Haloalkanes and HaloareneshardMCQ MULTIPLE

Which of the following advanced mechanistic statements correctly validate the intricacies of transfoHaloalkanes and Haloarenes Chemistry Question

Question

Which of the following advanced mechanistic statements correctly validate the intricacies of transforming chiral alcohols into alkyl chlorides uniquely utilizing Darzens' procedure ($SOCl_2$ reagent)?

Answer: A,B,C

💡 Solution & Explanation

A) True. The $S_Ni$ mechanism relies on an intramolecular delivery providing front-face retention. B) True. The $R-OH + SOCl_2$ reaction rapidly yields the $R-O-S(=O)-Cl$ ester. C) True. Pyridine reacts to form pyridinium chloride, unleashing free $Cl^-$ which promptly performs an $S_N2$ backside attack before internal collapse can occur, inverting the stereocenter. D) False. The gaseous nature of the $SO_2$ and $HCl$ byproducts allows them to easily escape, making this process the absolute best method for obtaining ultra-pure alkyl chlorides.

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