Boiling point confusion

[Aanya Munagala 1D]

Hello,

How do you know which molecule will have a higher boiling point when one is significantly larger, but the other has hydrogen bonding. I was looking at two different practice sheets from two different TAs and one of them said that C10H22 would have a higher boiling point than CH3OH due to LDFs but in the other practice they said CH3OH would have a higher bp than CH3CH2CH2CH2CH3 because of its hydrogen bonding. So how do you know when one force is stronger?

Thanks!

[ZacharyKrauss1A]

Well the second example you cite has half the carbons that the first molecule has meaning it has significantly less london dispersion forces. I would say on a test it would be pretty clear which is going to have more impact and it would not be something that it close.