SOCl2/ pyridine
used to replace OH with Cl (No shifts)
SOCl2 (thionyl chloride) in pyridine is a commonly used reagent combination in organic chemistry for the conversion of alcohols to chlorides. In this reaction, SOCl2 reacts with the alcohol to form an alkyl chloride and hydrogen chloride gas. Pyridine is added as a base to neutralize the HCl gas and prevent it from interfering with the reaction.
The mechanism of the reaction involves the formation of an intermediate, a mixed anhydride, between the alcohol and the thionyl chloride. The pyridine serves as a nucleophile and attacks the intermediate to form the alkyl chloride and regenerate the starting thionyl chloride. The pyridine also neutralizes any HCl gas that is formed.
Overall, this reaction is a useful method for synthesizing alkyl chlorides from alcohols. However, it should be noted that thionyl chloride is a highly reactive and toxic compound that should be handled with care. Additionally, the use of pyridine can lead to the formation of pyridine-HCl salt, which can be difficult to separate from the desired product and can require additional purification steps.
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