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Author: Subject: Ether cleavage
stygian
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[*] posted on 15-12-2005 at 21:23
Ether cleavage


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]
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BromicAcid
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[*] posted on 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.



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Darkblade48
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[*] posted on 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 :)
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Marvin
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[*] posted on 16-12-2005 at 06:03


Hmm, will this cleave at all, or just form a salt?
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