Question

Devise a synthesis of each compound from cyclohexene and any required organic or inorganic reagents.

a.

b.

Short answer

Answer

a.

b.

Step-by-step solution

Cyclohexene

Numerous hydrocarbons are present, and one among them is cyclohexene. They are unstable species and get converted to peroxides when they come in contact with air and light.

Reactions of cyclohexene

Cyclohexene undergoes hydration to produce cyclohexanol. It combines with N-bromosuccinimide (NBS) to form 3-bromocyclohexene.

Synthesis of each compound from cyclohexene

a. The given compound can be synthesized using three steps. The first step is the allylic bromination of cyclohexene by NBS in the presence of sunlight to form 3-bromocyclohex-1-ene. The second step is the hydrolysis of 3-bromocyclohex-1-ene to form cyclo-hex-2-enol. The third step is the treatment of cyclohex-2-enol with dibromocarbene, which is formed by the reaction of $\mathrm{KOC}{\left({\mathrm{CH}}_3\right)}_3$ with CHBr₃ to form the product. The reaction can be given as:

Synthesis of compound a from cyclohexene

b. The first step is the allylic bromination of cyclohexene. The second step is the Gilman reaction using ${\left({\mathrm{C}}_6{\mathrm{H}}_5\right)}_2\mathrm{CuLi}$ reagent. The third step is the synthesis of nonhalogenated cyclopropane by the Simmons-Smith reaction. The reaction can be given as:

Synthesis of compound b from cyclohexene