Which of the following compound will not undergo Azo coupling reaction with benzene diazonium chloride?

Nitrobenzene

The correct answer is 2. Nitrobenzene.

The correct answer is 2. Nitrobenzene.

Azo coupling reaction is a reaction between a diazonium salt and an electron-rich aromatic compound. Nitrobenzene is an electron-deficient aromatic compound due to the presence of the nitro group \((-NO_2)\). Therefore, nitrobenzene will not undergo azo coupling reaction with benzene diazonium chloride.

The other three compounds, aniline, phenol, and anisole, are all electron-rich aromatic compounds and will undergo azo coupling reaction with benzene diazonium chloride.

Here are the reactions: