Question

An optically active compound A with molecular formula C8H14 undergoes catalytic hydrogenation to give an optically inactive product. Which of the following structures for A is (are) consistent with all the data?

Answer 1

Any compound that possesses a plane of symmetry in any conformation will be achiral. Achiral molecules are optically inactive. (a) The reactant and the product formed on catalytic dehydrogenation of the reactant are as follows: cat. Њ Reactant Product Both the reactant and the product are optically inactive due to the presence of plane of symmetry

, plane of symmetry plane of symmetry- .. symmetry plane of Optically inactive Optically inactive (b) The reactantand the productformed on catalytic dehydrogenation of the reactant are as follows:

cat. Њ Reactant Product The reactant is optically active due to the absence of plane of symmetrywhile the product possesses the plane and is optically inactive. plane of symmetry Optically active Optically inactive

(c) The reactantand the product formed on catalytic dehydrogenation of the reactant are as follows: cat. H Reactant Product The reactant is optically active due to the absence of plane of symmetrywhile the product possesses the plane and is optically inactive.

plane of symmetry Optically active Optically inactive (d) The reactant and the product formed on catalytic dehydrogenation of the reactant are as follows: cat. H2 Reactant Product

Both the reactant and the product are optically active due to the absence of plane of symmetry Optically active Optically active e) The reactant and the productformed on catalytic dehydrogenation of the reactant are as follows: cat. H2 Reactant Product Both thereactant and the product are optically inactive due to the presence of plane of symmetry

ープ Optically inactive Optically inactive

Therefore, the structures of compound A that are consistent with the data are, Option (b) Option (c)