mechanism needed

1....CH₃COCH(CH₃)₂
2.NOT GIVEN .ONLY HINT GIVEN

1) Pentan-2-one? One keto group is reduced.
2) Reduction is not successful. Substrate is not stable to strong acidic medium(medium reacts with -OH group). Carboxylic acids are not reduced in Clemmenson reduction, but their derivatives are.

If I give you an example mech of Clemmenson reduction will it be enough?
Check this out : http://www.organic-chemistry.org/namedreactions/clemmensen-reduction.shtm

why both cannot be reduced in (1)
(2) is not acid.........hint given for (2) is through hydrogenenolysis of OH group or olefins

NO

Then both groups could be reduced....if it specified one mole then only one group. I guess answer will be pentane then.