An optically active compound A with molecular formula C 8 H 14 undergoes catalytic hydrogenation to give an optically inactive product. Which of the following can be the structure of A?

Question

TestHub · Accepted Answer

Ans. (D) B & C.

Sol. The product of hydrogenation must be an achiral dimethylcyclohexane while A itself must be chiral.

(B) trans-3,6-dimethylcyclohex-1-ene is chiral (no plane of symmetry); hydrogenation gives trans-1,4-dimethylcyclohexane, which is achiral.

(C) 1,4-dimethylcyclohex-1-ene is chiral (C₄ is a stereocentre); hydrogenation gives 1,4-dimethylcyclohexane, which is achiral.

(A) cis-3,6-dimethylcyclohex-1-ene itself has a plane of symmetry, so it is optically inactive and cannot be A.

Chemistry - STEREO ISOMERISM Question with Solution | TestHub

Options:

Doubts & Discussion