Question
An organic compound A has molecular formula C8H12 and is optically active It reacts with H2/Pt to give B(C8H18) which is optically inactive Careful hydrogenation of A with Pd/BaSO4 gives C(C8H14) which is still optically active Compound A reacts with Na in liquid ammonia to give Diastereomer of C, but it is optically inactive Deduce structures of A to D.