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Alkyl halides and Alcohols Interconversions

Answers for Exercise

Interconversion of Alcohols and Alkyl Halides

Instead of PCl5 other reagents have been used.

Try to complete the equations. If PCl3 is used the side product is different( H3PO3 ). PCl5 reactions are somewhat messy, it is usually difficult to separate the side products, a reagent that is toxic but gives product in high yield is Thionyl chloride ( SOCl2). The side products in this case are both gases, therefore can be easily eliminated, they are SO2 and HCl.

PBr3 reacts similar to PCl3, it can replace the -OH with -Br.

Heating with NaOH is a useful method of replacing the halogen of an alkyl halide like ethyl bromide with -OH. Can HOH be used for the purpose? If not why not?

Mechanism of nucleophilic substitution
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