SOCl2/ pyridine
used to replace OH with Cl (No shifts)
SOCl2/pyridine is a common reagent mixture that is often used in organic chemistry for various transformations, such as the conversion of alcohols into alkyl chlorides or carboxylic acids into acid chlorides.
SOCl2 is an abbreviation for thionyl chloride, which is a highly reactive compound that is commonly used for the conversion of alcohols into alkyl chlorides. It works by reacting with the hydroxyl group of the alcohol to form a chlorosulfite intermediate. This intermediate then undergoes elimination of sulfur dioxide to yield the alkyl chloride.
Pyridine, on the other hand, is a basic compound that is often used as a solvent or catalyst in various organic reactions. In the case of SOCl2/pyridine reagent mixture, pyridine acts as a catalyst by facilitating the reaction between SOCl2 and the alcohol.
When mixed together, SOCl2 and pyridine react to form pyridinium hydrogen sulfite as an intermediate. This intermediate then proceeds to react with the alcohol, forming the chlorosulfite intermediate. Under elimination of sulfur dioxide, the final product, alkyl chloride is obtained.
Overall, the SOCl2/pyridine reagent mixture is a useful tool for the conversion of alcohols to alkyl chlorides or carboxylic acids into acid chlorides. However, as SOCl2 is a highly reactive and corrosive compound, it needs to be handled with care with proper safety measures.
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