How can you predict whether primary, secondary, and tertiary alcohol undergoes halogenation?
How else but by experiment............?
Chemistry is an experimental science. Of course, we attempt to make some sense of the experimental results by invoking a theoretical framework, however experiment is king. And we don't really know what you want to do in the reaction: replace the hydroxyl group by halogen; eliminate the hydroxyl group, and then hydrohalogenate the olefin.........?