87.7k views
4 votes
write a mechanism for the formation of an azo dye from p-nitrobenzenediazonium hydrogen sulfate and 8-anilino-1-naphthalenesulfonic acid?

1 Answer

4 votes

Answer:

See explanation

Step-by-step explanation:

The formation of an azo dye from p-nitrobenzenediazonium hydrogen sulfate and 8-anilino-1-naphthalenesulfonic acid occurs through a diazo coupling reaction. The mechanism is as follows:

Step 1: Formation of the diazonium salt

p-nitroaniline is first diazotized using nitrous acid to form p-nitrobenzenediazonium ion (ArN2+).

ArNH2 + HNO2 + H2SO4 → ArN2+ + 2H2O + HSO4-

Step 2: Formation of the coupling partner

8-anilino-1-naphthalenesulfonic acid acts as the coupling partner. It is deprotonated by a base such as NaOH to form the anilinonaphthalene sulfonate anion (Ar'SO3-).

Ar'SO3H + NaOH → Ar'SO3- + H2O + Na+

Step 3: Coupling of the diazonium ion and coupling partner

The diazonium ion attacks the coupling partner, and a nitrogen-nitrogen (N-N) double bond is formed to produce the azo dye.

ArN2+ + Ar'SO3- → ArN=N-Ar'SO3- + H+

The azo dye that is formed is typically orange or red in color, depending on the specific coupling partners used.

User Hamza Waleed
by
7.7k points