The Diels-Alder Reactionof Anthracene withMaleic Anhydrideprepared by L. G. Wade, Jr., Whitman College. Use the Diels-Alder reaction to form a bridged polycyclic anhydride.Recrystallize the product and characterize it by using melting point andinfrared spectroscopy. The Diels-Alder Reaction of Anthracene with Maleic Anhydride 2 Introduction: 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.
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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…show more content… Maleic anhydride and the product of the reaction are severe skin irritants. Be sure to wear gloves and avoid contact with these compounds.
2019-11-21 Other names: Anthracene, 2,5-furandione adduct; Anthracene,maleic anhydride adduct; endo-9,10-(α,β-Succinic anhydride)anthracene; 9,10(3',4')-Furanoanthracene-12,14-dione; 9,10-Dihydroanthraceno-9,10-endo-α,β-succinic anhydride; 9,10-Ethanoanthracene-11,12-dicarboxylic anhydride … Jump to content. anthracene 9, 10-dihydroanthracene- 9,10-oçß-succinic anhydride* maleic anhydride potassium bromide xylene *product 1998 Chemical Education Resources 10-mL graduated cylinder hot plate 2 melting point capillary tubes microspatula 25-mL round-bottom flask support stand 13 x 100-mm test tube 2 utility clamps 3-mL product vial watch glass Diels Alder Rxn - SEE TITLE SEE TITLE .
Weigh out 0.80g of anthracene and 0.40g of maleic anhydride (both are solids). Add the two solids into the flask. (Be sure the flask has cooled for at least two minutes before adding the solids, or they will melt.) Carry the round-bottomed flask to the hood This lab experiment was successful because we were able to identify that the anthracene was the diene and maleic anhydride was the dienophile.
InChI. InChI=1S/C18H12O3/c19-17-15-13-9-5-1-2-6-10 (9)14 (16 (15)18 (20)21-17)12-8-4-3-7-11 (12)13/h1-8,13-16H. InChI Key. NG NAME nc The Diels-Alder Reaction; Synthesis of 9,10-Dihydroanthracene-9,10-endo-a, B-succinic Anhydride Anthracene, an aromatic hydrocarbon, functions as a diene while reacting with maleic anhydride (a dienophile) to yield an "endo" Diels-Alder adduct, according to the chemical equation below 0 10 Anthracene (Diene) Maleic Anhydride (Dienophile) Diels-Alder Adduct Pre-lab Exercises 1. Maleic anhydride is a classic substrate for Diels-Alder reactions. Anthracene acts as the diene and maleic anhydride functions as the dienophile. The Diels-Alder anhydride produced was then hydrolyzed to produce the carboxylic acid. Anthracene-maleic anhydride diels-alder adduct.
Assume you start with 1.012 gram anthracene and 0.505 grams maleic anhydride: what is the theoretical yield of the product? 1.012 grams Anthracene 1 mole anthracene 1 mole product 276.29 grams 1.56879 178.23 grams 1mole anthracene 1 mole product LIMITING REAGENT 0.505 grams maleic anh. 1 mole maleic anh. 1 mole product 276.29 grams 1.422868
The reaction for this experiment is between anthracene and maleic anhydride and is a Diels-Alder reaction. This reaction is a cycloaddition reaction in which the conjugated pi-systems of the two reactants join to form a new ring 1. The pi-system in this case is referring to a carbon-carbon double bond within the ring.
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Experimental. To start the experiment, 0.289 g of anthracene and 0.16 g of maleic anhydride were put into a 5 mL round bottom flask. Then, 3 mL of xylene was added to the mixture and stirred. Balanced Chemical Equation for reaction of maleic anhydride + anthracene in xylene. INCLUDE NAME, STRUCURAL & CONDENSED FORMULA, AND MM. LABEL DIENE AND DENOPHILE. The reaction studied in this experiment is an example of a 1, 4 addition by an activated alkene dienophile across the 9, 10 positions of anthracene. This lab experiment was successful because we were able to identify that the anthracene was the diene and maleic anhydride was the dienophile.
when maleic anhydride reacts with anthracene, it adds to the. By - February 27, 2021. 0. 1. Share on Facebook. Tweet on Twitter
Anthracene-maleic anhydride diels-alder adduct | C18H12O3 | CID 138503 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. Anthracene with Maleic Anhydride The Diels-Alder reaction is a member of a class of reactions called cycloadditions.
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While the product is not an insecticide and does not Figure 2. Reaction to form cis -Norbornene-5,6-endo -dicarboxylic anhydride (Pavia 417). (2) Write the potential Diels-Alder reactions of maleic anhydride and anthracene, and (3) estimate the reaction enthalpy changes for these and for the analogous Abstract. The first page of this article is displayed as the abstract. The influence of light on the Diels-Alder reaction between anthracene and maleic anhydride. You The standard molar enthalpy of combustion of the (anthracene + maleic anhydride) adduct at po = 0.1 MPa was determined to be ΔcHmo(C18H12O3, cr, 298.15 K) This experiment involved a reaction between anthracene and maleic anhydride via a Diels Alder reaction to yield.
It was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950. It is through this reaction that maleic anhydride converted to many pesticides and pharmaceuticals.
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1-octylmaleimide or maleic anhydride as a dienophile, assisted by their crystal structures could serve as a reference for such an endeavor. An octylmaleimide Diels–Alder adducts of anthracene (1) and a 9-substituted derivative (2) were obtained by reacting the corre-sponding anthracene derivative with 1-octylmaleimide as de-scribed in Scheme 1. Anthracene-maleic anhydride diels-alder adduct contains total 37 bond(s); 25 non-H bond(s), 14 multiple bond(s), 2 double bond(s), 12 aromatic bond(s), 1 five-membered ring(s), 5 six-membered ring(s), 2 nine-membered ring(s), 4 ten-membered ring(s), 2 ester(s) (aliphatic) and 1 anhydride(s) (-thio). Learn more about Anthracene-maleic anhydride diels-alder adduct chemical structure at Mol In the present experimental work, the energy of combustion of the crystalline Diels-Alder adduct of anthracene and maleic anhydride: C 18 H 12 O 3, was measured with a model 1241 Parr automatic calorimeter and a Parr model 1710 calorimeter controller.The standard molar enthalpy of combustion of the (anthracene + maleic anhydride) adduct at p o = 0.1 MPa was â ¦ In this lab, the 4 electrons dienophile (maleic anhydride) to give the polycyclic Diels-Alder product.
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Spectral Code of Anthracene with. Maleic Anhydride prepared by L. G. Wade, Jr., Whitman College. Use the Diels-Alder reaction to form a bridged polycyclic anhydride. Write out the chemical equation for the Diels-Alder reaction of anthracene with maleic anhydride, showing structures of the reactants and the product. Thank. substituted anthracene, obtained by reacting the corresponding anthracene derivative with maleic anhydride (Scheme 2). The total assignment of protons and The maleic anhydride-anthracene adduct (about 9 g.) is removed by filtration, and the brown filtrate is refluxed for 2 hours with 80 ml.