The Diels-Alder Reaction Anthracene with Maleic Anhydride

Abstract:

A Diels-Alder reaction was performed between anthracene and maleic anhydride to form 9,10-dihydroanthracene-9,10- -α, β-succinic anhydride. The Diels-Alder reaction involves using a diene (anthracene) and a dienophile (maleic anhydride). The yield of the crude product from this experiment could not be determined since it was not massed when it was collected. However, IR analysis using the Nicolet IR 100 was performed. Melting point determination of the crude product was 260-270 C. After collecting the crude product recrystalization was performed using xylene and vacuum filtration at which time the melting point of purified product was determined to be 262-266 C. Comparison to literature melting points of 262-264 C indicated that the product was 9,10-dihydroanthracene-9,10- -α, β-succinic anhydride and was more pure than the crude product. The IR spectrum analysis graph was shown to have similarities with the IR spectrums of both anthracene and maleic anhydride indicating that the product was a combination of both confirming a successful experiment.

Introduction:

The Diels-Alder reaction is an important chemical reaction which won the Nobel Prize in Chemistry in 1950 for Otto Diels and Kurt Alder. The purpose of this experiment is to use the Diels-Alder reaction between the reactants anthracene and maleic anhydride to form 9, 10-dihydroanthracene-9,10-α, β-succinic anhydride. The Diels-Alder reaction is a [4+2]-cycloaddition reaction using the 4 pi electrons of a diene and 2 pi electrons of a dienophile to give a polycyclic Diels-Alder product. It uses the 1,3- diene anthracene and the dienophile is maleic anhydride. The Diels-Alder reaction is favored by electron withdrawing groups on the dienophile and electron donating groups on the diene. There are 3 double bonds in the reactants that are converted into two new single bonds and one new double bond during the reaction. The double bond of the dienophile adds to the diene to give a product...