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  4. When phenol is treated with D2SO4/D2O, some of the hydrogens get exchanged. The final product in this exchange reaction is

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Q. When phenol is treated with $D_2SO_4/D_2O$, some of the hydrogens get exchanged. The final product in this exchange reaction is

WBJEEWBJEE 2014Alcohols Phenols and Ethers

Solution:

In acidic medium, phenol exists in following resonating structures.
image
Since, $o / p$ positions are electron rich sites, so electrophile will attack on these site, i.e., hydrogen of these sites get exchanged by $D$ (deuterium). Hence, the final product of the
image