The boiling point order is Alkynes > Alkene > Alkane
In alkane, more the surface area more will be the boiling point. So for the given compound, n-pentane, 2-methylbutane, 2,2-dimethylpropane, the surface area are in the order
Pentane > 2-methylbutane > 2,2-dimethylpropane.
So the given compounds exist wilth boiling point order as
Pentyne > Pentene > n-pentane > 2-methyl butane > 2,2 -dimethylpropane