Exams › JEE Advanced › Chemistry

Which of the following amines forms an N-nitrosoamine when treated with NaNO2 and HCl?

1. p-Methylaniline (p-toluidine)
2. Aniline
3. A secondary aliphatic cyclic amine (e.g., pyrrolidine)
4. N-methylaniline (C6H5-NH-CH3)

Correct answer: N-methylaniline (C6H5-NH-CH3)

Solution

When amines react with NaNO2 + HCl (which generates HNO2 in situ): - Primary aromatic amines (aniline, p-toluidine): form diazonium salts (ArN2^+Cl⁻) at 0-5 deg C. - Primary aliphatic amines: form unstable diazonium ions that decompose. - Secondary amines (either aliphatic or aromatic-secondary like N-methylaniline): form N-nitrosamines (R2N-N=O). - Tertiary amines: do not react in the same way. Here, option (C) is a secondary aliphatic cyclic amine and option (D) is N-methylaniline (secondary amine). Both are secondary amines. However, among the options, N-methylaniline (C6H5-NH-CH3) is explicitly a secondary amine, making it the direct answer.

Related JEE Advanced Chemistry questions

• Which of the following transformations represents the correct reduction of an amide using LiAlH4?
• Among arylamines, alkylamines, and ammonia, the order of basic strength is:
• When C₆H₅NH₂ reacts with AlCl₃ and CH₃Cl, no reaction occurs. What can be inferred about the directing nature of the (-NH₂, AlCl₃) substituent?
• Diazomethane is capable of transferring a methyl group to certain functional groups. Compound IV contains an enolic —OH group, so it can undergo methylation by CH₂N₂. Which of the following is correct?
• In the reaction sequence: A --[SnCl2/HCl]--> B --[NaNO2/HCl, 0 deg C]--> C --[H2O/heat]--> C6H5OH. Identify compounds A, B, and C.
• Which of the following chemical tests can specifically identify a primary amino (-NH2) group in an organic compound?

⚔️ Practice JEE Advanced Chemistry free + battle 1v1 →