Cis-norbornene 5,6-endo-dicarboxylic anhydride, also known as ENDO-5,6-cis-norbornene dicarboxylic anhydride or ENDO-NDA for short, is a chemical compound with the molecular formula C10H8O3. It is an anhydride of cis-norbornene-5,6-dicarboxylic acid and is used as a starting material in the synthesis of a variety of polymers and other chemical compounds.
ENDO-NDA is a solid compound with a melting point of around 120-122°C. It is poorly soluble in water, with a solubility of only 0.07 g/L at 25°C. However, it is more soluble in organic solvents such as acetone, chloroform, and benzene, with solubilities of 4.9 g/L, 3.2 g/L, and 2.5 g/L, respectively, at 25°C.
ENDO-NDA has a number of potential applications in the chemical industry, including the synthesis of polymers such as polyimides, polyesters, and polyamides. It is also used in the production of coatings, adhesives, and other industrial materials.
One of the main challenges in using ENDO-NDA is its low solubility in water, which can make it difficult to dissolve and work with in aqueous solutions. This low solubility is due to the presence of a highly hydrophobic aromatic ring in the compound's structure, which resists solvation by water molecules.
To overcome this solubility challenge, ENDO-NDA can be dissolved in organic solvents such as acetone or chloroform, which have a higher affinity for the compound and can dissolve it more readily. However, care must be taken when working with organic solvents, as they can be flammable and potentially hazardous to handle.
In conclusion, cis-norbornene 5,6-endo-dicarboxylic anhydride is a solid compound with a low solubility in water but good solubility in organic solvents. It has a number of potential applications in the chemical industry, but its low solubility in water can pose challenges in its use and handling.
Top head with Claisen air condenser then attach thermometer with adapter. In the case of cyclopentadiene and maleic anhydride, the reaction takes place quite quickly due to the many electronegative oxygen present in both reactants. Thus, the maximum amount of moles of cis-Norbornene-5, 6-endo-dicarboxylic anhydride we can produce is: Now that the theoretical yield has been calculated, we can compare the experimental yield with the theoretical yield: Discussion: The literature value for the melting point of cis-Norbornene-5, 6-endo-dicarboxylic anhydride is 165º C. We were only able to produce a yield of 20. The Hansen solubility parameter was used for explaining the solubility order of carbic anhydride in selected solvents. This is final step in the multistep synthesis pathway to form hexaphenylbenzene, and uses the products of the previous experiments: benzil and diphenylacetylene… Diels Alder Reaction Lab In this experiment a Diels-Alder reaction was used to form the products.
We were able to form cis-Norbornene-5,. More than one ring can be formed when the reaction is intramolecular. Thus, the maximum amount of moles of cis-Norbornene-5, Now that the theoretical yield has been calculated, we can compare the experimental yield with the theoretical yield: Discussion The literature value for the melting point of cis-Norbornene-5, 6-endo-dicarboxylic anhydride is 165º C. Clay catalysis: A convenient and rapid formation of anhydride from carboxylic acid and isopropenyl acetate under microwave irradiation. Some documentation and label information may refer to the legacy brand.
This reaction can form new carbon-carbon bonds and new stereocenters. These reactions give great yields while not requiring a metal catalyst. For the following experiment, the main focus is the use of a cycloaddition reaction, also known as Diels-Alder. Get your paper price 124 experts online Mechanism: Side Reaction: Experimental: Table of Chemicals: Cyclopentadiene Maleic Anhydride Ethyl Acetate Hexane 66. This reaction is best used for making six membered rings with different functional groups. This is a single-step reaction where two pi-bonds switch to two sigma-bonds. Some of these dienes are conjugated and have the ability to make Diels-Alder adducts with maleic anhydride.
This type of reaction was named for Otto Diels and Kurt Alder who were the first to investigate this reaction Weldegirma, 2012. Causes serious eye damage. The calculations for the percent yield are as follows: First, the moles of the reactants must be calculated: 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. One reactant the diene contributes four carbons and the other reactant the dienophile, in this case the maleic anhydride contributes two carbons to the six-membered ring of the resulting cyclic compound the adduct. Even though our crystals did not turn out as we had hoped, the melting point range for our crystals was very close to the literature value. Precautionary Statements: 33784-P272-P280-P285-P302+P352-P304+P341-P305+P351+P338-P310-P333+P313-P342+P311-P363-P501c Contaminated work clothing should not be allowed out of the workplace. The two undergo a Diels-Alder reaction to produce norbornene-cis-5,6-dicarboxylic anhydride, as shown: Figure 2: Diels-Alder reaction between cyclopentadiene and maleic anhydride H O H H H H O + O H O + H O O O O O H cyclopentadiene maleic anhydride Cited: 1 2 3 Durst, H.
