Fundamentals of Organic ChemistryChemistryAmines
Identify the major product formed in the following reaction.
Correct answer
2
Step-by-step solution
The given reactant, N-methylaniline ( Ph - NH - CH ₃ ), is a secondary aromatic amine. The reagent mixture of NaNO ₂ and HCl generates nitrous acid ( HNO ₂ ), which further produces the nitrosonium ion ( NO ^+ ) as an electrophile. NaNO ₂ + HCl HNO ₂ + NaCl HNO ₂ + H ^+ H ₂ O ^+- NO H ₂ O + NO ^+ Secondary amines react with the nitrosonium ion to undergo N-nitrosation, forming N-nitrosamines as yellow oily liquids. The lone pair on the nitrogen atom of the secondary amine attacks the NO ^+ ion, followed by the loss