Question

What steps are needed to convert but-1-ene \((C{H_3}C{H_2}CH = C{H_2})\) to octane \((C{H_3}{(C{H_2})_6}C{H_3})\)using a coupling reaction with an organocuprate reagent? All carbon atoms in octane mustcome from but-1-ene.

Short answer

Coupling reactions can be of several types, and one among them is the organocuprate coupling reaction. These reactions are stereospecific if the organic halide is a vinyl halide.

Step-by-step solution

Coupling reactions

Coupling reactions can be of several types, and one among them is the organocuprate coupling reaction. These reactions are stereospecific if the organic halide is a vinyl halide.

Features of organocuprate coupling reactions

The product generated by combining an organic halide with an organocuprate reagent comprises a new C-C bond. Several organic halides, such as methyl alkyl halide and vinyl halides, can be employed for this reaction.

Step 3:Conversion of but-1-ene to octane using a coupling reaction

But-1-ene undergoes reaction with HBr and peroxide to form 1-bromobutane. The resultant product can react with Li and CuI to form the organocuprate reagent. This reagent can couple with but-1-ene to form octane. The reaction can be given as follows.

Conversion of but-1-ene to octane