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Coordination Isomerism

Optically act...

Question

Optically active $2$ -iodobutane on treatment with Nal in acetone gives a product which does not show optical activity. Explain briefly.

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Solution

$I^{-}$ is a good nucleophile as well as a good leaving group. Therefore, if $(R) - 2 - i o d o b u t a n e$ is treated with NaI, repeated $S_{N} 2$ reactions occur. As a result, eventually, a $racemic mixture of (\pm)-2 iodobutane$ is obtained which is optically inactive.

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