Which of the following does NOT undergo azo coupling with benzenediazonium chloride under mild conditions?

Aaniline (pH 4-5)
Bphenol (alkaline medium)
Ctoluene
DN,N-dimethylaniline (pH 4-5)

Answer: C

The diazonium ion is a weak electrophile that attacks only strongly activated rings (OH, O-, NH2, NR2). Toluene, activated only by a methyl group, does not couple.

Practice Amines and Aromatic Nitrogen Compounds More on Coupling reactions and azo dyes

Previous questionNext question

More questions on Coupling reactions and azo dyes

Azo dyes are characterised by the presence of the group NEET level
Coupling of benzenediazonium chloride with phenol is carried out in mildly alkaline medium rather than in neutral or acidic medium because JEE Main level
Benzenediazonium chloride is added to N,N-dimethylaniline in weakly acidic medium (pH 4-5). The main product is JEE Main level
Benzenediazonium chloride is added to an alkaline solution of 2-naphthol. The red-orange dye formed is JEE Main level
Methyl orange is prepared by coupling the diazonium salt of one compound with a second compound. These two compounds are JEE Main level
Benzenediazonium chloride is coupled in mildly alkaline medium with 4-methylphenol (p-cresol). The product is JEE Main level