JEE MainChemistryAmines
The major product formed in the following reaction sequence is: o -Toluidine (i) Ac ₂ O, pyridine (ii) Br ₂ , CH ₃ COOH (iii) H ₃ O ^+ , heat (iv) NaNO ₂ , HCl, 0^ C (v) H ₃ PO ₂ Product
Options
- A2-Bromotoluene
- B3-Bromotoluene
- C4-Bromo-2-methylphenol
- D4-Bromo-2-methylaniline
Correct answer
B. 3-Bromotoluene
Step-by-step solution
Step (i): Reaction of o -toluidine (2-methylaniline) with acetic anhydride ( Ac ₂ O ) in pyridine protects the amino group, forming N -(2-methylphenyl)acetamide. Step (ii): Bromination ( Br ₂/ CH ₃ COOH ) of the protected amine occurs predominantly at the para position with respect to the strongly activating - NHAc group due to steric hindrance at the ortho position. This yields 4-bromo-2-methylacetanilide. Step (iii): Acidic hydrolysis ( H ₃ O ^+ , heat) removes the acetyl protecting group, producing 4-bromo-2-met