Haloalkanes and HaloareneshardNUMERICAL

How many total distinct optically active stereoisomers are geometrically formed when a pure sample oHaloalkanes and Haloarenes Chemistry Question

Question

How many total distinct optically active stereoisomers are geometrically formed when a pure sample of $(R)-2$ -bromobutane undergoes an idealized pure $S_N1$ hydrolysis reaction (assuming theoretical 100% racemisation without any specific solvent-caging effects)?

Answer: 2

💡 Solution & Explanation

An idealized $S_N1$ reaction on a pure chiral substrate proceeds through a perfectly planar carbocation. The incoming nucleophile attacks from both faces equally. This results in the formation of both the $(R)$ -enantiomer and the $(S)$ -enantiomer of 2-butanol. Since both the $(R)$ and $(S)$ forms are individually distinct optically active stereoisomers, exactly 2 active isomers are formed (even though they exist as a racemic mixture).

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