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AZO dye synthesis: Preform a miniscale diazotization of an aromatic amine to form a diazonium salt,...

AZO dye synthesis: Preform a miniscale diazotization of an aromatic amine to form a diazonium salt, then preform a miniscale coupling with a phenol to form a azo dye 2. The NaNO2 (sodium nitrite) serves an important purpose in this reaction. What is NaNO2 function?

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Answer #1

The diazotization reaction requires that you have an amine and nitrous acid

R-NH2 + HNO2 ------> (R-N2)^+1 + OTHER PRODUCTS

but the problem is... HNO2 is highly reactive and decomposes very easily

HNO2 ------> NO + H2O

so it can't be prepared and stored. So instead, it is prepared on the spot by reacting NaNO2 and HCl.

NaNO2 + HCl ----------> NaCl + HNO2

so that u can complete the reaction

Ar-NH2 + HNO2 -----> (Ar-N2)^+1 + other products

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