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When 4-(methoxymethyl)anisole is heated with excess concentrated HI, the major aromatic product formed is:

Options

  1. A1-Iodo-4-(iodomethyl)benzene
  2. B4-(Iodomethyl)phenol
  3. C1-(Iodomethyl)-4-methoxybenzene
  4. D4-(Hydroxymethyl)phenol

Correct answer

B. 4-(Iodomethyl)phenol

Step-by-step solution

The given molecule, 4-(methoxymethyl)anisole, contains two different ether linkages: an aryl alkyl ether ( -O-CH₃ attached directly to the benzene ring) and a benzyl alkyl ether ( -CH₂-O-CH₃ ). When heated with excess concentrated HI: 1. For the aryl alkyl ether, the Ar-O bond has partial double bond character due to resonance and is stronger than the O-CH₃ bond. Thus, cleavage occurs at the O-CH₃ bond, yielding a phenol ( -OH ) and methyl iodide ( CH₃I ). 2. For the benzyl alkyl ether, the Ar-CH₂-O bond cleaves re

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