AAMC: Conversion of alcohol to alkyl halide SN1 or SN2?

[cfx]

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One of the discretes in AAMC practice test 7 asks:

Which of the following is most readily prepared by reaction between the corresponding alcohol and concentrated HCl?

two of the answer choices:

Methyl chloride
tert-butyl chloride

I answered methyl chloride, while the actual answer was tert-butyl chloride.

I was under the impression that this substitution would occur via protonation of the alcohol, followed by SN2. I looked it up, and it appears that it can occur via SN1 OR SN2, depending on the substrate.

So what's the rationale for tert-butyl chloride (SN1) over methyl chloride (SN2)?

 

[RogueUnicorn]

you're in a protic solvent

 

[cfx]

you're in a protic solvent

Ah, can't believe I didn't think of this. Thanks.

 

[RogueUnicorn]

🙂 happens to the best of us