[bball34]

I'm stuck with a situation where I've already done a separation extraction  leaving me with naphthalene and benzoic acid in my organic layer of ethyl acetate and now I need to separate them. I feel that their properties  are too similar to effectively manipulate one of them to somehow separate them. If anyone has any suggestions I'd appreciate it!!! Thanks!!!

[taurean]

I'm stuck with a situation where I've already done a separation extraction  leaving me with naphthalene and benzoic acid in my organic layer of ethyl acetate and now I need to separate them. I feel that their properties  are too similar to effectively manipulate one of them to somehow separate them. If anyone has any suggestions I'd appreciate it!!! Thanks!!!

How do you think you can seperate? 

Hint: The seperation can be done utilizing the distinct chemical reactivity of benzoic acid.

[bball34]

would that be the same if it was possibly salicylic acid instead of benzoic acid? they are carboxylic acids so could I possibly make them into ions by adding  a base so they are soluble in water and the naphthalene stays in the organic layer? but I already used that technique  to seperate phenol from the mixture.... i have no idea... i'm so confused....

[taurean]

would that be the same if it was possibly salicylic acid instead of benzoic acid? they are carboxylic acids so could I possibly make them into ions by adding  a base so they are soluble in water and the naphthalene stays in the organic layer? but I already used that technique  to seperate phenol from the mixture.... i have no idea... i'm so confused....

Is it a three component mixture comprising of phenol, benzoic acid and napthalene?

[Yggdrasil]

Adding a base to deprotonate the benzoic acid and make it soluble in water would allow you to separate naphthalene and benzoic acid in EtOAc.  If you had a mixture of phenol, benzoic acid, and naphthalene, you could still separate the benzoic acid by taking advantage of the difference in pKa between benzoic acid and phenol.  For example, sodium bicarbonate is a strong enough base to deprotonate benzoic acid, but it will not deprotonate your phenol.

[mir]

For example, sodium bicarbonate is a strong enough base to deprotonate benzoic acid, but it will not deprotonate your phenol.

Be sure that is not an activated phenol with lots of methoxy groups attached to the ring. They have a pH lower than oridinary phenols.