Question

Synthesize each product from the given starting materials using an organocuprate coupling reaction.

Short answer

Answer

a.

b.

c.

Step-by-step solution

Organocuprate coupling reaction

An organic reaction involves the formation of a new carbon-carbon bond by coupling two moles of an alkyl halide with an organocuprate reagent$\left(R_2\mathrm{CuLi}\right)$ .

Synthesising compounds

The given compounds are synthesized as follows:

a. The bromobenzene is treated with lithium and cupric iodide to form the corresponding lithium diphenyl cuprate. This is allowed to react with organo iodide to form the required

compound.

Organocuprate coupling reaction to form substituted benzene

b.Butyl chloride reacts with lithium, followed by cupric iodide to form the lithium dibutyl cuprate that reacts with bromobutene to form the required hydrocarbon.

Organocuprate synthesis of Oct-3-ene.

c. 1-Chloro-3-methyl propane reacts with lithium, followed by cupric iodide to form lithium 3-methyl propane cuprate that reacts with another molecule of 1-chloro-3-methyl propane to form the required hydrocarbon.

Organocuprate synthesis of 3,8-dimethyldecane.