When a chiral alcohol is reacted with $S O C l_{2}$ , chlorination happens with retention of configuration, when no other solvent like pyridine is present. which mechanism is followed by this reaction?

E1 mechanism

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S_{N} i

mechanism

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S_{N} 2

mechanism

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S_{N} 1

mechanism

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Solution

The correct option is B $S_{N} i$ mechanism
$S_{N} i$ stands for Substitution Nucleophilic Internal.
In this reaction when a chiral alcohol is reacted with $S O C l_{2}$ , 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.

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S O C l_{2}

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