Boiling point of a substance is determined by the strength of the intermolecular forces. In hydrocarbons, the primary intermolecular force is the London dispersion force, which increases with the size and shape of the molecule.

Longer, straight chain hydrocarbons have higher boiling points because they have larger surface areas leading to stronger London dispersion forces. Branched hydrocarbons have lower boiling points because their shape leads to a smaller surface area, reducing the strength of the London dispersion forces.

Here is the order of the hydrocarbons from lowest to highest boiling point:

1. 3,3-dimethylpentane: This is the most branched hydrocarbon, leading to the smallest surface area and the weakest London dispersion forces.
2. 2-methylpentane: This is less branched than 3,3-dimethylpentane but more branched than the straight chain hydrocarbons, leading to stronger London dispersion forces.
3. 2-methylhexane: This is a branched hydrocarbon but has a longer chain than 2-methylpentane, leading to stronger London dispersion forces.
4. Hexane: This is a straight chain hydrocarbon with six carbons, leading to stronger London dispersion forces than the branched hydrocarbons.
5. Heptane: This is the longest straight chain hydrocarbon with seven carbons, leading to the strongest London dispersion forces and the highest boiling point.

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