Nasalguad
Harmless
Posts: 7
Registered: 15-12-2013
Member Is Offline
Mood: nice
|
|
Nucleophilic substitution on an alky fluoride
Hi everyone, have a question that I just can't seem to wrap my head around. I recently came across an old canister of 1,1,1,2-Tetrafluoroethane, an
old refridgerant, and started thinking about what sorts of reactions it would undergo. I started thinking of possible products that would form from
passing a stream of Tetrafluoroethane gas through a sodium hydroxide solution. Would the reaction generate four molecules of NaF and a tetrally
substituted ethane molecule? or would the reaction cease once one or two hydroxyl groups are added due to steric effects from the hydroxide groups?
|
|
|
blogfast25
International Hazard
Posts: 10562
Registered: 3-2-2008
Location: Neverland
Member Is Offline
Mood: No Mood
|
|
https://en.wikipedia.org/wiki/Tetrafluoromethane#Reactions
Trust me, it's the same for 1,1,1,2-Tetrafluoroethane.
|
|
|
MeshPL
Hazard to Others
Posts: 329
Registered: 20-4-2015
Location: Universe
Member Is Offline
Mood: No Mood
|
|
It will not react with NaOH, but with Na it may actually produce some NaF. The only problem is, the fact that tetrafluoroethane is gaseous in room
temperature will reaction with Na would be exothermic and may require preheating. So all your reagent may escape. And in fact the reaction mixture may
explode  .
In fact Teflon, which is a highly substituted fluorocarbon makes a good flash powder with Mg, so tetrafluoromethane may as well  .
[Edited on 7-10-2015 by MeshPL]
|
|
|
blogfast25
International Hazard
Posts: 10562
Registered: 3-2-2008
Location: Neverland
Member Is Offline
Mood: No Mood
|
|
Quote: Originally posted by MeshPL  | It will not react with NaOH, but with Na it may actually produce some NaF. The only problem is, the fact that tetrafluoroethane is gaseous in room
temperature will reaction with Na would be exothermic and may require preheating. So all your reagent may escape. And in fact the reaction mixture may
explode .
In fact Teflon, which is a highly substituted fluorocarbon makes a good flash powder with Mg, so tetrafluoromethane may as well .
[Edited on 7-10-2015 by MeshPL] |
Halogenated carbons and alkali metals are a recipe for disaster.
|
|
|
gdflp
Super Moderator
Posts: 1320
Registered: 14-2-2014
Location: NY, USA
Member Is Offline
Mood: Staring at code
|
|
This can actually be used to make a really nice demonstration. If a small(3mm x 3mm x 3mm) piece of sodium is placed in a test tube and melted over a
flame, a few drops of an alkyl iodide can be added. This results is a sharp crackle, followed by tube filling with purple iodine vapor, the reaction
is actually quite beautiful. This is also one way of fusing the iodide into sodium iodide, so further tests can be performed and the organic compound
qualitatively determined.
|
|
|
MeshPL
Hazard to Others
Posts: 329
Registered: 20-4-2015
Location: Universe
Member Is Offline
Mood: No Mood
|
|
| Quote: |
Halogenated carbons and alkali metals are a recipe for disaster.
|
Everything depends on concentration and amount. I thought it was a recipe for Wurtz reaction, which is a really crappy C-C bond formation  .
But still don't mess with alkali metals + halocarbons.
|
|
|
Nasalguad
Harmless
Posts: 7
Registered: 15-12-2013
Member Is Offline
Mood: nice
|
|
Thanks everbody who responded that is all exactly what I was looking for and fantastic information. Well now that alcohol formation is out of the
question, anybody got any ideas on any non-explosive reactions that I could do with this stuff?
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
