Lab Report- Exp 1 Diels Alder Reaction

Lab Report- Exp 1 Diels Alder Reaction - Lauren Barton...

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Lauren Barton Experiment 1: Diels-Alder Reaction Dr. Kwan Organic Chemistry Lab II CH 224-54 THURS PM
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Introduction: In this lab, a Diels-Alder reaction formed a six-membered ring of cyclohex-4-ene-1,2- dicarboxylic anhydride when a conjugated diene, Butadiene sulfone, was reacted with a dienophile, Maleic Anhydride. The six membered ring was formed through a concerted mechanism in which the s-cis conjugated diene with a 4pi electron system and a dienophile with a 2pi electron system’s pi orbitals overlapped and preformed [4+2] cycloaddition under heat. 1 The conjugated diene, butadiene sulfone was refluxed in order to produce 1,3-butadiene as seen in Figure 1 below . The solid butadiene sulfone was used initially instead of 1,3-butadiene gas because it is more stable at room temperature and is easier to handle, weigh, and measure to determine the exact amount used. 1 The addition mechanism of butadiene sulfone and maleic anhydride to form the product, 4-cyclohexene-cis-1,2-dicarboxylic anhydride, through a Diels- Alder reaction can be seen in Figure 2. The product formed underwent recrystallization and was put through vacuum filtration yielding white crystals. The purity of the product was determined by quantity and quality of the crystals formed through appearance, percent yield, IR spectrometry, and melting point. The structures of butadiene sulfone, 1,3-butadiene, maleic anhydride, and 4-cyclohexene-cis-1,2-dicarboxylic anhydride can be seen in Table 1 below. Figure 1 : Butadiene sulfone refluxed to 1,3-butadiene then added to Maleic Anhydride 1 S O O Heat + O O O Heat O O O H H 1,3-butadiene Figure 2: Mechanism of Formation of 4-cyclohexene-cis-1,2-dicarboxylic anhydride 1 S O O + O O O maleic anhydride Butadiene sulfone Heat O O O H H O O O H H
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Table 1: Physical Data of Experimental Components 2,3 Compound Melting Point o C Boiling Point o C Weight (g/mol) Structure Butadiene Sulfone C 4 H 6 O 2 S 65-66 o C decomposes 118.15 g/mol Maleic Anhydride C 4 H 2 O 3 51-56 o C 200 o C 98.06 g/mol 1,3-Butadiene -109 o C -4.5 o C 54.09 g/mol Cyclohex-4-ene- 1,2-dicarboxylic Anhydride C 8 H 8 O 3 97- 103 o C 152.15 g/mol NaOH 318 o C 1,388 o C 39.99 g/mol Na-OH Petroleum Ether 30-50 o C Xylene C 6 H 4 (CH 3 ) 2 137-140 o C Toluene C 6 H 5 CH 3 -93 o C 110-111 o C 92.14 g/mol Experiment:
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To begin the experiment, a sand bath was set up on a hot plate and a thermometer was added and held upright by a clamp. The hot plate was set on high, and once the temperature reached 190 o C it was maintained between 150-200 o C. Approximately 0.207 grams of butadiene sulfone was measured and placed into a 4.0mL conical vial. Next, 0.095 grams of maleic anhydride was measured and placed inside the same 4.0mL conical vial. A 1 mL pipet was then
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Lab Report- Exp 1 Diels Alder Reaction - Lauren Barton...

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