The following compound can undergo two successive S_N2 reactions.What are the products of these reactions?

Question

Quizplus · Accepted Answer

The first reaction would be a substitution, in which the leaving group (Br) would be replaced by the nucleophile (OH). This results in an intermediate in which the tetrahedral carbon has a positive charge. In the second reaction, this intermediate would undergo another substitution, in which the leaving group (H2O) would be replaced by another nucleophile (Cl). This results in the formation of product D, which has both Cl and OH groups attached to the same carbon atom. The other products (I, II, III) are not formed through two successive S_N2 reactions.

The Following Compound Can Undergo Two Successive SN2 Reactions

The Following Compound Can Undergo Two Successive S_N2 Reactions