Other Methods Used to Convert Alcohols into Alkyl Halides

2 OTHER METHODS USED TO CONVERT ALCOHOLS INTO ALKYL HALIDES 

Alcohols are inexpensive and readily available compounds, but they do not undergo nucleophihc substitution because the HO group is too basic to be displaced by a nucleophile (Section 11.1). Chemists, therefore, need ways to convert readily available but unreactive alcohols into reactive alkyl haUdes that can be used as starting materials for the preparation of a wide variety of organic compounds (Section 9.2). 

We have just seen that an alcohol can be converted into an alkyl halide by treating it with a hydrogen halide. Better yields of the alkyl halide are obtained and carbocation rearrangements can be avoided if a phosphorus trihalide (PCI3 or PBr3) or thionyl chloride (SOCI2) is used instead. 

These reagents all act in the same way they convert the alcohol into an intermediate with a leaving group that is readily displaced by a halide ion. 

MECHANISM FOR THE CONVERSION OF AN ALCOHOL INTO AN ALKYL BROMIDE (OR ALKYL CHLORIDE) USING PBrs (OR PCI3) 

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Other Methods Used To Convert Alcohols into Alkyl Halides 487... 

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