Question

You are given a vial containing a mixture of the following compounds

1-naphthol

Benzoic acid

Butyl acetate

Indole

Assume the compounds are soluble in (diethyl)ether and have limited (slight) water solubility.

Plan the separation of the compounds by extraction. You have a separatory funnel, your lab drawer, shared equipment, and the following reagents to use

Ether

5% NaOH

10% NaHCO3

5% HCl

12M HCl

6M NaOH

Na2SO4(s)

1.Describe the plan in words. Outline or describe the extraction(s) needed to separate the compounds. Bullet points are okay.

2.Diagram the plan in pictures. Create a complete flow chart for your extraction(s). It may be hand drawn.

3.Clearly state any limitations which would prevent the complete separation and recovery of the compounds.

EDIT- After the first step (adding ether to the vial of 1-naphthol, Benzoic acid, Butyl acetate, Indole), do you add an Acid (HCl) OR Base (NaOH) to separate the organic from the aqueous layers?

Answer 1

LIMITATION :- limitation of this process will be that while adding acid or base one form will not be completely dissociated or other forms will be dissociated ( for example on adding base some of benzoic acid may not dissociate so will remain soluble in ether and cause impurity for rest solution)

2) addition of acid and base may cause in breaking of easter bond in butyl acetate. so this may also lead to impurity.