JEE PYQ: Aromatic Compounds Question 9
Question 9 - 2020 (05 Sep Shift 2)
The final major product of the following reaction is:
m-Methylaniline → (i) $\text{Ac}_2\text{O}$/Pyridine → (ii) $\text{Br}_2$, $\text{FeCl}_3$ → (iii) $\text{OH}^-/\Delta$
(1) 3-Methyl-2-bromoaniline
(2) 3-Methyl-4-bromoaniline
(3) 3-Methyl-6-bromoaniline
(4) 4-Bromo-3-methylaniline
Show Answer
Answer: (4)
Solution
Acetylation protects $\text{NH}_2$, bromination occurs para to $\text{NHCOCH}_3$, then hydrolysis restores $\text{NH}_2$.
BETA
