Question

Organic Synthesis Tutorial: Diels-Alder Products

Answer 1

\({\bf{Overall~Mechanism:}}\)


requires a diene in the cis-conformation (higher substituted ends both facing the same side), as well as a dienophile (this can also be a triple bond but will be focusing on DB dienophiles)



adduct preferentially forms endo product due to orbital overlap

Answer 2

The diene will be more reactive with EDGs (raises the energy of the HOMO) and the dienophile will be more reactive with the presence of EWGs (loweres the energy of LUMO)

\({\bf{General~Procedure:}}\) in our experiment we used anthracene as the diene and maleic anhydride as the dienophile





The mixture was then heated to reflux and filtered to get a solid product. The product was then re-crystallized (can't really say what solvent was used since we were meant to do a solubility test in the lab) and analyzed via NMR.

Answer 3

\({\bf{Safety~Information:}}\)
> filtrate from the diels alder reaction step goes into halogenated organic waste
> solutions from solubility test also go into halogenated organic waste. after being rinsed w/ acetone, put remaining filtrate in halogenated waste
> filtrate from recrystallization goes into non-halogenated organic waste