Draw a stepwise mechanism for the chlorination of 2−phenylethanol with thionyl chloride in pyridine:

Producto formed 2-phenylchloroethane + HCl + SO2

Explanation:

The mechanism of reaction with SOCl2 (Thionyl chloride), is a reaction that it's taking place with primary and secondary alcohols. This is because primary alcohols are very unstable, so the SOCl2 is really useful when we want to take a SN2 reaction. The pyridine works as solvent of the reaction and helps to retain the chlorine ions in solution.

The first step is a nucleophylic attack of the OH to the sulfur atom. Then, the chlorine leaves the molecule and the pyridine get it. Then, the chlorine substract the atom of hydrogen from the OH. Finally the lone pair of the oxygen go down, and the other chlorine leaves the molecule, (Because primary alcohols are very unstable) and finally, the Chlorine attacks again, and the SOCl2 leaves the molecule.

In the picture you have the mechanism:

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