Answers are given in the end-

1. How will you distinguish butanol, butan-2-ol and 2-Methylbutan-2-ol

2. How will you distinguish aniline and phenol?

3.How will you distinguish phenol and ethanol?

4.How will you distinguish ethanamine and N-Methyl methanine.

5.How will you distinguish Propanamine and N,N-Dimethylethanamine.

6.How will you distinguish Propanamine, N-Methyethanamine and N,N-Dimethylmethanamine.

7. How will you distinguish Ethanol and Ethanoic acid.

8.How will you distinguish Methanal and Ethanal?

9.How will you distinguish Propanal and Propanol.

10.How will you distinguish Propanol and Ethanol?

11.How will you distinguish Choloromethane and Chlorobenzene.

Answer-
1.When Licas reagent (ZnCl2 + HCl ) is added than turbidity appears immediately in Methylbutan-2-ol ( tertiary alcohol), turbidity appears after 5 minutes in butan-2-ol ( Secondary alcohol) and no turbidity appears in butanol ( Primary alcohol).

2.Phenol gives violet colour with neutral FeCl3 while aniline does not.

3.Ethanol gives red colour with ceric ammonium nitrate while phenol does not.

4.Ethanamine reacts with benzenesulphonyl chloride( Hinesburg’s Reagent) which is soluble in dilute solution of NaOH, whereas N-Methyl methanine reacts but insoluble in dilute solution of NaOH.

5.Propanamine reacts with benzenesulphonyl chloride ( Hinesburg’s Reagent) which is soluble in dilute solution of NaOH, whereas N,N-Dimethylethanamine does not react.

6.Propanamine reacts with benzenesulphonyl chloride ( Hinesburg’s Reagent) which is soluble in dilute solution of NaOH whereas N-Methyl ethanine reacts but insoluble in dilute solution of NaOH whereas N,N-Dimethylethanamine does not react.

7.Ethanol gives red colour with ceric ammonium nitrate while Ethanoic acid does not.
Or Ethanol gives frutty smell of esters with ethanoic acid and few drops of conc. H2SO4 whereas ethanoic acid does not. (Note- This is ester test)

8.Ethanal gives yellow ppt with a mixture of NaOH and I₂ while methanol does not ( Iodoform,s Test)

9.Propanal gives silver mirror or black ppt with Tollen,s reagent( AgNO3 + NH4OH) while Propanol does not.
Or Propanal gives red ppt with mixture of Fehling,s solution A ( solution of CuSO4) and B ( solution of sodium potassium tartarate and NaOH) while Propanol does not.
( Note- Aldehydes gives Tollens test and Fehling,s solution test while ketones does not.)

10.Ethanol gives yellow ppt with a mixture of NaOH and I₂ while propanol does not (Note-This is Iodoform,s Test given by compounds having three alpha hydrogen to carbonyl group or three beta hydrogen to alcoholic group)

11.Choloromethane gives white precipitate with AgNO3 but Chlorobenzene does not.