The Diels-Alder reaction is the conjugate addition of an alkene to a diene. The reaction is called a 4+2 cycloaddition because a ring is formed by four pi electrons in the diene interacting with two pi electrons of the alkene or alkyne Wade, Jr. Enantioselective Ribozyme Catalysis of a Bimolecular Cycloaddition Reaction. The dissolution process was always endothermal and entropy-driven. The Diels-Alder reaction has high synthetic utility for making unsaturated 6-membered rings Kahn, 2011. In order to un- dimerize dicyclopentadiene, it must be heated to just under its boiling point to make fresh cyclopentadiene.
Dicyclopentadiene would not result in the desired product, cis-Norbornene-5, 6-endo-dicarboxylic anhydride, so this must be remedied. Maleic anhydride was the electron poor dienophile used in the reaction. This technique can be used as a tool to instruct organic + 1,3-butadiene ethene cyclohexene In the case of the reaction outlined in this report, the substituted alkene is maleic anhydride, and the conjugated diene is cyclopentadiene. This reaction is so important because of its ability to form new carbon-carbon bonds. IF IN EYES: Rinse cautiously with water for several minutes. This reaction is so important because of its ability to form new carbon-carbon bonds. To increase the speed of the reaction, xylene was used because of its high boiling point.
With our melting point being so close to the literature value for cis-Norbornene-5, 6-endo-dicarboxylic anhydride, it is very likely that the desired product was obtained. Even though our crystals did not turn out as we had hoped, the melting point range for our crystals was very close to the literature value. Put mineral oil in a 5 mL short-necked, round-bottomed flask until round portion is half full. Add additional ice if needed but do not allow to get in flask. The experimental value we obtained through the Diels- Alder reaction was 160- 163º C.
Causes serious eye damage. Reference Table for compounds used in Diel-Alder lab. Diels-Alder reactions are useful in the creation of medicine, rubber, and plastic. To prove that each stereoisomer was made in the experiment and to distinguish between the two molecules, the characteristic long range coupling affects seen in the H1-NMR spectra of bridged six member ring molecules are used. Melting point of the product was also determined to verify the correct product was obtained and to check the purity of the product. We were able to form cis-Norbornene-5, 6-endo-dicarboxylic anhydride crystals and were able to achieve a very pure product. This reaction does not seem to be very efficient at all.
Solubility of cis-5-norbornene-endo-2,3-dicarboxylic anhydride carbic anhydride in fourteen pure solvents including methyl acetate MAC , ethyl acetate EAC , n-propyl acetate NPAC , isopropyl acetate IPAC , n-butyl acetate NBAC , n-amyl acetate NAAC , isoamyl acetate IAAC , hexyl acetate HAC , octyl acetate OAC , ethanol EtOH , 1,4-dioxane, 1-methyl-2-pyrrolidinone NMP , acetone, N, N-dimethylformamide DMF and three binary solvents of DMF + EtOH , 1,4-dioxane + EtOH and EtAC + EtOH with various mass fractions was experimentally studied at various temperatures under 0. GHS H Statement H334-H318-H317 May cause allergy or asthma symptoms or breathing difficulties if inhaled. P261-P272-P280-P285-P302+P352-P304+P341-P305+P351+P338-P310-P333+P313-P342+P311-P363-P501c H317-H318-H334 EINECSNumber : 204-957-7 RTECSNumber : DT5600000 TSCA : No Recommended Storage : Ambient temperatures. The reaction takes place between the two pi electrons from the dienophile and the 4 pi electrons from the diene; what happens is the bonds react together in order to form new single bonds because they are more stable, in terms of energetics Diels-Alder Reaction. It was not clear if a pure product had been formed because time constraints did not allow us to perform thin layer chromatography. This reaction can form new carbon-carbon bonds and new stereocenters. This type of reaction was named for Otto Diels and Kurt Alder who were the first to investigate this reaction Weldegirma, 2012.
The Diels- Alder reaction is one of the most important reactions in all of organic chemistry because of the applicability of it. Remove contact lenses, if present and easy to do. References: 1 Reusch, Rosetta N. May cause allergy or asthma symptoms or breathing difficulties if inhaled. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry.