Fundamentals of Organic ChemistryChemistryAmines
Which of the following amines undergoes electrophilic aromatic substitution when treated with nitrous acid at 0^ C ?
Options
- ANone of these
- BC ₆ H ₅ NH ₂
- CC ₆ H ₅ N ( CH ₃)₂
- DC ₆ H ₅ NHCH ₃
Correct answer
C. C ₆ H ₅ N ( CH ₃)₂
Step-by-step solution
Primary aromatic amines react with nitrous acid at 0^ C to form diazonium salts. Secondary aromatic amines react with nitrous acid to form N-nitrosoamines, which separate as a yellow oil. Tertiary aromatic amines, such as C ₆ H ₅ N ( CH ₃)₂ , have no hydrogen atoms on the nitrogen atom. The highly activated benzene ring undergoes electrophilic aromatic substitution with the nitrosonium ion ( NO ⁺ ) at the para position to form p-nitroso-N,N-dimethylaniline. Answer: C ₆ H ₅ N ( CH ₃)₂