In terms of intermolecular forces, explain why we see this general trend with formula masses

Which of the molecules below has the highest boiling point? Explain your choice in terms of intermolecular forces, listing all types of intermolecular forces involved.

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1-pentanol propyl ethyl ether 1,5-pentanediol

Question 1. Which of the three molecules is most attracted to the mobile phase? Explain your reasoning in terms of intermolecular forces.

Question 2. Which molecule is most attracted to the stationary phase? Explain your reasoning in terms of intermolecular forces.

Question 3. In what order will the three molecules exit (or “elude from”) the column?