1. KOC(CH3)3 is a base and CHCl3 becomes :CCl in its presence(carbene). Carbene is an electrophile.
2. H2/Pd gives syn addition with alkene. i.e., both the hydrogen atoms add from the same side of the double bond (the side which is sterically less hindered is preferred)
You should be able to proceed with these hints, i guess..