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Question

(R)-2 -Iodobutane is treated with NaI in acetone and allowed to stand for a long time.The product eventually formed is:

A
(R)2iodobutane
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B
(S)2iodobutane
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C
(±)2iodobutane
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D
(±)1,2diiodobutane
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Solution

The correct option is C (±)2iodobutane
I is a good nucleophile as well as a good leaving group. Therefore, if (R)-2-iodobutane is treated with NaI, repeated SN2 reactions occur. As a result , eventually a racemic mixture of (±)-2 iodobutane is obtained.
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