Question

If a molecule can hydrogen bond does it guarantee that it will have a higher boiling point than a molecule that cannot?

Answer 1

A molecule that can h-bond will not always necessarily and does not have guarantee to have a higher boiling point than one than cannot have h-bond.
we can take an example of Pentan-2-one that cannot h-bond but instead of this it  has a high boiling point that is 102.3 °C, while propan-1-ol can h-bond but it has a boiling point of 97.2°C, that is lower than the boiling point of Pentan-2-one.