Question

What is the functional group analysis of the compound nitro toulene? The compund only dissolves in H2SO4 and it tunr yellow. It is not soluble in HCl, water, or NaHCO3

No2

These are the instructions given to me:

Write chemical equations that account for the observed solubility behavior of the unknown in acids and bases. Hydrocarbons or alkyl halides with no chemical reason to dissolve in the acids and bases should not dissolve in them. A prose explanation is necessary.

Answer 1

Two tests for aromatic nitro compounds:

1. Reduction with Tin and HCl:

Reflux to a clear slution a mixture of 0.5 g of the substance with 5 mL of conc HCl, 2 mL of alcohol and 3 small pieces of granulated tin metal. Cool and decant the mixture from unchanged tin. This converts nitro into amino group.

To 2 mL of this solution, add 2 mL of water and cool to 5 ^oC in an ice bath. Add dropwise 1 m/l of 10% cold aqueous NaNO2 solution and stirr well.

Add 1 mL of this diazotized solution to 5 mL of an ice cold alkaline beta-naphthol solution. A red or orange dye indicates the presence of a nitro group.

2. Mulliken`s test:

This is the best method, without any anomaly, for detecting a nitro group.

Warm gently to dissolve 0.1 g of the compound with 1 mL of alcohol and 1 mL of water. Now, add 0.5 g of solid NH4Cl and pinch off zinc dust. Boil the mixture gently for 3 minutes and filter directly into 5 mL of Tollen`s reagent. A black precipitate indicates nitro group.