Question

Given below are two statements:
Statement I: C–Cl bond is stronger in $\mathrm{CH_2 = CH{-}Cl}$ than in $\mathrm{CH_3{-}CH_2{-}Cl}$.
Statement II: The given optically active molecule, on hydrolysis, gives a solution that can rotate the plane polarized light.
In the light of the above statements, choose the correct answer from the options given below:

• A. Both Statement I and Statement II are false
• B. Statement I is true but Statement II is false
• C. Both Statement I and Statement II are true
• D. Statement I is false but Statement II is true
  \bigskip

Hint:

Resonance increases bond strength, and chirality is preserved if substitution does not cause racemization.

Answer 1

The Correct Option is C

Step 1: Analysing Statement I.
In vinyl chloride $\mathrm{(CH_2=CH{-}Cl)}$, the carbon bonded to chlorine is sp$^2$ hybridized. The C–Cl bond has partial double bond character due to resonance, making it stronger than the C–Cl bond in ethyl chloride $\mathrm{(CH_3{-}CH_2{-}Cl)}$, where carbon is sp$^3$ hybridized.
Hence, Statement I is true.
Step 2: Analysing Statement II.
The given molecule is optically active. On hydrolysis, substitution occurs without destroying chirality, producing a chiral alcohol. Hence, the resulting solution remains optically active and can rotate plane polarized light.
Thus, Statement II is true.
Step 3: Final conclusion.
Both Statement I and Statement II are true, corresponding to option (3).