stygian - 15-12-2005 at 21:23
If 1mol ether (say, diphenylmethyl dimethylaminoethyl ether) is cleaved with 1mol HBr or HI, would the products be both the alcohol and the halide
version of each fragment? Or is there some determining factor here?
[Edited on 16-12-2005 by stygian]
BromicAcid - 15-12-2005 at 22:01
I believe that there is a degree of specificity to the process under certain conditions although the specific markers denoting which side will obtain
the halide and which side the alcohol group have long since been forgotten. Note that an excess of HBr will lead to both products being alkyl
bromides, so less confusion.
Darkblade48 - 16-12-2005 at 00:03
Given any primary/secondary ether, the Sn2 pathway is the major pathway. You'd see initial protonation on the oxygen then attack of the iodine/bromine
at the least hindered carbon.
For a a tertiary/allylic/benzylic ether, the cleavage occurs via a carbocation intermediate
This is good practice for my organic chemistry exam in a few days 
Marvin - 16-12-2005 at 06:03
Hmm, will this cleave at all, or just form a salt?