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Nucleophilic Substitution (sn1/sn2)

Mediumchemistry

Which substrate is expected to undergo SN1 reaction most readily in aqueous ethanol?

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About This Question

Subject
chemistry
Chapter
organic compounds containing halogens
Topic
nucleophilic substitution (sn1/sn2)
Difficulty
Medium
Year
2025
Tags
SN1Carbocation StabilityTertiary Halide

Solution

Correct Answer:

SN1 reaction rate depends on carbocation stability after leaving group departure. tert-Butyl chloride forms a tertiary carbocation, which is most stable among the options due to +I effect and hyperconjugation from three alkyl groups. Hence it undergoes SN1 fastest in polar protic medium.

This medium difficulty chemistry question is from the chapter organic compounds containing halogens, covering the topic of nucleophilic substitution (sn1/sn2). It appeared in the 2025 exam.

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