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For eg : would the reaction of 3-methylbut-2-en-1-ol with HBr follow SN1 mechanism due to stability of your intermediate carbocation stability or SN2 due to the compound being primary alcohol and good nucleophilic. Also please correct me if I got something wrong.

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It will follow SN1 as the intermediate carbocation formed is resonance stabilised.

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  • $\begingroup$ So should we consider that the stability of intermediate is key factor in deciding mechanism. $\endgroup$ – Preet Bhati May 4 at 5:33
  • $\begingroup$ It's one of the factors. For example : 2° alkyl halide can undergo solvolysis by SN1 ( in aqueous medium) as well as SN2 pathway (with alcohol and amines) $\endgroup$ – Arshiya May 4 at 5:58

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