The structure of the compound that gives a tribromo derivative on treatment with bromine water is
(A)(see structure)✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
Bromine water brominates an activated aromatic ring, and a phenol directs the incoming bromine to the positions ortho and para to its −OH group. A tribromo product appears when exactly three such positions are open. The structure that offers three free ortho and para sites around the hydroxyl, and so yields a 2,4,6-tribromo derivative on treatment with bromine water, is the phenol drawn with those positions available.
JEE Main · 2006 · 30 Apr 2006 · Offline · Single correct option