2-Hydroxycyclopentanone
3-Hydroxypentan-2-one
1-Pentanol
4-Hydroxypentan-2-one
3-Hydroxypentan-2-one and 4-Hydroxypentan-2-one will most readily be dehydrated to give alkene under acidic condition. This will lead to formation of α−βunsaturated ketone. But out of both 4-Hydroxypentan-2-one will most readily be dehydrate to give alkene under acidic condition. Note: Dehydration of 2-Hydroxycyclopentanone will lead to C=C double bond in 5 member ring that will cause strain and product is less likely to be formed.