Hi! I know that the basic rule is: use a weak basic solvent to extract an acid, and use a weak acid solvent to extract a base. That being said, to extract an amine (an base with a lone pair electron), we should use an acid, correct? And to extract a phenol (an electron-donating base), we should use an acid as well. My confusion came from Destroy gchem #150 b/c the answer key's different from my conclusion.
extraction technique
- Thread starter siba
- Start date
- Joined
- Feb 15, 2008
- Messages
- 3,809
- Reaction score
- 10
For a phenol, you have to use a base. Acid doesn't make sense. Ar-OH2 just doesn't make any sense...too unstable. Ar-O- looks better 🙂
- Joined
- Dec 20, 2007
- Messages
- 220
- Reaction score
- 0
I think what he was trying to get across it that phenols are extremely acidic due to its conjugate base being extremely weak and in full conjugation with the ring system. You would use a base to extract a phenol because you would deprotonate the H in the process making it a salt with whatever spectator ion was used in the base. This would take the phenol out of the organic layer and bring it into the aqueous layer which is the whole point.
This is the order of acidity in descending order from top to bottom and Left to right:
phosphoric acids
Diesters
carboxylic acid dr: acylhalides>anhydrides>thioesters>esters>amide>ether
Phenols>alcohols
Aldehydes
ketones
-
So phenols are quite acidic. I hope this helps.
phosphoric acids
Diesters
carboxylic acid dr: acylhalides>anhydrides>thioesters>esters>amide>ether
Phenols>alcohols
Aldehydes
ketones
-
So phenols are quite acidic. I hope this helps.
Last edited:
