Which one of the following reactions is NOT possible?
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Answer
(3) [figure]
Solution
(A): –OCH3 is o/p-directing; Cl2/AlCl3 gives p-chloroanisole (major) ⇒ (A) is possible
(B): Dow's process — NaOH at 623 K, 300 atm, then H ⇒ phenol ⇒ (B) is possible
(C): C–O bond of phenol has partial double-bond character (resonance, sp2 carbon) ⇒ –OH is not replaced by Cl with HCl ⇒ (C) is NOT possible
(D): C6H5-O-CH3 + HBr C6H5OH + CH3Br ∵ Ar–O bond is strong, cleavage occurs at O–CH3 ⇒ (D) is possible
Answer: (3)