Darzen's process () is universally recognized as the premier laboratory method for synthesizing pure — Haloalkanes and Haloarenes Chemistry Question
Question
Darzen's process ($R-OH + SOCl_2 \rightarrow R-Cl + SO_2 + HCl$) is universally recognized as the premier laboratory method for synthesizing pure alkyl chlorides. Which of the following mechanistic and practical facts accurately validate this reaction?
💡 Solution & Explanation
A) True. The volatile byproducts make this the "best method" as no complex separation is required. B) True. The $S_Ni$ mechanism involves a four-membered cyclic transition state yielding retention. C) True. The reaction of the alcohol and $SOCl_2$ rapidly produces the $R-O-S(=O)-Cl$ (alkyl chlorosulphite) intermediate. D) False. Phenol does not undergo substitution with $SOCl_2$ because the $C-O$ bond is resonance-stabilized and the $sp^2$ carbon strongly resists nucleophilic attack.