Consider the reaction of $(R)\text{-2-bromobutane}$ with aqueous $\text{NaOH}$. What is the stereochemical outcome of the product?

Solution

1. The reaction of a secondary alkyl halide with a weak nucleophile like ${\text{OH}}^{-}$ in a polar protic solvent follows an ${\text{S}}_{\text{N}}1$ mechanism.
2. The rate-determining step involves the formation of a planar carbocation intermediate, ${\text{CH}}_3{\text{CH}}^{+}{\text{CH}}_2{\text{CH}}_3$.
3. The nucleophile can attack the carbocation from either side with equal probability.
4. This results in the formation of a racemic mixture of $(R)$ and $(S)$ isomers.
5. Hence the answer is (C).