Chapter 12, Problem 12.6YT

Interpretation Introduction

Interpretation:

The mechanism for the reaction in Equation 12-17 is as follows, but the curved arrows have been omitted. The mechanism by drawing in the curved arrows is to be completed. Also, the name of each elementary step below the appropriate reaction arrow is to be written.

Concept introduction:

A chlorohydrin is produced when an alkene is treated with ${\text{Cl}}_{\text{2}}$ in water. In the formation of a halohydrin from an alkene, the $\text{OH}$ group and the halogen atom add anti to each other. Step 1 is electrophilic addition that produces the chloronium ion intermediate, and Step 2 is an ${\text{S}}_{\text{N}}\text{2}$ reaction that produces a racemic mixture of enantiomers. The enantiomers are produced from the attack of the two different $\text{C}$ atoms bonded to the $\text{Cl}$ leaving group, but this example shows just the right side $\text{C}$ being attacked. In this example, ${\text{H}}_{\text{2}}\text{O}$ is the solvent and is present in a much larger concentration than ${\text{Cl}}^{-}$ and, therefore, wins out over ${\text{Cl}}^{-}$ as the nucleophile.