For 3-chloro-2-butanol, you have but-2-ene --> addition reaction with Cl2 --> substitution of 2,3-dichloro-butane with hydroxide ion (from strong base e.g. NaOH)?
So you have molecules where multiple functional groups are being added so the way you want to do these types of questions is think about how you could make each of them individually
For the 3-chlorobutan-2-ol you can use but-2-ene do a substitution reaction in presence of Uv light with chlorine gas. That will make 2-chlorobut-2-ene
Then react that with water and dilute Sulfuric acid catalyst and you make the 3-chlorobutan-2-ol
use pent-2-ene do an addition reaction with chlorine gas. This will make 2,3-dichloropentane. Then add sodium hydroxide excess and a substitution reaction will occur giving you Pentan-2,3-diol
use pent-2-ene do an addition reaction with chlorine gas. This will make 2,3-dichloropentane. Then add sodium hydroxide excess and a substitution reaction will occur giving you Pentan-2,3-diol