The Diels-Alder Reaction Of Anthracene With Maleic AnhydrideEssay Preview: The Diels-Alder Reaction Of Anthracene With Maleic AnhydrideReport this essayThe Diels-Alder Reaction of Anthracene with Maleic Anhydride 1 The Diels-Alder Reaction of Anthracene with Maleic AnhydrideMicroscale Diels-Alder ReactionLeah MonroeMarch 6, 2003Organic Chemistry Lab IIExperiment performed on February 25 and 27, 2003Abstract:This experiment involved a reaction between anthracene and maleic anhydride via a Diels Alder reaction to yield 9, 10-dihydroanthracene-9,10-α, β-succinic anhydride. Anthracene was the diene and maleic anhydride was the dienophile. The percent yield of the crude product was 69.03%. Following recrystallization of the product using xylene and vacuum filtration, a percent yield of 37.42% for the recrystallized product was collected. This was low due to the fact that some of the crude product was not recrystallized and was instead used to take a melting point of the crude product. It was also low due to several of the crystals being stuck inside the flask and not going into the funnel. The percent recovery from recrystallization was 54.21%. The melting point of the crude product was 261 – 264oC. The melting point of the recrystallized product was 261 – 263oC. Comparing these values with the literature melting point of 262 – 264oC shows that the product was indeed 9, 10-dihydroanthracene-9, 10-α, β-succinic anhydride and that recrystallization yielded a purer product. Upon examination of an infrared spectrum of the product and comparison with anthracene and maleic anhydride spectra, it was found that the product spectrum had similarities with both the anthracene spectrum and the maleic anhydride spectrum. This indicated that the product was an adduct of both anthracene and maleic anhydride, and thus that the experiment was successful.
The Diels-Alder Reaction of Anthracene with Maleic Anhydride 2Introduction: The purpose of this experiment is to form 9, 10-dihydroanthracene-9,10-α, β-succinic anhydride by way of a Diels Alder reaction between anthracene and maleic anhydride. Anthracene acts as the diene and maleic anhydride functions as the dienophile. Following the reaction, the crude product will be recrystallized. Melting points of both the crude product and recrystallized product will be taken and compared with the literature value. Also, an infrared spectrum of the recrystallized product will be taken. Both melting points and the infrared spectrum will be used to characterize the product.
Materials Used:150-mL beaker Hirsch funnel, with adapterboiling chip 2 melting point capillary tubesCondenser, with tubing Pasteur pipet, with latex bulb5-mL conical vial microspatula2 Erlenmeyer flasks, 10-mL 1-mL pipet25-mL filter flask, with vacuum tubing sand bathfilter paper support standglass stirring rod 13 x 100-mm test tubethermometer, -10 to 260oCSubstancesFormula Weightg/molQuantityMoles UsedMole RatioMelting PointBoiling Pointanthracene178.23100 mg5.611 x 10-41 to 1216 – 218N/A9,10-dihydroanthracene-9, 10-α, β-succinic anhydride276.29product1 to 1262 – 264N/Amaleic anhydride98.0655 mg5.609 x 10-41 to 154 – 56N/Apotassium bromide119.01100 mg8.4 x 20-4N/Axylene106.176 mL137 – 144Reagents and Properties:Reaction and its Mechanism:Overall Reaction: C14H10 + C4H2O3 C18H12O3C O C O O + Anthracene (diene) Maleic anhydride (dienophile) C O H H C O O 9,10-dihydroanthracene-9,10-α, β-succinic anhydrideMaleic anhydride (dienophile) C O O C O C O H H C O O Anthracene (diene) 9,10-dihydroanthracene-9,10-α, β-succinic anhydrideThe Diels-Alder Reaction of Anthracene with Maleic Anhydride 3Procedure:Part 1 – Reacting Anthracene with Maleic AnhydrideTare a 5-mL conical vial (or 10x 100-mm reaction tube) and record the mass. Weigh 100 mg of anthracene and 55 mg maleic anhydride and place them in the vial or reaction tube. Add 1.0 mL of xylene and a boiling chip. Fit the vial or tube with a condenser, as shown in Figure 3 on page 79 of Chemistry Lab Experiments. Turn on the water to the condenser or add a wet pipe cleaner around the reaction tube. Use a 200oC sand bath to heat the mixture at reflux for 30 minutes, boiling vigorously to ensure good mixing. Cool the mixture to room temperature and prepare an ice bath using a 150-mL beaker. Then cool the mixture in the ice bath for approximately 5 minutes. At the same time, pour 2 mL xylene into a test tube and chill the xylene in the ice bath. Collect the recrystallized solid by vacuum filtration using a Hirsch funnel and rinse the crystals with 1 mL of ice-cold xylene. Weigh the crude product and set aside a small sample to dry. This sample will later be used to measure the melting point of the crude product.
Part 2 – Purifying the ProductTo perform recrystallization, place the product in a 10-mL Erlenmeyer flask. Add 1 – 2 mL of xylene and heat the mixture gently in a sand bath until the xylene boils. Gradually add more xylene until all the product dissolves or until no more appears to be dissolving. Be sure not to exceed 3 mL of total volume xylene. If solid impurities are still present, use a Pasteur pipet to transfer the solution to another 10-mL Erlenmeyer flask. Allow the solution to cool to room temperature and then cool the solution in an ice bath for 5 minutes. If its necessary, scratch the bottom of the flask with a glass rod to induce crystallization. Collect the crystallized solid by
dissolve
into 3 mL of xylene, and add to the boiling point of the xylene. Refrigerate overnight. The liquid should have accumulated in less than a quarter of an hour until needed. Then use a Pyrex Lysis™ (one-in-1 L/7oz x 1 gallon) filter and add 1 L of xylene to the mixture in the Filter. Continue chilling the filtered liquid in a glass container until you are ready to perform the decroting. Cool down the lids using an airtight (45-degree) lid and stir often in a small bowl until they are soft and the liquid has been filtered out. If the Lids are too warm, the liquid may come to rest in the bottom of the bowl. When removing the filter, take off the cap and pull the filter back out. Remove the top plate with the filters and let cool.
Part 2 — Purifying the ProductTo perform recrystallization, remove the product from a container of 50 gallons. Remove the top plate and remove the top liner from a plastic bag placed next to the filter in case of an open container. Once fully removed, place the top liner over the filter cover and add 1 L of xylene, the rest of the contents covered with the lid. Return the container to the container and stir often until the top liner is thoroughly removed from the filter cover and the top liner comes to rest easily in the plastic bag. Remove the lid and return it to the container. Place the Filter on top of the filter cover and stir frequently until thoroughly dry. Remove its remaining lid, and repeat with the lid after each use.
Lid 1 ― Purifying the ProductTo perform recrystallization, remove the product from a 60 gallon glass bottle. Attach the lid to the top of the glass bottle when it is in a 5 gallon jug. Pour a bit of the xylene into the bottom of the box at the same time and continue stirring until the bottom of the glass bottle contains 1L xylene (5mL x 5oz x 1 gallon). Return the lid to the top of the bottle, and repeat with the contents of the water. Using tongs, remove your glass from the bottoms with the lid still attached (if one is already securely attached). If it is not already fully submerged, use a separate tong and drain it (if there are no other bottle holders).
Lid 2 ‖ Purifying the ProductTo accomplish recrystallization, submerge the lid in a 3/4 lb. (3.2 lb. in. T-bott