Chapter 17, Problem 17.65P

Interpretation Introduction

Interpretation:

The reagents necessary to perform the given transformation are to be provided.

Concept introduction:

The organometallic compounds such as Grignard reagents (RMgX) and alkyllithium reagents behave both as strong bases and as strong nucleophiles. Both alkyllithium reagents and Grignard reagents can react rapidly with water in a substantially exothermic proton transfer reaction to produce an alkane and ${\text{HO}}^{\text{-}}$. When R-Li or R-MgX reacts with a compound containing a polar $\text{π}$ bond, ${\text{R}}^{\text{-}}$ acts as a nucleophile and adds to the electron-poor atom of the polar $\text{π}$ bond. Once this is complete, aqueous acid (${\text{H}}_{\text{3}}{\text{O}}^{+}$) is added in an acid workup to protonate the strongly basic ${\text{O}}^{\text{-}}$ generated in the first step. Strong bases tend to favor E1 reactions. The E1 reaction products are obtained by eliminating the leaving group and a proton on a carbon adjacent to the one bonded to the leaving group.