A mixture of benzoic acid, phenol and methylbenzene in ether is shaken with aqueous NaHCO3. (pKa values: benzoic acid 4.20, phenol 10.0, carbonic acid about 6.4.) The component that goes into the aqueous layer as its sodium salt is

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A mixture of benzoic acid, phenol and methylbenzene in ether is shaken with aqueous $NaHCO X_{3}$ . (pKa values: benzoic acid 4.20, phenol 10.0, carbonic acid about 6.4.) The component that goes into the aqueous layer as its sodium salt is

An acid reacts with

HCO X_{3} X^{-}

appreciably only if its pKa is clearly lower than that of carbonic acid. Benzoic acid (4.20) does, with evolution of

CO X_{2}

; phenol (10.0) does not, and methylbenzene is neutral.