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Question

When a chiral [S]-alcohol is reacted with SOCl2 in presence of solvent like pyridine, chlorination happens, Predict the configuration and mechanism of product.

A
R, SNi
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B
S, SNi
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C
R, SN2
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D
R, SN1
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Solution

The correct option is C R, SN2
In SNi reaction, when a chiral alcohol is reacted with SOCl2, chlorination happens with retention of configuration. It takes place when no other solvent like pyridine is present.
But when external agent(base) is added, there is an inversion in the product because it then follows SN2 mechanism.


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