Question

Diels-Alder Post-lab (1) - Compatibility Mode Layout References Mailings Review View Help Search Please write the answers to the following questions directly in your notebook. 1. Discussion of the Diels-Alder reaction performed, including the calculated percent yield and comments on purity based on the product literature melting point.

Answer 1

This reaction ia a example of Diels Alder reaction using reflux between anthracene and maleic anhydride to produce 9,10-dihydroanthraceno-9,10,-endo-α,β-succinic anhydride. In this reaction anthracene acts as the diene and maleic anhydride is the dienophile because it contains electron withdrawing ester groups. Reactants come together to produce a cyclic product with endo stereochemistry.

Mechanism:

concerted mechanism has been proposed

ว ) :o : anthracene maleic anhydride 9,10-dihydroanthrceno-9,10-endo-a.ß-succinic anhydride

Yield :

. . 98.06 g/mol noof moles of authlanene al sug = 10.32 mmol 178.23 g/mol no of moles of mebel Cantryside = 1:06 r = 10.81 mmol anthracene is limiting reagent here hence completly consamed no of moles of product = 10:32 mmol expeted mass = 10:32 mol x 278.319 1 mol 70-3 = 2.879. Actual mass obtained =2.05g - actual actual mass x 100 eact = expected mass = 2.05 2.87 X 100 x 100 = 71.35% 6 Il melting point is lowered than it - suggest that there is some empunity or es sample utt.. some of reactant/s -