COMEDK2023Evening ShiftChemistryAminesActual
What would be the final product [ X ] formed when p-Toluidine undergoes the following series of reactions? aligned & P-Toluidine [ Pyridine ] CH ₂, CO ₂ O . [ P ] & [ P ] Br ₂ / CH ₃ COOH [ O ] & [ Q ] [ ] dilнG [ R ] & [R] [0^ C ] Nan ₂ / HCl [S] & [ S ] H ₂ PO ₂ [ X ] aligned
Correct answer
3
Step-by-step solution
The starting material is p-toluidine (4-methylaniline). Reaction with acetic anhydride in pyridine protects the amino group as an acetanilide derivative, forming p-methylacetanilide [P]. Bromination of p-methylacetanilide with Br₂/CH₃COOH occurs at the ortho position relative to the amino group (which is the position ortho to the -NHCOCH₃ group and meta to the -CH₃ group), yielding 2-bromo-4-methylacetanilide [Q]. Hydrolysis of the acetamido group in dilute acid with heating yields 2-bromo-4-methylaniline [R]. Diaz