Thursday, February 6, 2020

If SOCl2 reacts with alcohols via SNi, why doesn't POCl3?

The reaction with SOClX2 is also used instead of PClX3 and PClX5 when retention of stereochemistry is required. Phosphorus trichloride and phosphorus pentachloride both lead to inversion.
SNi mechanism with thionyl chloride. (Chemsketch)


The mechanism proceeds via a SNi pathway, or internal nucleophilic substitution. This step has been highlighed in red; an intimate ion pair[see below] is given in square brackets. Adding a nucleophilic solvent such as pyridine considerably increases inversion with SOClX2 via an attack at the sulfur atom. Green marks blocking of the intramolecular substitution; blue is for inversion.

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आज नहीं तो कल होगा

हर एक संकट का हल होगा, वो आज नहीं तो कल होगा माना कि है अंधेरा बहुत और चारों ओर नाकामी माना कि थक के टूट रहे और सफर अभी  दुरगामी है जीवन ...