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Chapter 22: Problem 5

If you had a group of hydrocarbons, what structural features would you look at to rank the hydrocarbons in order of increasing boiling point?

Short Answer

Expert verified
To rank hydrocarbons in order of increasing boiling point, consider the following factors: type of hydrocarbon (alkane, alkene, or alkyne), molecular size and weight, structural shape, degree of branching, and intermolecular forces present (primarily London dispersion forces). Larger, heavier, and more linear molecules with stronger intermolecular forces will generally have higher boiling points.

Step by step solution

01

Identify the type of hydrocarbon

Determine if the hydrocarbon is an alkane (single bonds), alkene (double bonds), or alkyne (triple bonds). In general, as the number of bonds increases, the boiling point also increases due to increased strength of intermolecular forces.
02

Determine the molecular size and weight

Larger and heavier molecules have higher boiling points, as more energy is needed to break the intermolecular Van der Waals forces between the molecules. Count the number of carbon atoms in the hydrocarbon and compare their molecular weights to help rank the boiling points.
03

Evaluate the effect of structural shape

The shape of the molecule affects the strength of its intermolecular forces. Linear or more extended molecules have larger surface areas and therefore stronger forces, resulting in higher boiling points. Cyclic forms can also have higher boiling points due to their rigid structures. Identify the shape of each hydrocarbon to account for this factor in ranking their boiling points.
04

Assess the impact of molecular branching

Molecules with more branching or more compact structures have a reduced surface area, which reduces the strength of intermolecular forces and lowers the boiling point. Compare the degree of branching in each hydrocarbon and rank them accordingly.
05

Consider intermolecular forces

Hydrocarbons are primarily affected by London dispersion forces, which are influenced by the size and shape of the molecule. Heavier and larger molecules have stronger dispersion forces and therefore higher boiling points. Additionally, check for any other intermolecular forces that may contribute to the overall boiling point, such as hydrogen bonding, which can occur if there are functional groups present in the hydrocarbon.
06

Rank the hydrocarbons

Using the information gathered in Steps 1 to 5, rank the hydrocarbons in order of their boiling points. Consider the type of hydrocarbon, molecular size and weight, structural shape, the presence of branching, and any intermolecular forces present. Ranks should increase in order of increasing boiling points based on these factors.

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