Which of the following reactions is not correctly reported?

Options

A. `PhCH(OH)CH_(3)underset(H_(2)//Pd)overset(HClO_(4))rarrPhCH_(2)CH_(3)`
B. `PhCH_(2)underset(H_(2)//Pd)overset(HClO_(4))rarrphCH_(3)`
C. `Ph_(2)C(OH)CH_(2)CH_(2)OHoverset(HClO_(4))underset(H_(2)//Pd)rarrPH_(2)CHCH_(2)CH_(3)`
D. `PhCOCH_(2)CH_(3)overset(HClO_(4))underset(H_(2)//Pd)rarrPhCH_(2)CH_(2)CH_(3)`

Answer

C

Explanation

The process whereby `H_(2)` breaks sigma bonds is called hydrogenolysis. It is carried out by treating the alcohol with `H_(2)//Pd` containing some `HClO_(4)`.
Hydrogenolysis product of `Ph_(2)C(OH)CH_(2)CH_(2)OH` is `Ph_(2)CHCH_(2)CH_(2)OH` because the nonbenzylic `OH` is not affeted.
In the fourth case, the ketone is first reduced to the alcohol with this reagent. note that in the fifth case, the ring `OH` is not reduced.