Question

Devise a synthesis of each compound using a Heck reaction as one step. You may use benzene, ${\mathbf{CH}}_{\mathbf{2}}\mathbf{=}{\mathbf{CHCO}}_{\mathbf{2}}\mathbf{Et}$, organic alcohols having two carbons or fewer and any required inorganic reagents.

a.

b.

Short answer

Answer

a.

b.

Step-by-step solution

Heck reaction

The reaction between an unsaturated alkyl halide and an alkene in the presence of a palladium catalyst and a base yielding a substituted alkene is named the Heck reaction.

Example of a Heck reaction

Example of a Heck reaction

Synthesis of compound a

The reaction involves three steps:

• Synthesis of p-bromoanisole

Synthesis of p-bromoanisole

• Synthesis of p-bromoanisole

Synthesis of the aromatic alkene

• Heck reaction

Heck reaction yielding compound a

Synthesis of compound b

The reaction involves the following steps:

• Synthesis of 4-Bromo-2-ethylanisole

Synthesis of 4-Bromo-2-ethylanisole

• Heck reaction

Heck reaction yielding compound b