MolSynapsequestion bank
MolSynapse / Question bank / Structural Identification and Practical Organic Chemistry / Purification: distillation, crystallisation, chromatography
JEE Advanced levelSingle correct optionDifficulty 3 of 3si101

An ether solution contains benzoic acid, phenol, aniline and naphthalene. It is extracted successively with (1) dilute aqueous HCl, (2) aqueous , (3) aqueous NaOH. The species present in the three aqueous extracts and in the final ether layer are respectively

  1. Aanilinium chloride; sodium benzoate; sodium phenoxide; naphthalene
  2. Bsodium phenoxide; sodium benzoate; anilinium chloride; naphthalene
  3. Canilinium chloride; sodium phenoxide; sodium benzoate; naphthalene
  4. Danilinium chloride; sodium benzoate; naphthalene; sodium phenoxide

Answer: A

Dilute HCl protonates the basic aniline to the water-soluble anilinium chloride. removes only the stronger acid, benzoic acid, as sodium benzoate; phenol is too weak an acid. NaOH then converts phenol into sodium phenoxide. Neutral naphthalene remains in ether.
Practice Structural Identification and Practical Organic Chemistry More on Purification: distillation, crystallisation, chromatography
Previous questionNext question

More questions on Purification: distillation, crystallisation, chromatography