Benzoic acid-- Aqueous layer?

[ramin123]

Why is benzoic acid soluble in ether --- BUT NOT aqueous layer? – I though b/c of hydrogen bonds it will be soluble!?

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[ramin123]

Anyone?

 

[Dental4ever]

what's the complete question? i think you are right but if it's a mixture problem, it depends on what solution they use.

 

[ramin123]

It is a chem q on Top score #3. They had it mixed in with diethylether then added acid. They said that it protinates the aniline which transfers to the Aqueous layer?

I understand that part-- it is that i feel that the benzoic acid should have also been transferred into the aqueous layer.

What do you think?

 

[Dental4ever]

aniline is a base and will react with the acid which will form a aqueous layer. bezoic acid will not react with the acid. therefore will not form in aqueous layer

 

[ramin123]

But why doesn't benzoic acid mix with the aqueous layer? I understand that it will not react with the acid-- but even before it reacts with the acid shouldn't be able to mix in the aq layer b/c of h-bonding?

 

[doc toothache]

But why doesn't benzoic acid mix with the aqueous layer? I understand that it will not react with the acid-- but even before it reacts with the acid shouldn't be able to mix in the aq layer b/c of h-bonding?

Benzoic acid solubility in water is 2.9% at 20 C.

 

[futuredent22]

Even though it may be capable of forming a hydrogen bond and a dipole-dipole bond with water, that won't make up for the huge benzene ring that wouldn't be soluble at all in water. As doc toothach showed, benzoic acid isn't soluble at all in water.