Solubility of C5H11OH and C5H11Cl
In the case of the water solubility what you want to know is how powerful the secondary interaction  of the compound that you are going to dissolve with  water?If the compound that you wish to dissolve have hydrogen bonding then it's definitely dissolve in water .It does not mean others  are  insoluble  in water.

But  the compounds do not have hydrogen bonding are  less soluble in water when compared to    the ones which have hydrogen bonding.Because ones which have hydrogen bonding interact with water molecules easily than others which do not have hydrogen bonding 

Now take a look at the image   below, 



It shows two water molecules  which posses the hydrogen bonding interaction. 

Now give the eye on compounds that you have got, 

The  compounds that you going to dissolve  may form  interaction force  with water as above image. If that interaction force is hydrogen bonding ($\ce{C5H11OH}$) then it's solubility is greater than ones which do not have hydrogen bonding($\ce{C5H11Cl}$) (dipole dipole interactions)

So because of that solubility of $\ce{C5H11Cl}$ is less than the solubility of ($\ce{C5H11OH}$) with water.

Then the bottom line is ,the solubility of a compound is vary according the  secondary interaction between the solute and solvent.In the case of water acting as  the solvent solubility is highest in  compounds which having H bonding , than which haaving dipole-dipole forces and  weak dispersion forces.