Q: Why can I not separate 2-naphthol first?


In general, acidic organic compounds are extracted with an aqueous inorganic base such as NaOH. NaOH is a strong inorganic base and both benzoic acid (a carboxylic acid) and 2-naphthol are ionized to a salt in the presence of NaOH.

  • Benzoic Acid
  • C7H6O2
  • pKa: 4.18
  • 2-naphthol
  • C10H8O
  • pKa: 9.57

Reference: G. Marc Loudon, Organic Chemistry, 3rd ed., Benjamin/Cummings Publishing Co, Inc,

click here to go back and try again!