A synthetic chemist must synthesize an alkyl halide using an alcohol and HCl. While she does not have many available solvents, she concludes that with the right reaction conditions, the alcohol can serve as both the substrate and the solvent. Which of the following alcohols would be best suited for this task?
A. Ethanol
B. Isopropyl alcohol
C. Tert-butyl alcohol
D. All alcohols react equally to form alkyl halides
Click for Explanation
C is correct. The question stem states that the chemist will be using an alcohol as a solvent, which is a protic solvent as it can form hydrogen bonds. HCl in solution will dissociate to form the chloride nucleophile and hydrogen ions. These reaction conditions will favor a Sn1 reaction mechanism. Under these conditions, the reactivity of substrates follows the trend: tertiary > secondary > primary > methyl. Thus, we are looking for a tertiary alcohol, which is consistent with tert-butyl alcohol. Isopropyl alcohol is a secondary alcohol and ethanol is a primary alcohol.
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