See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

**Analysis of Hydrolysis Reactivity** Hydrolysis reactivity of alkyl halides depends on the stability of the carbocation intermediate formed during the $S_N1$ mechanism. **Evaluating each option:** **(A) $PhCH_2Cl$ (Benzyl chloride):** Forms a benzyl carbocation $PhCH_2^+$, which is stabilized by resonance with the benzene ring → **highly reactive** **(B) $CH_2=CHCH_2Cl$ (Allyl chloride):** Forms an allyl carbocation $CH_2=CHCH_2^+$, stabilized by resonance → **highly reactive** **(C) $(CH_3)_3C-Cl$ (tert-Butyl chloride):** Forms a tertiary carbocation $(CH_3)_3C^+$, stabilized by hyperconjugation and inductive effects → **very reactive** **(D) Norbornyl chloride (bicyclic structure):** Forms a norbornyl carbocation that is **extremely hindered** sterically. The bicyclic framework creates rigid 3D geometry where the back side of the C-Cl bond is blocked by the bridge, preventing proper orbital overlap needed for carbocation formation. Additionally, any carbocation intermediate would be highly strained in this rigid system. **Conclusion:** Option **(D)** is least reactive because steric hindrance from the bicyclic geometry severely impedes both the departure of $Cl^-$ and stabilization of the resulting carbocation, making hydrolysis extremely slow.