Refluxing an alcohol with SOCl2 or PCl3 or PCl5 converts it to what?

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Multiple Choice

Refluxing an alcohol with SOCl2 or PCl3 or PCl5 converts it to what?

The main idea is substitution of the hydroxyl group with chlorine to make a haloalkane. When you reflux an alcohol with SOCl2, PCl3, or PCl5, the OH is converted into a better leaving group and chloride ion from the reagent attacks the carbon, replacing the OH with Cl. This gives an alkyl chloride (haloalkane) as the product. Heating helps drive the reaction forward. The byproducts depend on the reagent (SOCl2 releases SO2 and HCl, while PCl3/PCl5 generate related phosphorus oxychlorides and HCl). So, the alcohol is converted to a haloalkane, not back to alcohol or to an alkene under these conditions.

The main idea is substitution of the hydroxyl group with chlorine to make a haloalkane. When you reflux an alcohol with SOCl2, PCl3, or PCl5, the OH is converted into a better leaving group and chloride ion from the reagent attacks the carbon, replacing the OH with Cl. This gives an alkyl chloride (haloalkane) as the product. Heating helps drive the reaction forward. The byproducts depend on the reagent (SOCl2 releases SO2 and HCl, while PCl3/PCl5 generate related phosphorus oxychlorides and HCl). So, the alcohol is converted to a haloalkane, not back to alcohol or to an alkene under these conditions.

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