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I think typically the dipole dipole is stronger mainly because it is only formed when there are permanent poles in molecules. In comparison, dispersion forces are due to instantaneous distortions of the electron cloud and can be observed in all molecules. I would imagine that there would be some molecules with a large enough electron cloud that would lead to a stronger dispersion force than a dipole dipole though. The dipole dipole interactions have a set range while the dispersion forces have a much larger range of strength, depending on the size of the electron cloud.
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