JEE PYQ: Haloalkanes And Haloarenes Question 26
Question 26 - 2019 (11 Jan Shift 2)
Which of the following compounds will produce a precipitate with $\text{AgNO}_3$?
(1) Pyridyl bromide (Br on N-containing ring)
(2) Bromobenzene
(3) Bromocyclohexene
(4) Bromocyclohexane
Show Answer
Answer: (2)
Solution
Cycloheptatrienyl bromide (tropylium bromide) readily ionizes to form the aromatic tropylium cation ($6\pi e^-$), which precipitates AgBr with $\text{AgNO}_3$.