Question

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

Short answer

In Suzuki reaction, aryl halide reacts with aryl boric acid in the presence of palladium catalyst and base, e.g., NaOH, to produce the aryl coupled product.

The product hexyl benzene is formed by coupling the phenyl ring with hexene; the hexene part comes from the reactant(Z)-1-bromohex-1-hex-1-ene (given), and thephenyl part is coming from phenylboronic acid in the presence of palladium catalyst and base, e.g., NaOH hexyl benzene is formed.

Phenylboronic acid reactant used to form the desired product

Step-by-step solution

Subpart (a) Predict the reactant to form hexyl benzene.

In Suzuki reaction, aryl halide reacts with aryl boric acid in the presence of palladium catalyst and base, e.g., NaOH, to produce the aryl coupled product.

The product hexyl benzene is formed by coupling the phenyl ring with hexene; the hexene part comes from the reactant(Z)-1-bromohex-1-hex-1-ene (given), and thephenyl part is coming from phenylboronic acid in the presence of palladium catalyst and base, e.g., NaOH hexyl benzene is formed.

Phenylboronic acid reactant used to form the desired product

Subpart (b) Predict the reactant to form hexyl benzene.

The product (E)-hepta-1,3-dien-2-ylbenzene is formed by coupling the vinyl benzene with pentene; the vinyl benzene part comes from the reactant(1-bromovinyl) benzene (given), and the pentene part is coming from(E) -pent-1enylboronic acid in the presence of palladium catalyst and base, e.g., NaOH is (E)-hepta-1,3-dien-2-ylbenzene formed.