devarshi-dt-logo

Question:

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

(±)𕒶−iodobutane

(±)𕒵,2−diiodobutane

(R)𕒶−iodobutane

(S)𕒶−iodobutane

Solution:

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.