During the specific reaction of an optically active secondary alcohol with neat operating strictly v — Haloalkanes and Haloarenes Chemistry Question
Question
During the specific reaction of an optically active secondary alcohol with neat $SOCl_2$ operating strictly via the $S_Ni$ mechanism, what critical and observable functional roles do the participating chemical species play?
💡 Solution & Explanation
A) True. The first rapid step is the formation of the alkyl chlorosulphite. B) True. The defining feature of $S_Ni$ is the internal delivery of the nucleophile from within the leaving group cluster. C) False. The $S_Ni$ mechanism absolutely forbids the formation of a free, planar carbocation; if a free carbocation formed, racemisation would occur. Instead, an intimate ion pair or cyclic transition state maintains the geometry. D) True. The front-face cyclic transition state structurally forbids inversion, strictly enforcing retention.