Explain why ArOR ethers are cleaved to give RI and rather than ArI and ROH.

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Solution

$S_{N} 2$ attack on a carbon of a benzene ring does not occur nor does the high energy $C_{6} H_{5}^{+}$ form by an $S_{N} 1$ reaction. Hence $A r I$ cannot be a product even in an excess of conc. $H I$ .

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