Maleic anhydride underwent the Dials-Alder reaction with distilled cyclopentadiene as the dienophile. The reaction was a cycloaddition which produced cis-Norbornene-5,6-endo-dicarboxylic Anhydride surface. (1) Product one had a mass of 9.351 grams and product two had a mass of 9.572 grams. The theoretical yield was found to be 10.047 grams, which makes the percent yield to be 93.07%. Melting Points were found to confirm the purity of the product. Product one had a melting point of 163.7-164.8°C. Product two had a melting point of 162.2-163.9°C. IR Spectroscopy (nujol) are carbonyl peaks (1773.4 cm-1), Sp3 C-H peaks (2921.5 cm-1), Sp2 C-H (3000 cm-1). The carbonyl peaks prove the presence of an acid anhydride. H’NMR (CDCL3) …show more content…
Methylene chloride is added to the flask with the diester. The seperatory funnel is attached to the flask with 1.0 M bromine inside. Bromine is added to ester mixture drop by drop until the solution stays a yellow color. After ten minutes a cyclohexene and methylene chloride mixture is added drop by drop to remove the excess bromine. Ester solution is placed on the rotary evaporator at 45°C. Ethanol was added to the product. Solution was cooled in an ice bath for thirty minutes and crystals began to form. Solution was vacuum filtered with a Hirsch funnel. The mass of the product was 0.47 g. MP 70.1-75.3°C The theoretical yield was .74 g. This makes the percent yield 64%. The expected melting point was 123-125°C. The diacid was not the product formed. With IR, HNMR, and CNMR data the identity of the final product was found. IR (neat) 2989.8 and 2955.7 (Sp3 C-H), 1785.8 (Lactone ester), 1735.8 (ester). 1H NMR (CDCL3) 5.073 ppm (d, 1H), 4.991 ppm (d, 1H), 4.637 ppm (d, 1H), 4.599 ppm (d, 1H), 3.764 ppm (s, 3H), 3.364 ppm ( m, 1H), 3.130 ppm (m,1H), 2.948 ppm (d, 1H), 2.558 ppm (m, 2H), 2.363 ppm ( m, 1H), 1.934 ppm (s, 1H), 1.728 ppm (s, 1H). 13C NMR (CDCL3) 177.037 ppm, 171.388 ppm, 88.171 ppm, 53.125 ppm, 50.270 ppm, 49.297 ppm, 49.328 ppm, 49.040 ppm, 41.317 ppm, 36.441
After synthesizing tert-butyl chloride, the melting point on the compound was found to be 47˚C. According to literature, tert¬-butyl chloride has a melting point of 51˚C, apart from a little bit of deviation, this shows that the correct compound was created. The percent yield obtained for the synthesis of tert-butyl chloride was 47.42%. This could have been due to errors that occurred in the lab. When moving the solution from one test tube or graduated cylinder to another some of the solution may still be left in the tube which lowers the percent yield. Also when working with a simple distillation setup, the vial is not distilled to dryness therefore some of the solution is not collected. Some of the solution can also be trapped on the side
Dimethyl Fumarate was not successfully created during the course of this particular experiment, likely because of a failure of the bromine to mix with the other components of the test tubes. It was observed that the bromine had formed a separate fraction at the top of the rest of the test tube contents, and because of this the necessary reaction could not occur in substantial amounts for a precipitate of dimethyl fumarate to form. The amount of bromine that was in contact with the dichloromethane and dimethyl maleate was simply too small for a significant reaction to occur. The data discussed below is sourced from Alexander Boley. Alex reported the melting point range to be 94-97°C, with an accepted range of 102-105°C. The lower boiling point is most likely due to the compound not being dried sufficiently before the melting point was tested. Alex also reported isolating 0.348 grams of dimethyl fumarate. Since he utilized 0.5 g of dimethyl maleate solution, and the accepted density of dimethyl maleate is 1.153 g/ml, the theoretical maximum amount of dimethyl fumarate that could have been obtained is 0.5765 g; dimethyl fumarate would be present in the same amounts as it's steroisomer because of their identical constitution, so dimethyl maleate's density is a valid input for calculating the final amount of product. The result indicates that his percent yield was 60.36%. The percent loss indicated could be attributed to
After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some
8. ISBN: 0-558-05245-2 Virtual ChemLab: General Chemistry, Student Lab Manual/Workbook, V. 2.5, Third Edition, by Brian F. Woodfield and
The stilbene dibromide precipitated immediately as small plates. The mixture was cooled under tap water helping crystals form. The mixture was cooled before collecting the product by a vacuum filtration. For the crystals not to stick in the flask, the solution was washed with small amounts of ice cold methanol. When done pouring, the isolated solid dried for a few minutes in the filtration. To increase drying time, the crystals were pressed down. When the solid was collected, data such as melting point, percent yield and infrared spectroscopy spectrum values were collected.
