medium · MCAT chem-phys
An organic chemist attempts to separate a mixture of a carboxylic acid and a phenol using extraction.
If the mixture is dissolved in an organic solvent and shaken with an aqueous solution of NaHCO_3 (a weak base), which species will move into the aqueous layer?
- Only the phenol, because its aromatic ring makes it more polar.
- Both the carboxylic acid and the phenol will move to the aqueous layer.
- Only the carboxylic acid, as it is acidic enough to be deprotonated by NaHCO_3.
- Neither compound will move, as both are primarily soluble in organic solvents.
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