An optically active alkyl halide, specifically -bromopentane, is subjected to a reaction with sodium hydrogen sulfide () dissolved in pure acetone. What is the explicit stereochemical designation and

Question

An optically active alkyl halide, specifically $(R)-2$ -bromopentane, is subjected to a reaction with sodium hydrogen sulfide ($NaSH$) dissolved in pure acetone. What is the explicit stereochemical designation and structural relationship of the major product relative to the starting reactant?

Prashant Kotian · Accepted Answer

Correct answer: A. The reaction utilizes a strong nucleophile () in a highly polar aprotic solvent (acetone) operating on a secondary alkyl halide. These precise conditions overwhelmingly favour the mechanism. The nucleophile executes a rigorous backside attack on the chiral carbon, displacing the bromide ion in a concerted step. This process forces the spatial arrangement to flip completely (Walden inversion), seamlessly converting the -configuration directly into the -configuration to yield optically pure -pentanethiol.

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