Diels Alder Reaction

The Diels-Alder reaction is a Pericyclic reaction. Pericyclic reactions are concert (i.e all bond breaking and making in a single step) and proceeds through a cyclic aromatic transition state. It is the reaction of a diene and a dienophile and is reffered to as a (4π + 2π) cycloaddition reaction since 4π electrons are involved in the diene and 2π in the dienopihile, but there are other types (e.g. (6π + 2π))

Lab Lore

Robert Burns Woodward, regarded as the greatest organic synthesis chemist of the 20th century, conquered natural products from quinine to vitamin B₁₂. His monumental B₁₂ synthesis with Albert Eschenmoser led directly to the Woodward–Hoffmann rules for conservation of orbital symmetry in pericyclic reactions like the Diels–Alder.

Drawing Diels-Alder Products

1) Draw a dotted line from ends of diene to the ends of the dienophile.

2) Shuffle electrons around and draw the product.

Reactants Next Prev Product

Animation

On Off