kdashc
Your calculations are correct, but are somewhat misleading.
with a 50/50 volume mixture at 50 psia the bubble point is 137°F. at 100°F you are below the bubble point, meaning that everything will condensate.
Yes the vapor fraction in equilibrium has about the composition that you indicate, but there is none of it.
At this pressure, as soon as your are below the temperature of 137°F, there is no vapor phase, in terms of quantity.
When you cool down from 200°F you will reach the so call dew point, at a temperature lower than 200°F but greater than 137°F, components will start condensing, and the first drops of condensate will have a compostion much richer in the heavy component (hexane) than the original feed mixture.
I hope this is clear to you.