Would it be possible to use HCL instead of a hypochlorite to oxidise acetone into CHCl3?
(didn't seem to fit into the Garage experiments column)thunderfvck - 28-3-2004 at 10:49
I don't think so.
Me thinks that using HCl will just protonate the carbonyl and will react with water to give you some acetals, perhaps! Cl- is a poor nucleophile and
so it won't attack.
...but maybe I'm wrong!...BromicAcid - 28-3-2004 at 10:56
No, it won't make chloroform.
However I've been in your boat, I went down a path involving trying to make chloroform from acetone and HCl. Eventually I realized that there
was no reaction that was evident so I figured that it might help if I oxidized the HCl, so I mixed equal volumes of HCl with H2O2 30% and finally an
equal volume of acetone, I got a reaction but no chloroform . Just goes to show
you a little knowledge can be much more dangerous then none.t_Pyro - 28-3-2004 at 11:03
The hypochlorite is required for the replacement of the 3 H's on the terminal carbon by chlorine. HCl has chloride ions, which would be useless
for the replacement of the H atoms. Cl<sup>-</sup> is a moderate nucleophile, but it can't replace H<sup>-</sup> since
the latter is a very strong base.
Some alternatives:
I<sub>2</sub> + NaOH to make iodoform
Cl<sub>2</sub> + NaOH to make HOCl in situ, and chloroform.Quantum - 28-3-2004 at 13:25
Quote:
I got a reaction but no chloroform . Just goes to show you a little knowledge can be much more dangerous then none.
LMAO!
From the frying pan into the fire!unionised - 29-3-2004 at 14:52
Acetone and HCl will give you a mixture of compounds, Diacetone alcohol and mesityl oxide will be among them (possibly mesitylene too, if you leave it
long enough).
The haloform reaction only works under alkaline conditions.xSPHYNXx - 17-4-2004 at 03:34
doesn't HCl and acetone give phorone? or is that only under certain conditions?The_Davster - 17-4-2004 at 11:25
. Just goes to show
you a little knowledge can be much more dangerous then none.