In an SN1 reaction, the rate-determining step is the formation of a carbocation intermediate. The reactivity of the compound towards SN1 depends entirely on the stability of the carbocation formed .
Let us evaluate the carbocations formed by the given options:
- Option A (Allyl chloride): Forms an allyl carbocation (CH2=CH−C+H2), which is highly stabilized by resonance .
- Option B (Benzyl chloride): Forms a benzyl carbocation (C6H5C+H2), which is highly stabilized by resonance through the benzene ring .
- Option C (tert-Butyl chloride): Forms a tertiary (3∘) carbocation ((CH3)3C+), which is stabilized by the +I effect and extensive hyperconjugation (due to 9 α-hydrogens) .
- Option D (Vinyl chloride): Forms a vinyl cation (CH2=C+H). This intermediate is highly unstable because the positive charge resides on a highly electronegative sp-hybridized carbon atom. Additionally, the C−Cl bond possesses a partial double bond character due to the delocalisation of chlorine's lone pair with the π-bond, making it very difficult to break heterolytically .
Therefore, vinyl chloride does not undergo an SN1 reaction.