(b) (i) Phenol and benzoic acid can be distinguished by ferric chloride test.
Ferric chloride test:
Phenol reacts with neutral FeCl3 to form ferric phenoxide complex giving violet colouration.
6C6H5OH + FeCl3 → [Fe(OC6H5)6]3− + 3H+ + 3Cl−
Phenol trace-phenol complex (violet colour)
But benzoic acid reacts with neutral FeCl3 to give a buff-coloured precipitation of benzoate.
3C6H5OH + FeCl3 ⇌ (C6H5COO)3Fe + 3HCl
Benzoic acid Ferric benzoate (Buff coloured ppt)
(ii) Benzophenone (C6H5COC6H5) and acetophenone (C6H5COCH3) can be distinguished by iodoform test.
Acetophenone, being a methyl ketone on treatment with I2/NaOH undergoes iodoform reaction to give a yellow ppt. of iodoform. On the other hand, benzaldehyde does not give this test.
C6H5COCH3 + 3NaOI → C6H5COONa + CHI3 + 2NaOH
Acetophenone → Iodoform
C6H5COC6H5 + NaOI → No yellow ppt
(a) (i), (ii) and (iii) - Ref image