Optically pure (R)-2-bromooctane reacts with a high concentration of OH- in aqueous acetone purely by the S_N2 pathway. The product is

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Optically pure $(R)$ -2-bromooctane reacts with a high concentration of $OH X^{-}$ in aqueous acetone purely by the $S_{N} 2$ pathway. The product is

Backside attack gives inversion (Walden inversion). Priorities in the bromide are

Br > C X_{6} H X_{13} > CH X_{3} > H

and in the alcohol

OH > C X_{6} H X_{13} > CH X_{3} > H

, the same order, so the descriptor changes from

R

S

. The product is

(S)

-octan-2-ol.