How can alcohols be converted into alkyl halides using hydrogen halides?

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Alkyl halides are commonly synthesized from alcohols through a substitution reaction in which a halogen atom replaces the hydroxyl group (-OH).1

To convert alcohols into alkyl halides using hydrogen halides, the alcohol is reacted with hydrochloric (HCl), hydrobromic (HBr), or hydroiodic (HI) acid. This process is most effective when using tertiary alcohols, which generally provide the best yields.1

While hydrogen halides are effective reagents for this transformation, other compounds such as thionyl chloride (SOCl2), phosphorus tribromide (PBr3), and phosphorus triiodide (generated from phosphorus and iodine) are also frequently employed to produce alkyl chlorides, bromides, and iodides, respectively.1