Stereoisomers
How many different triols would be formed when given compound is treated with excess ch3 MgBr followed by hydrolysis
72 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.What's the compound?
Posting
I guess the photo didn't go through
Shit I don't have pen paper rn 😭
Is the answer 4?
Nope
Kind of a guess
Maybe I'll have to draw it all alright
Will see this later when I have access to pen paper or my tab 🙂
Alrr
Is the answer 8?
My approach
Although I might be wrong
Also the chiral carbon at position 2 from the left
So 4 times 2 would be 8 ig.
Oh wait its configuration is fixed, sorry :/
Yeah:)
I do think it should be 4 only @hardcoreisdead @SirLancelotDuLac
@Opt
Your perspective?
yus
ans key mei bhi 8 hai
and no one has objected up until now
How does 8 make sense though?
To me it doesn’t
Maybe I’m missing something
i found this
if it is of any help
Iirc the aldehyde is attacked before the epoxide right?
Greater δ+ there?
yes aldehyde first then epoxide
excess MeMgBr so all possible sites will be attacked
also it specifies triols
Consider strain though
Oh wait I'm tweaking
Naah how could you attack the aldehyde while epoxide being the more reactive moiety there
Epoxide ring opening happens even in just water with ph 7
It’s a freakin nucleophile out there in the reaction mixture
Could you please check the products once again and show their formation “step-by-step”
‘cause I don’t think it’s gonna happen this way
Yup, I'm dumb sorry. This is acid catalysed epoxide thing so occurs via carbocation formation. Hence, the configuration on 2nd carbon from left is indeed not fixed in the above diagram. (So the 2 corner aldehyde wale carbons and the 2nd carbon from the left are chiral and show R and S configuration)
Do wait for someone to confirm though.
open epoxide nd then attack aldehyde . are prods diff ?
Acid catalysed?
It can't be grignard won't survive with an acid
idk why i cant digest R and S
I didn't check tbh
h2o serves as acidic medium and h3o+ as basic for epoxide rxns
(from my observation)
If this reaction is being carried out in h20
It would be an acid base reaction
And methane would be released
No nucleophilic addition as we expect
How's h30+ basic btw?
As the media isn't specified, you shouldn't consider the grignard vaali rxn to be in aqueous media
You should consider hexane or THF kinda things as the media
The configuration will remain fixed as there's no acid or base in the media and it would go like an SN2 kinda mechanism (no H+ to take up the lone pairs of Oxygen)
Hydrolysis baad me Kiya hai as the original question said
Was this clear @hardcoreisdead ?
(I'm very confident at this point that there's some issue with the answer key but if someone brings in another perspective, please do)
Oh right....
Well then ig it should be 4.
i honestly dk its just my observation
How does H3O+ behave?
It provides an H+ right?
How can it be a base then?
conjugate base of h2o
ig
uhhh its getting so confusing
Yeah I guess in that sense
Don't be trust me this is very simple
1. we knew the rxn not the number of products
2. we dont know the rxn
We know the reaction
We definitely do
what is it
Epoxide ring opening
Followed by nucleophilic addition
And the number of products is 4
so the products i sent were correct?
Let me see once again...
Take a look at the picture I sent as well
i shared this
can u reshare
this?
Yeah this one
Ek second
I just noticed the right and the left things are the same
Lmao
Gives you your answer I suppose or should I explain?
Thia should summarise everything
Also the attack is acidic because grignard attacks first , then h2o , not because h2o is considered acidic ( it's basic acc to rxns in my book)
epoxide ring opening in basic medium is in sn2 fashion hence the carbon's stereochemistry is fixed there
here acidic medium is used so not fixed stereochem
also
first epoxide opens, then both the cho are oxidised ( ques specifies triols)
@Varun_Arora @SirLancelotDuLac pls verify
The attack can't be acidic here
@hardcoreisdead
Grignard reagents are acid sensitive
Agar acid daal diya to reaction hogi hi nahi ye
CH4 nikal jayega
😭
u r right
this ques sucks ahhhh
Question doesn't suck bhai ye vala thik hai
Answer galat hai
Sometimes one gotta believe common sense over jargon
Don't think of ways to make the given answer "correct"
Rather try to think of the correct answer and be sure of it
true true
So....
We are done?
I guess mark solved now
sir se confirm karke karta hu
Hmm sure
Btw
Good luck
You're doing good amount and quality of questions buddy
2026 me de rahe ho?
yepp
thanxx
Dropper ya 12th?
currently in 12th
Damn
Ngl you're way ahead
Ya start hi organic se kiya tha?
start hi organic se hua tha
test had alkyl halides and aryl halides , alc phenol ether
Hmm then alright
All the best
,rotate
@Varun_Arora
Damnnnnnnnnnnn
@hardcoreisdead
Bro this is something that never crossed my mind amidst all this
Thanks a lot for posting this here
genius big brain ques
anytime
marking it solved now
+solved @Varun_Arora
Post locked and archived successfully!
Archived by
<@741159941934415883> (741159941934415883)
Time
<t:1748490958:R>
Solved by
<@984016629119713290> (984016629119713290)