Experiement 15 Orgo 2.pdf - Nishant Menon Section 2924-002...

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Nishant Menon Section 2924-002 Dr. Jaskiran Kaur TA: Esha Kadakia Date Performed: 22 January 2020 Date Due: 29 January 2020 Experiment 15: The Diels-Alder Synthesis of 9,10-Dihydroanthracene-9,10-α,β-succinic Acid Anhydride from Anthracene and Maleic Anhydride Objective: The objective of this lab is to examine the reaction of a diene and dienophile with an aromatic ring. In this experiment, we will constitute the aromatic ring as the diene and maleic anhydride as the dienophile. In general, this reaction for this experiment follows a 1,4-addition by activated alkene dienophile across the 9,10 position of anthracene to form the product 9,10-dihydroanthracene-9,10- ɑ ,β-succinic acid anhydride. Lab techniques used in was crystallization through the use of a hirsch funnel. Experimental Procedure: The procedure was followed as described in Mayo, pages 271-273, with the modifications listed in the Canvas document. Additional modifications to the procedure included the following: 1. TLC procedure 2. Cold ether was used to wash the crystals instead of ethyl acetate 3. Recrystallization and chemical tests were not performed Reaction Scheme: Data and Results: Data Table One: Results from Experiment Anthracene Maleic Anhydride Xylene 9,10-dihydroanthracene-9, 10-α,β-succinic acid anhydride mol. formula C 14 H 10 C 4 H 2 O 3 C 8 H 10 C 18 H 12 O 3 amount (mg) 80 40 -- 110 81 amount (mL) -- -- 1.0 -- -- mmoles 0.45 0.41 8.1 0.41 0.29 molar mass 178.23 98.06 106.16 276.30 density 1.25 1.48 0.86 1.375 lit. bp (°C) 644 395.6 137-140 --
lit. mp (°C) 216 60 55.76 261-262 TLC: Elution in 80:20 hexane:ethyl acetate Anthracene Maleic Anhydride Xylene Product Distance traveled (cm) 6.4 6.4 6.4 6.4 Spot Distance (cm) 5.0 1.0 2.5 2.0 Rf 0.78 0.16 0.39 0.31 IR Spectrum: Calculations: 1. Theoretical yield of 9,10-dihydroanthracene-9,10- α,β -succinic acid anhydride.

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