

But there's two ester groups here so

[golden oak]

well

[wild halo]

another doubt

[golden oak]

grignard attacks carbonyl, H3O protonates oxygen?

lemme try

[wild halo]

lets see if this one breaks us or not

[golden oak]

hopefully this one doesnt bring about doom clouds in the sky

[wild halo]

hopefully

[golden oak]

wait what does grignard do to esters

[dusty plover]

Considering it just shows one product....

[golden oak]

same C=O attack like aldehydes and ketones?

[dusty plover]

I guess it's gonna break us

[golden oak]

lmao

lets try

[golden oak]

@dusty plover?

[wild halo]

wait let me get my notes on grignard mechanism

[heady plaza]

Yeah

[heady plaza]

Yup, now attack the ketone

And protonate

[golden oak]

the lab record notebook goes hard

[dusty plover]

There's a methyl missing there I guess

[heady plaza]

This is the easiest hardcoreisdead doubt yet I think.

[dusty plover]

Ahmm I'll try but it seems like it won't break the way I've broken it

[heady plaza]

It will

[dusty plover]

The only rough page I had in my vicinity at this point lmao

[wild halo]

why did it get attached to the o with the single bond

[dusty plover]

Ahmm which one?

[wild halo]

see the mg br got attahced to the o which is in between 2 carbon

but why there?

[dusty plover]

'cause that's negatively charged

It's there to counter

[wild halo]

but doesnt grignard reagent attack the double bonded o

[heady plaza]

Sorry it's messy that's my brother's classwork

[dusty plover]

Lmao completely fine

I feel like it should be this
Haven't seen yours yet @heady plaza

Will see just now

[heady plaza]

Same

[dusty plover]

Yeah

Actually the simplest doubt bro has asked until now

[heady plaza]

Fr

[wild halo]

last night was too heavy for us

[dusty plover]

I was just under confident for the fact that I was feeling dumb a few mins ago for some reason

[wild halo]

opt wasnt there , otherwise it would have better

[dusty plover]

Fr lmao

[heady plaza]

I think I saw but looked at the clock and decided not to participate

[wild halo]

i think thts the effect of the que we did before this

[heady plaza]

Something like furan ring was there na?

[golden oak]

good choice

[wild halo]

yh it carried till 1:30 i think

[golden oak]

yes

[dusty plover]

Yeah not exactly though

[golden oak]

it wasnt even that hard though

like

not as much as we were making it out to be

[dusty plover]

It wasn't

[wild halo]

yhh sureeee

[golden oak]

i almost got it but i violated backbonding rules

[dusty plover]

I was stubborn ngl

[golden oak]

made a 6 ring instead of a 5

[wild halo]

we wrre overthinking a lot

[heady plaza]

As I said. Clock.

[golden oak]

this has to be the reason for sure

everyone's high on something in the late hours

but it was a fun time

[heady plaza]

I do not function like a human after 10pm

[golden oak]

i become more loopy and giggly than usual

[wild halo]

yh

[dusty plover]

I mean not exactly
I do stuff late at night but yeah I'm feeling kinda foggy for a day or two lmao

[golden oak]

early morning is just objectively better dawg

try it

[heady plaza]

My usual bedtime has been 8pm for the past 3/4 of a year

[golden oak]

as the sunrise hits your face and jolts you awake

goated

[heady plaza]

It changed like after BITSAT

[golden oak]

ok ive seen you regularly go to bed well after 8

[heady plaza]

I hit the sun in the face when he gets up

[dusty plover]

All I can say is..... I can neither sleep too late nor can I wake up too early

[golden oak]

12 hour sleep speedrun

[heady plaza]

By which you mean 1am to 6am or something?

[heady plaza]

I woke up at 9am todya

[golden oak]

no thats exactly what he cant do

[heady plaza]

After four missed calls

[golden oak]

F O U R ?

[dusty plover]

Yeah;(

[heady plaza]

One from mum

[golden oak]

cooked

[heady plaza]

Three from teachers

Asking me to check rank

[golden oak]

LMAOO

[wild halo]

lmao

[golden oak]

"advanced result advanced result WAKEUP WE WANNA PUTYOUONTHECOACHINGBANNER"

[wild halo]

this

[heady plaza]

@opaque anvil doubt solved? We're gonna chat too much otherwise.

[wild halo]

lekin why we talkin oh thread?

[heady plaza]

I won't be dw. Classmate got rank 390+ε

[golden oak]

i finally feel confident with fluids

[heady plaza]

Exactly

[wild halo]

me with equi

[heady plaza]

I want it to get closed

[golden oak]

only took god knows how many months

hell yeahh

[wild halo]

chalo zumdhal karna hai bye

[golden oak]

yes ok lets stop talking here

byebye

[dusty plover]

@opaque anvil either this one

[dusty plover]

Or this one

[opaque anvil]

in this portion double bond tut kar wapis double bond kaise bam gya

[dusty plover]

Vo actually maine 2 steps club kar diye

[opaque anvil]

Is it like this

[dusty plover]

Let me break it down ek second

No no

Wait

Pehle step me there's a mistake

Will send ek second

[opaque anvil]

ok so the way i formed pure cation at double bond was a big no no ?

[heady plaza]

Except in Friedel-Craft, yes

[dusty plover]

I mean… yeah I’d say that

[opaque anvil]

also jo second step mein O- bana hai uske electrons neeche kyu aaye . MgBr+ kyu nahi laga

wait a min

[dusty plover]

C=O ki bond energy is higher

Stabilises the whole structure

[opaque anvil]

whats the need of breaking that double bond

ill send my mechanism ek sec

[dusty plover]

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

[opaque anvil]

as the c=o wala c joint with o break a delta+ charge is created onto which Me- instantly attacks

[dusty plover]

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

[dusty plover]

(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+

[opaque anvil]

isnt breaking c-o bond much easier than c=o

[dusty plover]

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

[opaque anvil]

ohhh

that makes sense

[dusty plover]

You'll learn more about this dw

This is the interesting part of organic chemistry imo

[opaque anvil]

so pehle c=o tha , woh c-o- bana , again c=o and again c-o- which is then protonated to form c-oh

[dusty plover]

C=O and the various ways in which it can behave

[opaque anvil]

and this is happening at both the c=o simultaneously

[dusty plover]

Yeah exactly kyunki doosri baar me you didn't have a leaving group

[dusty plover]

Yeah you can say that

[dusty plover]

You got this?

[opaque anvil]

huh leaving group to dono time nahi hai

[opaque anvil]

why refrain tho

[opaque anvil]

acha

got this part

[dusty plover]

C-O vala bond toot raha hai
For that carbon the oxygen thing is a leaving group right

[opaque anvil]

i remember doing alcohol synthesis using carbonyl compounds

[dusty plover]

'cause grignard is not purely ionic

[opaque anvil]

and usmein aisa hi tha

[dusty plover]

Yeah so ye reason bataya basically maine tumhe uska

[dusty plover]

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?

@opaque anvil

[opaque anvil]

yeah written in my notes now

[dusty plover]

Nice

[opaque anvil]

+solved @dusty plover @heady plaza