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Ice Inkberry
Ice Inkberry
01:58
Focusing on mains for now. My plans change every week. If I get bored of mains, I'll do advanced.
Jasmine
Jasmine
02:17
@IceInkberry I get inspired by the way you always enjoy your preparations.
 
5 hours later…
Abcd
Abcd
06:49
Ya
 
9 hours later…
Dante
Dante
16:17
@IceInkberry Hello, a small doubt.
user image
The following reaction was carried out in aprotic solvent
Doesn't the product suggest it must have proceeded through SN1?
I don't understand because I've read aprotic solvents support Sn2 mechanism
Dante
Dante
16:37
user image
Abcd
Abcd
What are the conditions? Post the exact question @Dante
What is the source?
Dante
Dante
My college material
Abcd
Abcd
What are the wordings?
What is the question?
Reagents? Temperature? Solvent?
Esha Manideep
Esha Manideep
@Dante It is indeed SN2 dante, but attack happens at the other carbon and double bond rearrangement happens.
sammy gerbil
sammy gerbil
← 5 messages moved from Problem Solving Strategies
Dante
Dante
16:39
Write the structure of the nucleophilic substitution products in each of the following in aprotic solvent
@Abcd Just solvent
Abcd
Abcd
@Dante Its an SN2' reaction. (S N two prime)
Dante
Dante
@EshaManideep Well, how did you make out's Sn2?
Esha Manideep
Esha Manideep
Let's both listen to abcd
Abcd
Abcd
are you being sarcastic?
Esha Manideep
Esha Manideep
No, I read it in March, but forgot
So, remind me please
Dante
Dante
16:42
@Abcd I don't remember reading about any kind of rearrangement in SN2 :/
Please explain
Abcd
Abcd
Attack happens at the double bonded carbon and the double bond shifts.
Esha Manideep
Esha Manideep
@Abcd reason is ?
Abcd
Abcd
@EshaManideep see the stability of the double bond in the product
Esha Manideep
Esha Manideep
So, it's basically thermodynamic control, is it ?
Dante
Dante
@Abcd Why there and not on the carbon having halogen?
Avnish Kabaj
Avnish Kabaj
16:45
Read 1,3 and 1,2 additions
Abcd
Abcd
@EshaManideep dont you see kinetics are also supporting it here
attack at less hindered
Avnish Kabaj
Avnish Kabaj
Wait no that's for carbonyl
Abcd
Abcd
hmm
Avnish Kabaj
Avnish Kabaj
Ngp
Esha Manideep
Esha Manideep
quora.com/…
Avnish Kabaj
Avnish Kabaj
16:46
That's it
Abcd
Abcd
@Dante Both thermodynamics and kinetics are supporting that
Esha Manideep
Esha Manideep
The first explanation is good
Abcd
Abcd
$SN2'$ is most common with RCu-BF3 combination
@Dante one minute
user image
10 mins ago, by Dante
@Abcd I don't remember reading about any kind of rearrangement in SN2 :/
7 mins ago, by Dante
@Abcd Why there and not on the carbon having halogen?
@Dante Why there? You answer: why not at the least hindered top carbon? Which is one of the main characteristic of SN2, nucleophile prefers least hindered electrophilic carbon
@Dante The aprotic solvent is even a supporter in this...because you know aprotic solvents favour SN2.
@Dante Also see the bottom of the above page pic.
I noted that from Clayden most probably.
That clearly shows that SN2' is strongly favoured at the least hindered carbon
Abcd
Abcd
17:07
@Dante And another thing: Thermodynamic support. More substituted double bond is more stable. After all this why wont the above product be major?

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