Worked example 1
Propane (44 g/mol, nonpolar) boils at -42 °C and acetaldehyde (44 g/mol, polar) at 20. Explain.
Try it first: Note what is the same before looking for what is different.
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What you'll be able to do: Identify dipole-dipole and ion-dipole interactions and rank them against dispersion.
Best after: London Dispersion Forces
Once a molecule has a permanent dipole, its neighbours no longer rely on fleeting fluctuations. Permanent charges line up, and the attraction gets stronger and more predictable.
These are recommended, not required. You can start this lesson at any time.
A polar molecule has a positive end and a negative end that do not move. Neighbours orient so that opposite ends face each other. The attraction is stronger than dispersion for molecules of similar size, typically a few kJ/mol up to about 25 kJ/mol.
Dipole-dipole only decides the outcome when the molecules being compared have similar electron counts. Propane and acetaldehyde have similar masses, but acetaldehyde is polar and boils about 62 degrees higher.
A full ionic charge attracts the partial charge on a polar molecule far more strongly than one partial charge attracts another. When NaCl dissolves, the partial negative oxygen of water surrounds Na⁺ and the partial positive hydrogens surround Cl⁻.
For molecules of comparable size: dispersion < dipole-dipole < hydrogen bonding < ion-dipole < ionic bonding. Treat the list as a guide, since a very large nonpolar molecule can outweigh a small polar one.
Ion-dipole attraction depends on an ion's charge and the distance at which a polar molecule can approach it. At the same charge, a smaller ion has greater charge density and can attract nearby water molecules more strongly. Hydration enthalpy also depends on the number and arrangement of water molecules, so a simple size rule is a controlled comparison, not a complete prediction of solubility.
Attraction between the permanent dipoles of neighbouring polar molecules.
Attraction between an ion and the oppositely charged end of a polar molecule.
Dispersion < dipole-dipole < hydrogen bonding < ion-dipole at comparable size.
Dissolving an ionic solid in water replaces lattice attractions with ion-dipole attractions.
Propane (44 g/mol, nonpolar) boils at -42 °C and acetaldehyde (44 g/mol, polar) at 20. Explain.
Try it first: Note what is the same before looking for what is different.
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Describe the interactions when MgCl₂ dissolves in water and why Mg²⁺ is hydrated more strongly than Na⁺.
Try it first: Draw one water molecule near a cation and label its partial charges.
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Compare the strength of local ion-dipole attractions when Li⁺ and K⁺ each become hydrated.
Try it first: Both ions have charge +1, so isolate their size difference.
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Why it's wrong: Symmetric molecules such as CCl₄ have cancelling bond dipoles and no net dipole.
Check instead: Check the geometry and confirm a net dipole before claiming dipole-dipole.
Why it's wrong: Dispersion scales with electron count and can dominate entirely.
Check instead: Compare electron counts first, then polarity.
Why it's wrong: One partner carries a full charge, not a partial one.
Check instead: Name it ion-dipole whenever an ion is involved.
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Polar molecules attract each other head to tail through dipole-dipole forces, which add to the dispersion always present. When an ion meets a polar molecule the attraction is stronger still, and ion-dipole forces are what make ionic compounds dissolve in water.
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