Ether Cleavage using HBr

[Bromo_DragonFly]

Ok, Just a question rised in my mind after seeing a few videos on ether cleavages using Hbr or HI.

the products of the examples given in videos were often phenols, or basically the ether was symmetric. so they don't answer the question for examples like the attached picture.

 

Which of the following will be the results of this cleavage ?

A or B ? (or maybe a C where both products are halides.)

 

thanks for any guide .

[Altered State]

It would depend on what R is. In general, the nucleophile (in this case Br-) would attack the less hindered carbon of the two that are bond to the ether oxygen, so if R is not a -C(Ph)3 o something like that, your compound would get cleaved to product B.

 

Your suggesiton of both becoming bromides can be possible in case that more than one mole of HBr is used. The alcohol would just undergo a substitution due to acidic conditions.