JEE MainChemistryAmines
Consider the following reaction sequence: Aniline Acetic anhydride, Pyridine P conc. HNO ₃/ H ₂ SO ₄ Q (major product) Q H ₃ O ^+, R NaNO ₂/ HCl, 0-5^ C S -naphthol, NaOH T Identify the major product 'T'.
Options
- A1-(2-Nitrophenylazo)-2-naphthol
- B3-(4-Nitrophenylazo)-2-naphthol
- C4-(4-Nitrophenylazo)-1-naphthol
- D1-(4-Nitrophenylazo)-2-naphthol
Correct answer
D. 1-(4-Nitrophenylazo)-2-naphthol
Step-by-step solution
Step 1: Aniline reacts with acetic anhydride in the presence of pyridine to form acetanilide (P). This step protects the amino group and reduces its activating effect, preventing polysubstitution and oxidation during nitration. Step 2: Nitration of acetanilide with conc. HNO ₃ and conc. H ₂ SO ₄ yields p-nitroacetanilide (Q) as the major product due to steric hindrance at the ortho position. Step 3: Acidic hydrolysis of p-nitroacetanilide removes the acetyl group, yielding p-nitroaniline (R). Step 4: p-Nitroaniline