Haloalkanes and Haloarenes Part 2

Concept:Statement I involves the effect of resonance on bond strength in vinyl halides. Statement II involves the retention of optical activity after hydrolysis of a chiral alkyl halide.Explanation:In $\mathrm{CH_2=CH-Cl}$, the lone pair on chlorine undergoes resonance with the carbon-carbon double bond. This gives the $\mathrm{C-Cl}$ bond partial double bond character, making it stronger than the pure single $\mathrm{C-Cl}$ bond in $\mathrm{CH_3-CH_2-Cl}$. Therefore Statement I is true.The given optically active molecule is a chiral alkyl halide (for example, 2-chlorobutane). Upon hydrolysis, the reaction typically proceeds via an $\mathrm{S_N1}$ mechanism due to the formation of a carbocation intermediate. The nucleophile ($\mathrm{OH^-}$) can attack from either side of the planar carbocation, leading to racemization. The resulting product is a racemic mixture, which is optically inactive and does not rotate plane polarized light. Hence Statement II is false.Answer:Statement I is true but Statement II is false. Correct option is B.