Fundamentals of Organic ChemistryChemistryAmines
Identify the major product formed in the following reaction:
Correct answer
2
Step-by-step solution
The given reactant is N,N -dimethylaniline, which is a tertiary aromatic amine. The reagent mixture of NaNO ₂ and HCl generates nitrous acid ( HNO ₂ ), which produces the nitrosonium ion ( NO ^+ ) as an electrophile. Tertiary aromatic amines undergo electrophilic aromatic substitution when treated with nitrous acid. The - N(CH ₃)₂ group is strongly ring-activating and directs the incoming electrophile to the ortho and para positions. Due to significant steric hindrance at the ortho position, the electrophile ( NO ^