[rleung]

Hi,

I have a problem where I need to separate a binary mixture which contains phenol and napthalene.  I am am entirely sure how to do this.  For phenol, I can only think of adding a hydrohalic acid to it, but that will yield a reaction like Ph-OH + HCl ---> Ph-Cl + H2O.  I have not had mechanisms formally yet since I just started Orgo 1 (meaning I have not had any mechanisms formally yet), but I read parts of an Orgo book this summer and that is how I know that that reaction will take place.  

Thanks so much.

Ryan

[Borek]

Hints to both your questions: aniline is a base, phenol is an acid.

http://www.chembuddy.com/?left=pH-calculation&right=bronsted-lowry-theory

[rleung]

Hmmm, I am so sorry or being so stupid, but I still am not sure what to do.  Would napthalene form an ether bond with phenol?  

[Borek]

You are overcomplicating. This question has nothing to do with organic chemistry and is quite similar to the aniline one.

[rleung]

Hmmm...I think I figured it out.  Would I put it in a solution of NaOH so that Ph-OH becomes Ph-O(-) which would be soluble in water, while napthalene would be soluble in any neutral organic solvent such as CH2Cl2 or diethyl ether?

Thanks.

Ryan

[Yggdrasil]

Yup.  Generally separations are done using the physical properties of a substane (acid/base character, size, polarity, sterics) and they generally do not involve using chemical reactions (other than acid/base reactions) to change the substances being separated.