The diazonium salt shown couples with N,N-dimethylaniline at pH about 4-5. Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The salt shown is 4-nitrobenzenediazonium chloride; the nitro group makes it a more electrophilic diazonium ion. Coupling with a tertiary arylamine occurs in weakly acidic medium, para to the NMe2 group (no N-H, so no N-coupling), giving 4-dimethylamino-4'-nitroazobenzene.

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