This organic chemistry video tutorial provides the reaction mechanism between an alcohol with PBr3 or PCl3 (Phosphorous Trihalide) and SOCl2 (Thionyl Chloride) to produce alkyl halides such as an alkyl chloride or alkyl bromide. This video discusses the stereochemistry as well. PBr3 proceeds with an SN2 reaction mechanism with inversion of configuration. SOCl2 reacts with an SN2 mechanism when a mild base such as pyridine is used. Without Pyridine, it proceeds via a SNi mechanism or nucleophilic substitution with internal return where retention of configuration is observed. This video contains plenty of examples and practice problems.
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