The free radical monochlorination of (S)-2-chlorobutane gives

The absolute configurations of the products are as follows,

${\mathrm{CH}}_3{\mathrm{CHClCH}}_2{\mathrm{CH}}_3⟶\underset{R}{⟶}{\mathrm{ClCH}}_2{\mathrm{CHClCH}}_2{\mathrm{CH}}_3+{\mathrm{CH}}_3\mathrm{C}\left({\mathrm{Cl}}_2\right){\mathrm{CH}}_2{\mathrm{CH}}_3$$+{\mathrm{CH}}_3{\mathrm{CHClCHClCH}}_3+{\mathrm{CH}}_3{\mathrm{CHClCH}}_2{\mathrm{CH}}_2\mathrm{Cl}$