Question
Which of the following nucleophiles, in conjunction with heat and water as a byproduct, is most probable in the following substitution reaction and by which mechanism?


CH нс— сн, CI CH Н,с- сн, Он 8о
OH20, SN1 CH30, SN2 HI, SN2 HCI, SN1 OH, SN1
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Answer #1

We can see that in given reaction -OH is replaced by -Cl. So the only nucleophile that can bring about this conversion is HCl and because the reactant is a tertiary alcohol (the C to which -OH is attached is attached to 3 carbons) so the mechanism by which this nucleophilic substitution reaction proceeds is SN​​​​​​1 (Substitution Nucleophilic Unimolecular).

So the correct answer is option fourth (HCl, SN​​​​​​1)

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