Expt 15_ Diels-Alder Reaction_ 9,10- Dihydroanthracene-9,10-α,β-succinic Acid Anhydride.docx

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Expt 15: Diels-Alder Reaction: 9,10- Dihydroanthracene-9,10-α,β-succinic Acid Anhydride Objective: The purpose of this experiment is to understand the role of an aromatic ring system as a diene substrate in the [4+2] cycloaddition reaction (Diels-Alder). In this experiment, anthracene is the diene and maleic anhydride is the dienophile, which will undergo a 1,4 addition by the activated dienophile across the 9,10 position of anthracene. Experimental Procedure: Experiment 15 was followed as described in Mayo, pg 271-272, with modification listed on Blackboard document. Reaction Scheme: Data and Results: Compound M.F Mol. Weight (g/mol) Amount mmol mp( ) bp( ) Anthracene C14H10 178.24 830mg 4.66 216 Maleic Anhydride C4H2O3 98.06 450mg 4.59 60 Xylene C8H10 106.16 1.0ml 137-140 Ethyl Acetate C4H8O2 88.11 300µ 77 9,10- Dihydroanthracene- 9,10-α,β-succinic Acid Anhydride C18H12O 3 276 45mg 0.165 261-262
Observation: Solution turned yellow after adding xylene Solution turned greenish-yellow during heating up 170 -180 started bubbling Greenish-yellow slowly disappeared

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