It has an irritating, choking odor. In this case both the diene and dienophile have stereochemistry. Anthracene acts as the diene and maleic anhydride functions as the dienophile. IDENTIFICATION: 1,3-Cyclopentadiene has an irritating terpene like odor. You should notice that both of them have three double bonds. 5. Give balanced equations for both retro Diels-Alder reaction and the Diels-Alder reaction that you plan to do in this lab. Although there are four stereogenic centres in the product only two diastereoisomers can be formed, any others are impossibly strained. 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. Thus, the maximum amount of moles of cis-Norbornene-5, 6-endo-dicarboxylic anhydride we can produce is: moles maleic anhydride = mass / MM = 1.005 / 98.06 = 0.01025 moles. 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. moles cyclopentadiene = mass / MM = 0.80 / 66.10 = 0.01210 moles. It is a colorless liquid. 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. 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. 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. IDENTIFICATION: Maleic anhydride appears as colorless needles or white lumps or pellets. It is through this reaction that maleic anhydride converted to many pesticides and pharmaceuticals. It is very possible that cyclopentadiene can dimerize. 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. 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. It will dissolve in water and evaporates quickly from water and soil surfaces. 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. To the Craig tube, add 0.8 mL of reagent grade ethyl acetate and 175 mg of maleic anhydride. 1,3-Cyclopentadiene will polymerize to form dicyclopentadiene in a short time at room temperature. Maleic anhydride is a classic substrate for Diels-Alder reactions. 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 … Cyclopentadiene and maleic anhydride. The Diels-Alder reaction that you will be performing between cyclopentadiene and maleic anhydride occurs rapidly at room temperature. USE: 1,3-Cyclopentadiene is used in the manufacturing of resins. The student finds an old bottle of cyclopentadiene sitting in one of the shelfs and attempts the synthesis of (3). 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. To aid in product isolation, the entire reaction will be carried out in the Craig tube. 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. 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. Let the maleic anhydride dissolve in the EtOAc, by heating if necessary. These are shown in Equations 13-3 and 13-4: In practice, the adduct with the endo\(^2\) configuration usually is the major product.
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