Starting with 8.03 grams of maleic anhydride crystals, the students successfully converted them into two isomers of butenedioic acid. From the experiment, the students learned that maleic acid converts to fumaric acid in the presence of a proton. Little occurred during the reaction between the maleic anhydride and water. The solution remained clear during the heating. Moreover, all the crystals produced during the experiment are white and brittle. Furthermore, the students obtained 6.09 grams of maleic acid, the crystals produced in the first part of the lab and 0.90 grams of fumaric acid, the crystals produced in the second part of the lab. During the melting point test, the crystals of maleic acid begin melting at 121oC and fully melted
Within the field of Organic chemistry the Diels-Alder reaction is a method to create six membered rings by reacting a s-cis-diene with an alkene. The reaction occurs using the pi electrons present from the diene (4 pi electrons) and the alkene (2 pi electrons) to create a six membered ring in a concerted (one step) mechanism. This reaction is stereospecific, creating the endo product when the diene is part of a ring and the alkene has a cis configuration. When the diene is not part of a ring the product maintains the stereochemistry of the reactants. The particular reaction done in the lab reacted butadiene sulfone and maleic anhydride to create 4-cyclohexene-cis-1,2-dicarboxcylic acid. Since the reactant Butadiene sulfone is a gas at room temperature it was first reacted with heat to create 1,3-butadiene (a solid cis diene), which was then reacted with maleic anhydride to give the product. The resulting product was identified using IR as the reactants have no sp3-hybridized carbons and the product has four sp3 carbons. The product was also assessed for purity using melting point.
The week after, a recrystallization was performed on the previous week’s crude product. The product ethereal solution was first heated on a steam bath until dry. During the heating, a beaker of methanol was collected and also placed on the steam bath. Once the product was dry, it was cooled to room temperature and then placed in an ice-water bath. The now boiling methanol was added to the crude crystals and a recrystallization was performed. Once completed, the now purified product was collected via Buchner vacuum filtration and stored in drawer to dry for a week. Afterwards, a melting point range of the purified product was obtained by using a Mel-temp apparatus. Lastly, an
Results Synthesis. The synthesis of cyclohexene by dehydrating cyclohexanol through distillation had a crude yield of approximately 75%, the overall yield being 56% after extraction. Infrared Spectroscopy (IR) and Gas Chromatography/Mass Spectrometry (GC/MS) results indicate the presence of cyclohexanol in the product; therefore, the reaction did not go to completion. However, the spectra do display peaks characteristic and expected for cyclohexene, suggesting that the intended material was indeed synthesized but possibly in low concentrations.
In Figure 7, we can see the IR presenting peaks that represent different functional groups of the Acetanilide sample. The data collected and represented in Table 5, show that we found some functional groups that coincide with the structure of acetanilide. The peak that gave a wavelength of 3749.97 cm-1 is reflection of a Hydroxyl group which is in the structure of Acetanilide. The acetanilide sample also gave of a wavelength at 1683.85 cm-1 which is representative of a benzene functional group. In Table 6, we see the peaks at 1660.73 cm-1 and 1595.97 cm-1 that represent a Carbon double bonded with an Oxygen, and a Carbon-Carbon bond respectively.
The crude weight of the product formed was 0.067 grams. The theoretical mass that was used to calculate percent yield was calculated using the weight of norbornene, 0.519g and converting it to a product weight of exo-norborneol, which was calculated to be 0.620g. The percent yield was then calculated to be 10.81%, which can be found in table 3. A melting point was determined from the crystals formed in the vial by using a DigiMelt melting point apparatus. The melting point for the crystals was 90.0-106.8°C with a range of 16.8°C, which can be found in table 2.
A white powderish anthracene and white somewhat-crystallized maleic acid were used as starting product to yield 9, 10-dihydroanthracene-9, 10-succinic anhydride via diels-alder mechanism. A very simple and easy reflux technique was used to run the reaction followed by recrystallization. There was
The condensation product of primary amines with active carbonyl compounds have resulted in the formation of Schiff base compound. This has been reported by Hugo Schiff in 1864. Schiff base compound contain azomethine -C≡N with a general formula RHC=N-R’ where R and R’ are alkyl, aryl, cyclo alkyl or heterocyclic groups which may be variously substituted. These compounds are also known as anils, imines or azomethines (Mishra N. et al, 2013). Structurally, a Schiff base is a nitrogen analogue of an aldehyde or ketone in which the carbonyl group (C=O) has been replaced by an imine or azomethine group (Figure 1.1) (Abu-Dief M.A et al, 2015).
Rubeanic acid was purchased from sigma aldrich chemical company. 1H NMR spectra were recorded on a Mercury (300 MHz) spectrometer with TMS as internal standard. Mass spectra
Amino group of Compound NSC_211930 formed the hydrogen bonding with Ala162 a hinge region amino acid. While the amide group formed the hydrogen bond with Asp223. Lys111 involved in cation-pi interaction. Compound NSC_24871 formed the hydrogen bond interaction with Lys111,Ser160 and Ala 162. The phenyl ring of compound is sandwiched in between the phenyl rings of Tyr161 and Phe93 and they formed the pi-pi interaction. Tyr161 formed pi-pi interactions with phenyl ring of Compound_218342. While the carboxyl group involved in formation of two hydrogen bond with Lys111and Phe94.Phenolic oxygen was involved in formation of hydrogen bond with Ser162 & Ala162 amino acids. In all cases Try 161 involved in forming pi-pi interaction with the phenyl ring of the compounds. 2D representation of molecular docking results of all three compounds were shown in the Figure 7. Lys111 formed two hydrogen bonds with the two different oxygen atom of phenyl groups of the Compound NSC_24871.Apart of this one phenolic oxygen formed the two hydrogen bonds with the two hinge regions amino acids i.e. Ser160 & Ala162. These three compounds were retrieved from two databases (NCI& Maybridge) showed good interactions with important amino acids in the active stites.Among all three compounds, Compound NSC_218342 retrieved from the NCI database have exposed