Under the optimum pH for each, benzenediazonium chloride couples with which of the following?

Abenzene
Bphenol (pH 9-10)
Cnitrobenzene
DN,N-dimethylaniline (pH 4-5)

Answer: B, D

The diazonium ion is a weak electrophile and couples only with strongly activated rings such as phenoxide and aromatic amines. Benzene is not activated and nitrobenzene is deactivated by the nitro group, so neither couples.

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