How to determine which hydrogen becomes deprotonated

[Sylvia Zhang 2L]

Hello, I was wondering why the compound C6H5OH deprotonates to C6H5O instead of C6H4OH. Also, is there any way to determine which hydrogen becomes removed?

[Lillian Ott 3D]

I find it helpful to think about the lewis structure of the compound in figuring out which hydrogen will be donated. C6H5OH is a ring of carbon molecules with hydrogens attached to them, with one carbon being attached to an OH. The carbon being written as the first element in C6H5OH implies it is the central atom, and we can assume the hydrogens will be distributed bonded to the carbon atoms. The OH being written on the end (rather than something like C6H6O) implies that O is bonded to H, and this hydroxyl group is bonded to a central carbon atom, making the hydrogen more likely to leave this group than being attached directly to a carbon.