Aldehydes, Ketones and Carboxylic Acids

Both phenol and benzoic acid are soluble in NaOH, so they cannot be separated
C6H5OH+NaOH → C6H5ONa+H2O
C6H5COOH+NaOH → C6H5COONa+H2O
Benzyl alcohol C6H5CH2OH is not soluble in NaOH and NaHCO3, while benzoic acid is soluble in both, so these can be separated. Both C6H5OH and C6H5CH2OH are insoluble in NaHCO3, so they cannot be separated. C6H5CH2COOH is soluble in NaOH and NaHCO3, whereas benzyl alcohol is not soluble in NaOH and NaHCO3. So, they can be separated.