A chiral compound (X) with the molecular formula undergoes catalytic hydrogenation to yield a satura — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

Compound (X) is unsaturated ($C_5H_9Cl$) and hydrogenates to a saturated alkyl chloride ($C_5H_{11}Cl$). The saturated product must be resolvable into enantiomers, meaning it must retain a chiral center. A) 4-chloro-1-pentene hydrogenates to 2-chloropentane, which has a chiral center at C2. B) 3-chloro-1-pentene hydrogenates to 3-chloropentane, which has a plane of symmetry and is optically inactive (meso/achiral). C) 4-chloro-2-pentene hydrogenates to 2-chloropentane, which is chiral. D) 1-chloro-1-pentene hydrogenates to 1-chloropentane, which is a primary halide and achiral. Thus, A and C are the correct possible structures.