maniacscientist
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Acid strength
Hello,
I was wondering, if one had a HCl salt of an arylaminoalkane, and wanted halogenat it, would the salt (beside differnce in solubility etc.) behave
differently from the base in this reaction?
As if one wanted to brominate an acetate salt, it will yield the brominated ring along with the hydrobromide salt of the compound.
Would the same happen to the HCl?
I´m just trying to understand what the difference is, is it that HBr is so much stronger Pka than ACOH ?
maniac
[Edited on 27-12-2007 by maniacscientist]
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solo
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Perhaps relevant....but recently in trying to halogenate an amino alcohol I found that the HCl salt of the alcohol would halogenate easier than the
base ...reason, the HCl created some sort of steric hindrance and the halogenatio went smoothly....therefore deduction is that the HCl will cause
hindrance with your arylaminoalkane so the base should have an easier time haloganating.....it's how I see it.......solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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syntelman
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Bromination of the freebase will most likely lead to partly N-brominated end product. And whether you use the acetate or hydrochloric acid salt will
not make any difference, but you will end up with a mixture of different salts (with the strongest acids salt as predominant) which is easily solved
by an acid/base extraction.
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