When an optically pure sample of -bromobutane undergoes an idealized pure hydrolysis, the resulting — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

In an idealized $S_N1$ reaction, the rate-determining loss of the leaving group generates a free, $sp^2$ hybridized carbocation. Because the empty $p$ -orbital is planar, the incoming nucleophile ($H_2O$) has an equal statistical probability of attacking from the top face (yielding one enantiomer) or the bottom face (yielding the opposite enantiomer). This 50:50 attack intrinsically generates a racemic mixture, completely neutralizing the net optical activity.