information:extraction, structural:reformatting
Nucleophilic substitution

Tertiary alcohols react with hydrochloric acid to produce tertiary alkyl chloride. Primary and secondary alcohols are converted to the corresponding chlorides using thionyl chloride and various phosphorus chloride reagents.

Primary and secondary alcohols, likewise, convert to alkyl bromides using phosphorus tribromide, for example:

In the Barton-McCombie deoxygenation an alcohol is deoxygenated to an alkane with tributyltin hydride or a trimethylborane -water complex in a radical substitution reaction.