Diels - Alder Tutorial


The Diels - Alder Reaction

The Diels - Alder reaction is named after Otto Diels and Kurt Alder. In 1950 they were awarded the Nobel Prize for their work on this reaction. The Diels - Alder reaction is a cycloaddtion reaction between a two conjugated double bonds (a diene) and a carbon carbon double bond or triple bond (dienophile). The reaction is very important because two new carbon-carbon bonds and a cyclohexene ring are formed in a single step. The recation mechanism is pericyclic or concerted. In other words, the reaction is a single step process with no intermediates.


Diels-Alder image

Below is an interactive model of a Diels-Aldert reaction between cyclopentadiene and maleic anyhydride. By selecting the atoms which form the new ring, you can better visualize how the reaction takes place. You may also rotate the molecule to get any perspective you like.
C = grey; H = cyan; O = red

 

Alignment for endo transition state

Endo transition state
new bonds forming

Endo product
with correct bond angles


Alignment for exo transition state

Exo transition state
new bonds forming

Exo product
with correct bond angles


 

 

 

Created: March 11, 1998, University of Miami
Last updated: February 11, 2025, Northern Kentucky University
© 1998 - KC Russell