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Question 36 of 48

Q.In presence of aqueous alkali which of the following will take part easily in SN1 reaction?

(a) CH3CH2CH2Cl
(b) (CH3)2CHCH2Cl
(c) CH3-CH2CH(CH3)-Cl
(d) (CH3)3C-Cl
West Bengal WbchseWest Bengal HS (WBCHSE) Board 2022MCQ· 1mImportance★★★★★
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SN1 reactivity depends on carbocation stability; a tertiary halide forms the most stable (tertiary) carbocation, so it reacts fastest by the SN1 pathway.

Reasoning: In an SN1 reaction, the rate-determining step is the formation of a carbocation intermediate after the leaving group (Cl-) departs. The more stable this carbocation, the faster the SN1 reaction proceeds. Carbocation stability order: 3° > 2° > 1° (due to increasing hyperconjugation and +I inductive electron donation from more alkyl groups).

Among the given options:

  • (a) CH3CH2CH2Cl — 1° halide, forms an unstable 1° carbocation, reacts very slowly by SN1 (favours SN2 instead).
  • (b) (CH3)2CHCH2Cl — 1° halide (neopentyl-like/isobutyl), also a poor SN1 substrate. …

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