regioselective13 - 6-4-2015 at 10:17
So I was looking at this thread about making potassium metal from the hydroxide
http://www.sciencemadness.org/talk/viewthread.php?tid=14970
and I was wondering if chlorobutanol would be an acceptable catalyst for the reaction. It's a non-aromatic tertiary alcohol so it looks good from a
first glance, but would the trio of chlorine atoms pulling electron density away have any effect on the efficacy?
[Edited on 6-4-2015 by regioselective13]
Metacelsus - 6-4-2015 at 12:39
Chloro groups react with alkali metals.
j_sum1 - 6-4-2015 at 16:01
The space filled molecular model really makes it clear that this is not quite the same thing. I am not claiming that the atomic radii are in the
correct proportion here, but it does illustrate just how much those chlorines dominate.
[edit]mumble mumble typo
[Edited on 7-4-2015 by j_sum1]
blogfast25 - 6-4-2015 at 17:10
Nothing chlorinated would work in that reaction. Any potassium formed (hypothetically) would react with the trichlorobutanol (whatever the isomer).
regioselective13 - 7-4-2015 at 13:04
Ahhh that makes sense now that I think about it, halogens are better leaving groups than alcohols, and if alkali metals can react with alcohols then
they will definitely react with a halogen.
blogfast25 - 7-4-2015 at 15:12
Good/bad leaving groups aside, mixing alkali metals and C-Cl bonds containing organics is a thoroughly bad idea. This post contains a link to
explosions caused by sodium and chloroform (the link to the *.pdf is old but still live):
http://www.sciencemadness.org/talk/viewthread.php?tid=5112#p...
nezza - 8-4-2015 at 10:44
As a rule of thumb heating organics containing chlorine with alkali metals is a BAD thing. They tend to decompose violently (explode). Any potassium
formed would certainly react with the chlorbutanol immediately.
[Edited on 8-4-2015 by nezza]