A researcher intends to convert an optically active secondary alcohol into its corresponding alkyl chloride. They perform two parallel experiments: Experiment 1 uses exclusively, while Experiment 2 us

Question

A researcher intends to convert an optically active secondary alcohol into its corresponding alkyl chloride. They perform two parallel experiments: Experiment 1 uses $SOCl_2$ exclusively, while Experiment 2 uses $SOCl_2$ mixed with an equimolar amount of pyridine. Which of the following statements correctly distinguish the two reactions?

Prashant Kotian · Accepted Answer

Correct answer: A,B. A) True. In Exp 1 (no base), the mechanism relies on an internal cyclic transition state providing retention. B) True. In Exp 2, pyridine forms pyridinium chloride, providing free which performs a backside attack, causing inversion. C) False. They yield opposite stereoisomers (Exp 1 = retention; Exp 2 = inversion). D) False. The alkyl chlorosulphite ester intermediate is formed initially in both reactions; it is the subsequent decomposition step that diverges based on the presence of the free nucleophile.

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