a) Carboxylic acids are acidic enough to dissolve in both 10% NaOH and NaHCO3. Phenols, ArOH, are weak acids and most phenols will not dissolve in 10% NaHCO3. How would you separate a mixture of a carboxylic acid (RCOOH), an amine (RNH2), a phenol (ArOH) and a hydrocarbon (RH) using chemically active extraction? Draw a flow chart to illustrate your separation. please let me know if flow chart cannot be created here
b) A mixture of an amine, RNH2, and other items in CH2Cl2 was extracted with 10% HCl. The aqueous layer was discarded. The organic layer contained no amine. What went wrong?