Question

Devise a synthesis of (E)-1-phenylhex-1-ene ( ${\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}\mathbf{CH}\mathbf{=}\mathbf{CHPh}$) using hydrocarbons having ≤ 6 C’s and a Suzuki reaction as one of the steps.

Short answer

Answer

Mechanism of (E)-1-phenylhex-1-ene synthesis

Step-by-step solution

Organic synthesis

Generally, the demands for natural products are higher than the amount produced by nature. Therefore, the compounds have to be synthesized from smaller available organic compounds.

Therefore, organic synthesis is the route for the conversion of available starting materials to complex target molecules through a series of synthetic steps.

Coupling reactions, oxidation, reduction are carried out under controlled reaction conditions to increase yield in organic synthesis.

Suzuki reaction

Synthesis of biaryl compounds from aryl halides in the presence of aryl boronic catalyst is called Suzuki coupling.

The reaction was carried out in the presence of a homogenous palladium catalyst at a high temperature in an organic solvent.

Now, developed Suzuki reactions can be done in an aqueous solution using a heterogeneous catalyst.

Synthesis of (E)-1-phenylhex-1-ene

Pentane nitrile is the starting material. It reacts with aryl boronic acid to form the intermediate, which reacts with bromobenzene to form (E)-1-phenylhex-1-ene.

Bromobenzene is synthesized from benzene by bromination reaction.

Mechanism of synthesis of (E)-1-phenylhex-1-ene