Principle involved in the test:

Nitration: A process in which a nitro group (NO2) becomes chemically attached to a carbon, oxygen, or nitrogen atom in an organic compound. A hydrogen or halogen atom is often replaced by the nitro group.

Aromatic nitration: Typical nitration that uses nitric acid and sulfuric acid, in which this mixture produces the nitronium ion (NO2+), which is the active species in aromatic nitration. The sulfuric acid is not consumed and hence acts as a catalyst as well as an absorbent for water.

Type of Reaction:

Electrophilic aromatic substitution : is an organic reaction in which an atom, which is usually hydrogen, added to an aromatic system is replaced by an electrophile. In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile. Because electrophiles accept electrons, they are Lewis acids.

Ex.: Electrophilic aromatic substitution of benzene

Place 1.0 mL of conc. HNO3 in an Erlenmeyer flask. Immerse the vial in an evaporating dish containing water and gradually add 1.0 mL of conc.

H2SO4. Keep the vial steady by using a crucible tong. Cool the resulting
mixture to room temperature. This will serve as the nitrating mixture.

Place 5 drops of the following: cyclohexene, toluene in dry test tubes. Add 8 drops of the nitrating mixture. Shake the test tube to ensure complete mixing. Note the formation of a yellow oily layer or droplet. Dilute with 20 drops of distilled water.

If there is no apparent reaction observed within a minute, place the test tube in water bath for 10 minutes. Dilute with 20 drops of water. Note down the results.

Structure / Formula of Sample

Test Sample

Observation

Structure / Formula of Compound After Nitration

Cyclohexene

NR, oily like layer on top of the mixture, similar to the separation of oil & water. As the reaction occurs, the color goes from clear to yellow.

Toluene

Note: In both cases, the oily layer is probably just unreacted organic material separating from the water. Cyclohexene and toluene are both less dense than water, so will rise to the top in a solution of aqueous acid.

Sample Equation using a sample that gave a positive result: