Chapter 26, Problem 26.18P

In addition to organic halides, alkyl tosylates ( $\text{R'OTs}$, Section 9.13) also react with organocuprates $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ to form coupling products $\text{R-R'}$. When $2^{\circ }$ alky l tosylates are used as starting materials $\left({\text{R}}_{\text{2}}\text{CHOTs}\right)$, inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$.

a. b.