Sciencemadness Discussion Board

Phenylsodium>Phenol

=SkyNET= - 15-5-2006 at 07:48

How would I replace the Na with OH?

Sorry if this seems basic, but I can't find anything.

C6H5Na+H2O>NaOH+C6H6

Maybe peroxide?

[Edited on 15-5-2006 by =SkyNET=]

Maja - 15-5-2006 at 08:09

C6H6 is benzene, not phenol. I think it should work with HCl.

[Edited on 15-5-2006 by Maja]

12AX7 - 15-5-2006 at 08:14

I don't see it, HCl would just leave the Na with the Cl and H with the C6H5 part.

A load of OH radicals probably would do it, H2O2 for instance, but I get the feeling weird stuff like peroxides and other reactions like straight hydration would be preferred (unless you have nasty high test peroxide).

Tim

=SkyNET= - 15-5-2006 at 08:27

I figured peroxide might work.

I guess i should expect a vigorous reaction.

Quote:
C6H6 is benzene, not phenol. I think it should work with HCl.


I left off a sentence in my post explaining why i hydroxide wouldnt work. :p

[Edited on 15-5-2006 by =SkyNET=]

unionised - 15-5-2006 at 09:35

Phenyl sodium wil deprotonate H2O2 to give sodium peroxide and benzene. The reaction will probably be fast enough to start thermally decomposing the peroxide and I wouldn't like to be there when it happens.
I think that iodination then hydrolysis of the iodobenzene might work but I wouldn't like to bet on it and the hydrolysis isn't easy anyway.
C6H5Na +I2 --> C6H5I + NaI

C6H5I + H2O --> C6H5 OH +HI

Nicodem - 15-5-2006 at 12:00

I would assume phenyl sodium would be enough reactive to get oxidized by oxygen to sodium phenolate. However bubbling oxygen trough a solution of phenyl sodium would be extremely stupid with regards of safety. Especially if the solvent would be combustible, it would be a bomb just waiting to explode (all alkyl metals are highly pyrophoric and I never heard of their "controlled combustion"). I can't remember any noncombustible solvent that would be able to solvate PhNa so you better forget such an experiment.

Why do you want to perform such a useless transformation anyway?

[Edited on 15-5-2006 by Nicodem]

=SkyNET= - 15-5-2006 at 19:01

I agree with the safety mentions, but I have a certain plan for it.

How about chlorine?

C6H5Na+Cl2>C6H5Cl+NaCl

Then Cl>OH?

chemoleo - 15-5-2006 at 19:30

Sorry you realise that phenylsodium isn't exactly an easy to come by compound? Most amateur chemists would sell their mother for it! :o:D

You do realise there are plenty ways for making phenol with over the counter compounds??

leu - 15-5-2006 at 20:18

Clearly the originator of this thread has little knowledge of the properties of phenylsodium, or alkali metals as far as that goes :( There is no substitute for diligent study habits and the proper equipment when it comes to compounds as dangerous as phenylsodium, please listen to Nicodem unless you have a death wish :P

=SkyNET= - 16-5-2006 at 19:16

I planned on only using milligram quantities of course. Anyone who has worked with sodium knows how hazardous it is. :O

turd - 17-5-2006 at 09:34

Quote:
Originally posted by =SkyNET=
I planned on only using milligram quantities of course. Anyone who has worked with sodium knows how hazardous it is. :O

Sodium is completely harmless as long as you don't throw it in a bucket 'o water.
The problem with PhNa is the Ph-, not the Na+. ;)