Alkene Reactions: Diels-Alder Reaction

The Diels-Alder reaction is a cycloaddition reaction between a conjugated diene and a dienophile, resulting in the formation of a six-membered ring. It is a pericyclic reaction, which means it proceeds through a concerted mechanism where bonds are formed and broken simultaneously, without the formation of intermediates.

Reaction:

If you are trying to replicate this reaction using OrgoSolver, the Reaction Solver tool can only accomodate 1 reactant at a time. So, you can either draw the diene or the dienophile and select the corresponding reagent to form the Diels-Alder product:

Diels-Alder with diene:

Diels-Alder with dienophile:

The reaction mechanism is depicted below:

Mechanism:

The reaction mechanism involves the interaction of the pi-electrons of the diene with the pi-bond of the dienophile. The diene must be in the s-cis conformation to participate in the reaction, which allows the two double bonds to interact effectively with the dienophile. The result is the formation of new sigma bonds, creating a cyclohexene derivative.

Key Points of the Mechanism:

Concerted Process:

The reaction occurs in a single step without intermediates.

Stereospecificity:

The reaction preserves the stereochemistry of the dienophile, meaning that the configuration of substituents in the dienophile influences the configuration in the product.

Endo Rule:

When the dienophile has substituents capable of forming secondary orbital interactions, the product tends to favor the endo configuration, where these substituents are oriented towards the newly formed pi-system.

Practice this reaction using our Reaction Solver!