Optically pure (S)-3-methylhexane is treated with $\mathrm{Br}{}_2$ in light. The major monobromo product, 3-bromo-3-methylhexane, is obtained as

Bromine radicals are highly selective for the tertiary C-H at C3. Removal of that H gives a planar (sp2) tertiary radical that has lost the stereochemical information. Bromine can be delivered to either face with equal probability, so the product is a 1 : 1 mixture of enantiomers. It is a racemate, not a meso compound, since the compound has only one stereocentre.