Final answer:
Hexanoic acid has the highest boiling point due to its ability to form strong hydrogen bonds and dimerize, followed by n-hexanol which can also form hydrogen bonds but cannot dimerize, and finally, hexane with the lowest boiling point as it can only participate in van der Waals forces.
Step-by-step explanation:
The boiling point of a compound is influenced by the molecular weight and the type of intermolecular forces present. The compounds in question are 1-hecanol, n-hexanol, hexane, and hexanoic acid. When ranking these compounds by boiling point, we consider their structures and the strength of the intermolecular forces each can participate in.
Hexanoic acid will have the highest boiling point due to its ability to form hydrogen bonds and also because it can dimerize, increasing the effective molecular size. n-Hexanol comes next, as it can form hydrogen bonds, but cannot dimerize like hexanoic acid. 1-Hecanol is likely a typo for 1-hexanol, which would be the same as n-hexanol. Hexane will have the lowest boiling point because it can only participate in weak van der Waals forces due to its nonpolar nature.
Therefore, the correct ranking from highest to lowest boiling point should be:
- Hexanoic acid
- n-Hexanol or 1-Hecanol (assumed to be 1-hexanol)
- Hexane