don't understand destroyer orgo 171

[Kneecoal]

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so we have benzoic acid, toluene, phenol, and... i can't think of what to call benzene with an NH2 group on it at the moment

If NaHCO3 was added, which would be in aqueous layer?

a) Sodium benzoate
b) toluene
c) sodium bicarbonate
d) sodium phenoxide
e) aniline

what happens here? (the answer is A)

 

[joonkimdds]

I am also studying this at the moment.
But if you read #170, you know that you use NaHCO3 to extract an acid and that's what we did in #171. We used NaHCO3 to make it react with carboxylic acid of the choices we have. I am guessing that whatever reacted will be in an aqueous solution??

 

[Kneecoal]

innnnnnteresting. thanks for pointing that out!

 

[BTtheman777]

HCO3- is a weak base. It can be used to deprotonate the acidic proton from benzoic acid. However it is not a strong enough base to displace the proton from phenol. Aniline and toluene would remain unreactive. Thus when you add the bicarbonate anion, it will displace the proton from benzoic acid. Thus the sodium benzoate salt will transfer into the aqueous layer since it is ionic leading to your extraction.