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Question
Explain the mechanism of SN1 reaction by highlighting the stereochemistry behind it.
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Solution
In SN1 reactions, if the alkyl halide is optically active, the product obtained in a racemic mixture. The intermolecular carbocation formed in slowest step being sp2 hybridized is planar species. Therefore the attack of the nucleophile OH on it, can occur from both the faces with equal case forming a mixture of two enantiomers. Thus SN1 reaction of optically active alkyl halides is accompanied by racemization.
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