orgo_lab_1_spring - 1 Joy Gonzalez Performed 1/22 Chem...

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1 Joy Gonzalez Performed 1/22 Chem 2204 Due 1/29 TA: Experiment 15: Diels-Alder Reaction of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride Objective: Observing a diels-alder reaction and exploring the role of an aromatic ring system as the diene substrate in the reaction. Procedure and Modifications: The procedure is the same as experiment 15 in Mayo’s microscale organic lab manual, pages 269-273, except for the following modifications: The crude product will not be crystallized Omit the chemical tests step Substitute drierite for calcium chloride in the drying tube Reaction Scheme:
2 Data and Results: Name Formula Molar mass (g/mol) Amount mmol Equiv Mp Bp Anthracene C 14 H 10 178 92.0 mg .516 1.1 216 C 340 C Maleic anhydride C 4 H 2 O 3 98.1 42.0 mg .428 1 53 C 202 C Xylenes C 8 H 10 101 1.00 ml 8.60 n/a ranges 140 C 9,10- dihydroanthr acene-9,10- α,β-succinic acid anhydride C18H12O3 276 118 mg (TY) 41.0 mg (EY) .427 (TY) .148 (EY) 1 52 C 261-262 C (lit) 255.5 C (measured) Observations: Sand bath temp ~165 C, thermometer was broken and had gaps in mercury.

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