One Mole of an Optically Active Compound,X,with the Molecular Formula

Multiple Choice

One mole of an optically active compound,X,with the molecular formula C₆H₈ reacts with three moles of hydrogen in the presence of a catalyst to yield an optically inactive product that cannot be resolved.X also exhibits IR absorption at approximately 3300 cm^-1.Which is a possible structure for X?

A) (E) -4-hexen-1-yne
B) (Z) -4-hexen-1-yne
C) (E) -2-hexen-4-yne
D) 2-methyl-1-penten-3-yne
E) 3-methyl-1-penten-4-yne