Anthracene acts as the diene and maleic anhydride functions as the dienophile. Cyclopentadiene and maleic anhydride. This week you’re going to react cyclopentadiene with maleic anhydride to form the Diels-Alder adduct: You will dissolve ~4g of maleic anhydride (be sure to measure the exact amount) in ~15 mL of ethyl acetate (EtOAc) in a 125mL Erlenmeyer flask. It will dissolve in water and evaporates quickly from water and soil surfaces. Give a detailed mechanism (show electron flow) for the Diels-Alder reaction for the synthesis of cis-norbornene-5,6-endo-dicarboxylic anhydride from cyclopentadiene and maleic anhydride. IDENTIFICATION: 1,3-Cyclopentadiene has an irritating terpene like odor. Maleic anhydride is very soluble in water and readily reacts with water to form maleic acid.USE: Maleic anhydride is used to make other chemicals that are used in resins, dyes, drugs and agriculture. moles cyclopentadiene = mass / MM = 0.80 / 66.10 = 0.01210 moles. Question 4: Below is a generalized Diels-Alder reaction: A student wanted to carry out a Diels-Alder reaction [4 + 2] cycloaddition between Cyclopentadiene (1) (MW=66.10 g/mol) and Maleic anhydride (2), to make the compound (3) shown below. Although there are four stereogenic centres in the product only two diastereoisomers can be formed, any others are impossibly strained. And although it may seem tempting to believe that maleic anhydride can do that too, it is in an s-trans conformation, which isn't favorable in the Diels-Alder reaction, so I would only choose the cyclopentadiene dimerization as a plausible side product. The reaction of cyclopentadiene and maleic anhydride to produce cis-norbornene-5,6-endo-dicarboxylic anhydride is a 1:1 reaction, one mole of cyclopentadiene reacts with one mole of maleic anhydride. In the addition of cis-butanedioic anhydride (maleic anhydride) to cyclopentadiene there are two possible ways that the diene and the dienophile could come together to produce different products. The Diels-Alder reaction that you will be performing between cyclopentadiene and maleic anhydride occurs rapidly at room temperature. 5. USE: 1,3-Cyclopentadiene is used in the manufacturing of resins. Click the structures and reaction arrows in sequence to view the 3D models and animations respectively. Your reagents react in a 1:1 ratio, so we can see that the maleic anhydride is your limiting reagent as once all of the 0.01025 moles have reacted, there will still be 0.00185 moles of cyclopentadiene left over. Maleic anhydride is a classic substrate for Diels-Alder reactions. 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 has an irritating, choking odor. Through these calculations we can see that the cyclopentadiene is the limiting reagent is the cyclopentadiene because the reaction between cyclopentadiene and maleic anhydride is a 1:1 reaction. You should notice that both of them have three double bonds. It is a colorless liquid. Thus, the maximum amount of moles of cis-Norbornene-5, 6-endo-dicarboxylic anhydride we can produce is: The student finds an old bottle of cyclopentadiene sitting in one of the shelfs and attempts the synthesis of (3). Give balanced equations for both retro Diels-Alder reaction and the Diels-Alder reaction that you plan to do in this lab. IDENTIFICATION: Maleic anhydride appears as colorless needles or white lumps or pellets. These are shown in Equations 13-3 and 13-4: In practice, the adduct with the endo\(^2\) configuration usually is the major product. To the Craig tube, add 0.8 mL of reagent grade ethyl acetate and 175 mg of maleic anhydride. It is very possible that cyclopentadiene can dimerize. It is through this reaction that maleic anhydride converted to many pesticides and pharmaceuticals. moles maleic anhydride = mass / MM = 1.005 / 98.06 = 0.01025 moles. In this case both the diene and dienophile have stereochemistry. 1,3-Cyclopentadiene will polymerize to form dicyclopentadiene in a short time at room temperature. 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, as shown in the reaction below. Let the maleic anhydride dissolve in the EtOAc, by heating if necessary. To aid in product isolation, the entire reaction will be carried out in the Craig tube. In this example there are 0.0713 moles of cyclopentadiene and 0.0634 moles of maleic anhydride and so the limiting reagent is maleic anhydride …
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