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/sci/ - Science & Math

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8955400 No.8955400 [Reply] [Original]

Can someone help me with OChem? I need to propose a mechanism for the reactions in pic related, i'm pretty sure it's Sn1 but i get lost at the carbocation rearrangement.

>> No.8955485

>>8955400
Brainlet
It's sn2


Although I can see why you would get that wrong
t. Biochem PhD Candidate

>> No.8955833
File: 28 KB, 2093x985, 1.png [View same] [iqdb] [saucenao] [google]
8955833

>>8955400
here you go OP, i colored the sigma bond involved in and adjacent to bond breaking to make it easier to understand

>>8955485
it's sn1

>> No.8955841

>>8955485

>sn2
>2 stereoisomers

oh you

>> No.8955861

>>8955841
>>8955833
[math]shut^{the}*fuck^{up} = niggers[/math]

>> No.8955906

>>8955485
>Biochemists in charge of knowing shit about OChem.

>> No.8955935

>>8955833
Thanks a lot anon

>> No.8955993

>>8955833
How does that first mechanism make sense? The carbocation should be at the tertiary centre after rearrangement.

>> No.8955994
File: 163 KB, 515x800, 1494968342693.png [View same] [iqdb] [saucenao] [google]
8955994

>>8955833
>>8955993
oh fuck I'm retarded, nevermind

>> No.8957470

>>8955485
>sn2
>rearrangement
>2 stereoisomers
turbo brainlet

>>8955993
>>8955994
its correct though
If you'd get a tertiary carbocation instead, you wouldn't get the product seen in the OP pic. It works because of ring strain. In reality, some of that 5-membered ring secondary carbocation would still undergo further rearrangement to give the tertiary carbocation (and then tertiary alcohol) though.