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Question

Predict the configuration of A and B at chiral carbon.

A
A- R; B-S
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B
A- S; B-R
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C
A- R; B-R
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D
A- S; B-S
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Solution

The correct option is A A- R; B-S
SNi stands for Substitution Nucleophilic Intermolecular.
In this reaction when a chiral alcohol is reacted with SOCl2, chlorination happens internally with retention of configuration.

But, when external agents are added (nucleophilic solvent like pyridine ) there is a inversion in the product because here the Cl attacks the chiral carbon from the back externally as a SN2 mechanism.

By CIP rule, configuration of substrate is 'R'
Hence, configuration of A and B are R and S respectively.


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