What is the best choice of reagent to achieve the following transformation?

Question

Quizplus · Accepted Answer

The transformation involves the conversion of an alcohol to an alkyl chloride. The best reagent for this transformation is thionyl chloride (SOCl2) in the presence of pyridine as it is a commonly used reagent for this conversion and has high selectivity and good yield. HCl is not a strong enough acid to react with the alcohol and will not result in the desired product. Cl₂ is not a known reagent and cannot be used for this transformation. HOCl is not a commonly used reagent for this transformation and will not produce good yields.

What Is the Best Choice of Reagent to Achieve the Following