A mixture of benzoic acid , aniline and phenol is dissolved in chloroform and the solution is treated with NaOH, HCl , and NaHCO3 . Show a separation chart , identify the composition of each phase and explain the chemistry of the separation process.

Answer 1

This site does not support diagrams; therefore, I can't draw a flow diagram/separation chart. Here is what you do; you will need to take this information and make your own chart.
1. Treat with HCl. That will dissolve the aniline and the aniline:HCl salt will dissolve in the water layer. I assume you can write the equation. Place the solution in a separatory funnel. The chloroform layer will contain the benzoic acid and phenol.
2. Add NaHCO3 to the CHCl3 layer. Benzoic acid is a strong enough acid it will form a salt with NaHCO3. The phenol will not react. Write an equation for the benzoic acid + NaHCO3. That salt will be soluble in water but the phenol will remain in the chloroform layer. Place in a sep funnel and separate the two layers.
3. Adding NaOH will form a salt with the phenol.
I hope this helps.