An optically active alcohol, -octan-2-ol, with a specific rotation , is reacted with an excess of in an inert solvent like dioxane (without pyridine). Upon isolation, the resulting 2-chlorooctane is e

Question

An optically active alcohol, $(R)$ -octan-2-ol, with a specific rotation $[\alpha]_D = -10.3^\circ$, is reacted with an excess of $SOCl_2$ in an inert solvent like dioxane (without pyridine). Upon isolation, the resulting 2-chlorooctane is examined in a polarimeter. Which of the following precisely describes its stereochemical profile?

Prashant Kotian · Accepted Answer

Correct answer: C. When an alcohol reacts with in the absence of a base (like pyridine), the reaction mechanism is (Substitution Nucleophilic internal). An alkyl chlorosulphite intermediate forms and then decomposes. The breaking of the bond and the making of the bond occur on the exact same face of the chiral carbon via an intimate ion pair or a cyclic transition state. This front-face delivery ensures that the spatial arrangement remains unchanged, strictly resulting in the retention of configuration ( -to- ). Note: Specific rotation values differ between distinct chemicals, so the exact number will change, but the configuration is retained.

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