Chapter 12.3, Problem 6P

Interpretation Introduction

Interpretation:

The tertiary halides cannot be used in coupling reactions with Gilman reagents and the reason should be explained.

Concept Introduction:

Gillman reagent: The lithium copper (Diorganocopper) reagent compound $(R_{2}CuLi)$, these reagent are very useful because unlike Grignard reagent and organolithium reagents, they react with organic halides to replace the halide group with an alkyl (R) group.

Organometallic reagents such as organocuprates $(R_{2}CuLi)$ have a transition as their metal atom, they are used to form new carbon-carbon bonds.

• Organocuprate $(R_{2}CuLi)$ are also known as Gilman Reagent.
• It is prepared from an organolithium compound by reaction with cuprous iodide in diethyl ether or THF as follows.