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Question

Propose product with a appropriate stereochemistry in the following SN2 reaction.

A
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B
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C
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D
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Solution

The correct option is D
In SN2 reaction, the nucleophile attacks from the back side and forms a transition state and then the leaving group leaves. It is a single step concerted reaction. Thus, the rate of the reaction depends on both reactant and the nucleophile.

SN2 reaction gives inversion of configuration at α carbon. If the compound also has chiral carbon other than α carbon, configuration at those chiral carbons remains unchanged after the reaction.
In (a) and (c), the absolute configuration at alpha position is not changed.
In (b), the nucleophile get attached to beta carbon so it is not a correct product.
Thus, (d) is the correct answer.

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