Which of the following advanced mechanistic statements correctly validate the intricacies of transfo — Haloalkanes 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)?
💡 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.