Question

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

Short answer

The predicted product is

Step-by-step solution

Diels – Alder Reaction

Diels- Alder reaction is similar to Michael reactionas both are 1,4 – addition reaction in this cyclic reaction product is formed thus also known as cyclic addition or cycloaddition reaction.

The product formed in Diels – Alder reaction is called adduct, here the reaction takes place between a conjugated diene and alkene or substituted alkene.

Product formed in Diels – Alder Reaction

In Diels Alder's reaction, two molecules combine to form a new ring in a one-step, known as a concerted reaction. This reaction involves the concerted forming and breaking of bonds within a closed ring of interacting orbitals.

Benzyne (produced from chlorobenzene and NaOH, heated) act as the dienophile when reacted with cyclopentadiene acting as a diene Diels alder reaction occurs and forms the new ring as the final product in Diels Alder's reaction.