Question

When a chiral alcohol is reacted with $SOC{l}_2$, chlorination happens with retention of configuration, when no other solvent like pyridine is present. which mechanism is followed by this reaction?

• A. $S_{N}1$ mechanism
• B. $S_{N}2$ mechanism
• C. $S_{N}i$ mechanism
• D. E1 mechanism

Answer 1

The correct option is C $S_{N}i$ mechanism

$S_{N}i$ stands for Substitution Nucleophilic Intermolecular.
In this reaction when a chiral alcohol is reacted with $SOC{l}_2$, chlorination happens with retention of configuration, when no other solvent like pyridine is present.
But when external agents are added (nucleophilic solvent like pyridine ) there is a inversion in the product.