Diels-Alder Cycloaddition Using Cyclopentadiene
A Diels-Alder reaction is between a conjugated diene and a substituted alkene called a
dienophile. The product of this reaction gives substituted cyclohexane giving a standard example
of a pericycle reaction. In the dicyclopentadiene was cracked using heat to form two molecules
of cyclopentadiene. This was able to happen using retro Diels-Alder reaction and then keeping
the products heating to stop cyclopentadiene from reacting with itself via Diels-Alder. The
cyclopentadiene was then added to another solution creating an anhydride product. later this
product was heated in water and then cooled to obtain a final product that had a melting point of
180-183 degrees Celsius. The process took about three hours and the final product dried for a
week before the melting point was obtained.
Upon entering the lab, a fractional distillation apparatus was set up containing
dicyclopentadiene. The dicyclopentadiene was heated between 40-43 degrees Celsius and ran
through the apparatus until three mL of cyclopentadiene was collected. For dicyclopentadiene to
crack into cyclopentadiene a retro Diels-Alder reaction had to occur. The following process
shows how this is done using heat. The reverse reaction is cyclopentadiene reacting with itself to
form back into dicyclopentadiene. In that Diels-Alder reaction cyclopentadiene is acting as both
the diene and dienophile.
The cyclopentadiene will react with itself via a Diels-Alder reaction if not kept warm so the
cyclopentadiene stayed on heat until it was ready to mix into the next solution. The next solution
was made up of maleic anhydride, ethyl acetate, and hexanes. One mL of cyclopentadiene was
then added to the solution once it had cooled. With cyclopentadiene added an exothermic
reaction happened allowing a product to form. The product was then dissolved using heat and
cooled again to create the anhydride product. This product was vacuum filtered before used in
the second half of lab. Once dried it was weighed and then added to water to be dissolved. The
solution was then allowed to cool until all solid had precipitate. Product was vacuum filtered and
then left to dry for a week. The following week a melting point was obtained for the product. The
melting point was 180-183 degrees Celsius. An NMR and IR analysis were obtained as well.
The overall reaction provided an eighty percent yield. A lower percent yield was obtained
because after the first crystallization some of the product was stuck to the inside of the flask and
this happened again with the diacid product as well. The melting point of the product was
between 180-183 degrees Celsius which matched very closely to the lit value of the diacid
product. This means the experiment was done with little error allowing the product to be pure.
The IR data has peaks showing the carbonyl groups and the NMR data has three peaks all close
to two giving the ability to see the chemical shift and integration of the peaks. Combined this
data gives the ability to see how well the experiment showing error or little error. Combined with
the melting point it shows the diacid product was pure and had no impurities. There was a low
percent yield but that was mainly done to crystallized products getting stuck in flasks.
