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NEET CHEMISTRYMedium

A compound that does not undergo SN1S_N1 reaction with OH\text{OH}^- is:

A

CH2=CHCH2Cl\text{CH}_2=\text{CH}-\text{CH}_2\text{Cl}

B

C6H5CH2Cl\text{C}_6\text{H}_5\text{CH}_2\text{Cl}

C

(CH3)3CCl(\text{CH}_3)_3\text{CCl}

D

CH2=CHCl\text{CH}_2=\text{CH}-\text{Cl}

Step-by-Step Solution

In an SN1S_N1 reaction, the rate-determining step is the formation of a carbocation intermediate. The reactivity of the compound towards SN1S_N1 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=CHC+H2\text{CH}_2=\text{CH}-\overset{+}{\text{C}}\text{H}_2), which is highly stabilized by resonance .
  • Option B (Benzyl chloride): Forms a benzyl carbocation (C6H5C+H2\text{C}_6\text{H}_5\overset{+}{\text{C}}\text{H}_2), which is highly stabilized by resonance through the benzene ring .
  • Option C (tert-Butyl chloride): Forms a tertiary (33^\circ) carbocation ((CH3)3C+(\text{CH}_3)_3\overset{+}{\text{C}}), which is stabilized by the +I+I effect and extensive hyperconjugation (due to 9 α\alpha-hydrogens) .
  • Option D (Vinyl chloride): Forms a vinyl cation (CH2=C+H\text{CH}_2=\overset{+}{\text{C}}\text{H}). This intermediate is highly unstable because the positive charge resides on a highly electronegative spsp-hybridized carbon atom. Additionally, the CCl\text{C}-\text{Cl} bond possesses a partial double bond character due to the delocalisation of chlorine's lone pair with the π\pi-bond, making it very difficult to break heterolytically .

Therefore, vinyl chloride does not undergo an SN1S_N1 reaction.

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