Lab Report- Exp 1 Diels Alder Reaction

Because the vial only sat on ice for 10 minutes the

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Unformatted text preview: the solution might not have completely recrystallized. If the vial was left on ice for a longer amount of time, more crystals would’ve formed. A third area of product loss occurred when pouring the crystals and solution onto the filter paper in the vacuum filter. Not all of the crystals escaped the vial when it was emptied, even when rinsing it with 1 mL of petroleum ether, which reduced the yield. Another area of product loss occurred when emptying the crystals from the filter paper to an aluminum tray. Not all of the crystals were removed from the filter paper because they were stuck to the paper’s surface. As much product as possible was scraped from the paper and onto the tray but because the crystals were so small, not much product was obtained after all of the product loss that occurred throughout the experiment. The IR spectrometer was not working for our class therefore could not be used to determine the purity of my specific product. The IR graph on Blackboard however shows a pure sample of 4-cyclohexene-cis-1,2-carboxylic anhydride which is composed of a cyclohexene and two carbonyl groups. The C=C group peaks on the graph at 3116.4 and the two C=O groups, electron withdrawing groups, peak on the graph at 1770.3. The peaks on the Blackboard IR graph are what our products should’ve looked like if they were pure and the IR spectrometer was working. Diels-Alder Reaction Pre Lab: 2. It is important to avoid water in these reactions because in the presence of water both maleic anhydride and butadiene sulfone are hydrolyzed. Maleic anhydride will react with water to form maleic acid, which will not allow recrystallization of the product; the reaction scheme is shown below in Figure 4. Figure 4: Hydrolysis of Maleic Anhydride5 Wh en a cyclic a n h yd r id e, s u ch a s m a leic a n h yd r id e, is t h e d ien op h ile in a Diels ­Ald er r ea ct ion , t h e p r od u ct is a ls o a n a n h yd r id e. H yd rolys is of t h e a n h yd r id e oft en follows a s t h e n ext r ea ct ion in a s yn t h et ic s equ en ce. In s t ea d of h yd r oly...
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This document was uploaded on 04/06/2014.

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