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Choose the correct option · Q6

Q.Anisole on heating with concerntrated HI gives
A. Iodobenzene
B. Phenol + Methanol
C. Phenol + Iodomethane
D. Iodobenzene + methanol

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Step 1. Recall the cleavage rule for aryl alkyl ethers (section 11.5.3). An aryl-oxygen bond is shorter and stronger than an alkyl-oxygen bond because of partial double-bond character from conjugation with the aromatic ring's pi system. When an aryl alkyl ether reacts with hot concentrated HI, cleavage therefore always occurs at the weaker oxygen-ALKYL bond, never at the oxygen-aryl bond.

Step 2. Apply to anisole. Anisole is C6H5-O-CH3 (methyl phenyl ether). Cleaving its O-CH3 bond (not its ring-O bond) with hot HI gives the aryl fragment as phenol (C6H5-OH, since the ring-oxygen bond survives intact) and the alkyl fragment as methyl iodide (CH3-I, the iodide ion having displaced the oxygen at the methyl carbon by SN2). …

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