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Which of the following alcohols undergoes the fastest reaction with concentrated HCl in the presence of anhydrous ZnCl2?

1. 2-Butanol
2. 2-Methylpropan-2-ol
3. 2-Methylpropanol
4. 1-Butanol

Correct answer: 2-Methylpropan-2-ol

Solution

With conc. HCl/anhydrous ZnCl2 (Lucas reagent) the reaction goes via a carbocation (SN1). 2-Methylpropan-2-ol is tertiary and forms the most stable carbocation, so it reacts fastest.

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