ether cleavage, sn1 or sn2?

[JP2740]

As in a diethyl ether + HBr

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[wanderer]

It depends on the intermediates as well as the starting compounds. If there is OEt2 and it gets cleaved via Sn1, there will be a primary carbocation, which is very unstable. However something like di-isopropyl ether can undergo Sn1 so there would be a competition between Sn1 and Sn2, and it would depend on things like solvent, temperature, and probably some other factors.

 

[TFS]

it depends. you have to look at the reaction conditions.

 

[sizillyd]

Pretty sure this would be cleavage. The lone pairs on the O would attack the hydrogen on the HBr, cleaving HBr. Br- would then attack the positively charged compound that is left after diethyl ether breaks.

 

[Cool Beans]

If the Oxygen is leaving from a tertiary or secondary carbon than ether cleavage proceeds through an SN1 mechanism.
If the Oxygen is leaving from a primary or methyl carbon, then ether cleavage proceeds through an SN2 mechanism.