JEE Main Chemistry question

An aromatic ether is *not* cleaved by HI even at 525 K. This compound is

(A)C₆H₅OCH₃ (anisole)
(B)C₆H₅OC₆H₅ (diphenyl ether)Correct
(C)C₆H₅OC₂H₅ (phenetole)
(D)CH₃OC₂H₅ (methyl ethyl ether)

Answer: (B)

Solution

Diphenyl ether has an aryl group on *both* sides of the oxygen, so there is no alkyl carbon available for the usual Sɴ2 attack of iodide that cleaves alkyl aryl ethers (such as anisole or phenetole, which *are* cleaved by HI to give phenol +

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Question ID VK-140155