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Can someone help me with OChem? I need to propose a mechanism

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Thread replies: 10
Thread images: 3

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.
>>
>>8955400
Brainlet
It's sn2


Although I can see why you would get that wrong
t. Biochem PhD Candidate
>>
File: 1.png (28KB, 2093x985px) Image search: [Google]
1.png
28KB, 2093x985px
>>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
>>
>>8955485

>sn2
>2 stereoisomers

oh you
>>
>>8955841
>>8955833
[math]shut^{the}*fuck^{up} = niggers[/math]
>>
>>8955485
>Biochemists in charge of knowing shit about OChem.
>>
>>8955833
Thanks a lot anon
>>
>>8955833
How does that first mechanism make sense? The carbocation should be at the tertiary centre after rearrangement.
>>
File: 1494968342693.png (163KB, 515x800px) Image search: [Google]
1494968342693.png
163KB, 515x800px
>>8955833
>>8955993
oh fuck I'm retarded, nevermind
>>
>>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.
Thread posts: 10
Thread images: 3


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