The Knorr Synthesis of Pyrroles Experimental A mixture of ethyl acetoacetate 1 (7.52 g, 7.5 mL) in glacial acetic acid (18 mL) was prepared and cooled to 5oC while stirring. Sodium nitrate solution (2.1 g in 5 mL deionised water) was added at such a rate that the temperature of reaction did not exceed 7oC. Once this addition was complete the mixture was stirred with cooling for 10 minutes before being allowed to warm to room temperature. Zinc dust (4.0 g) was added to the reaction mixture in small portions so that the mixture refluxed gently, the reaction mixture was then heated to reflux for one hour. The mixture was then allows to cool and the excess zinc to settle. While still hot the solution was decanted into stirred cold water (200 mL) precipitating the crude product. The zinc residue was washed with warm glacial acetic acid (2 x 5 mL) and this was added to the aqueous solution. This suspension was allowed to stand for 10 minutes, before being filtered, washed (water 2 x 10 mL) and air dried. The crude product was recrystallised from ethanol to yield a yellow solid 3. 26% yield (1.83 g); Elemental analysis for C12H17NO4: C: 54.918%, H: 6.704%, N: 5.122% (Theoretical: C: 60.24%, H: 7.16%, N: 5.85%, Loss:26.75%); Mr 239.2 g mol-1; ν/cm-1: 1259.48 (N-C), 1667.41 (C=C), 1688.41 (C=O), 2976.58 (C-H), 3265.02 (N-H); 1H-NMR (400 MHz, CDCl3), δ/ppm: 1.24 and 1.38 (dt, 3H, C-CH3, C12 and C15), 2.51 and 2.56 (ds, 6H, 2 x =C-CH3, C6 and C7), 4.31 (m, 4H, 2 x -CH2-, C11 and C14), 5.3 (s, 1H, N5-H); 13C-{1H}-NMR (400 MHz, CDCl3), δ/cm-1:11.98 (C6 and C7), 14.43 (C12 and C15), 59.50 and 60.29 (C11 and C14), 133.5 (C3), 117.5 (C1), 131.3 (C2), 138.6 (C4), 165.47 (C8 and C9) . Results and Discussion Product 3 was formed i... ... middle of paper ... ...nal peaks in the spectrum are at much higher wavenumbers because of the lighter elements involved. The C-H stretch is at 2976.58 cm-1 and the N-H stretch is at 3265.02 cm-1. These peaks all correspond well with the literature values2. Conclusion Product 3 was isolated in a low yield of 27% and with some solvent impurities as shown by the analytical techniques but it was indeed synthesised successfully. On repeating this experiment more care should be taken when purifying to remove the solvent impurities and minimise loss of crude product. References 1. H. E. Gottleib, V. Kotlyar and A. Nudelman, J. Org. Chem., 1997, 62, 7512. 2. E. Fabiano and B. T. Golding, J. Chem. Soc. Perkin Trans., 1991, 3371. Appendix 1 Figure 2 1H-NMR spectrum of product 3. Figure 3 13C-NMR spectrum of product 3. Figure 4 IR spectrum of product 3.
This paper describes the methods used in the identification, investigation of properties, and synthesis of an unknown compound. The compound was identified as calcium nitrate by a variety of tests. When the compound was received, it was already known to be one of twelve possible ionic compounds. The flame test identified the presence of the calcium anion in the compound. The compound tested positive for the nitrate cation using the iron sulfate test. At this point it was hypothesized that the compound was calcium nitrate. Reactivity tests and quantitative analysis comparing the unknown compound with calcium nitrate supported this hypothesis. Synthesis reactions were then carried out and analyzed.
In this case, the nitrate ion moved from one compound to another as the Cu was replaced by Zn. The zinc dissolved to form zinc (II) ions as the copper (II) ions came out of the solution as copper metal and deposited on the surface of the
The objective of this experiment was to perform extraction. This is a separation and purification technique, based on different solubility of compounds in immiscible solvent mixtures. Extraction is conducted by shaking the solution with the solvent, until two layers are formed. One layer can then be separated from the other. If the separation does not happen in one try, multiple attempts may be needed.
The IR spectrum that was obtained of the white crystals showed several functional groups present in the molecule. The spectrum shows weak sharp peak at 2865 to 2964 cm-1, which is often associated with C-H, sp3 hybridised, stretching in the molecule, peaks in this region often represent a methyl group or CH2 groups. There are also peaks at 1369 cm-1, which is associated with CH3 stretching. There is also C=O stretching at 1767 cm-1, which is a strong peak due to the large dipole created via the large difference in electronegativity of the carbon and the oxygen atom. An anhydride C-O resonates between 1000 and 1300 cm-1 it is a at least two bands. The peak is present in the 13C NMR at 1269 and 1299 cm-1 it is of medium intensity.
The theoretical yield of the m-nitrobenzoate was de-termined to be 4.59 grams. The actual amount of crude product was determined to be 3.11 grams. The percent yield of the crude product was determined to be 67.75 %. The actual amount of pure product formed was found to be 4.38 grams. The percent yield of the pure product was determined to be 95.42%. Regarding the thin layer chromatography, the line from the solvent front was 8 centimeters.
Distilled water was used to obtain water from the purest source. As well, the highest available concentration of isopropyl alcohol was purchased to get the most accurate results. Pure vegetable oil was used. All topped by completing the trial twice, this assures the results are confirmed and are highly accurate.
Then the reaction tube was capped but not tightly. The tube then was placed in a sand bath reflux to heat it until a brown color was formed. Then the tube was taken out of the sand bath and allowed to cool to room temperature. Then the tube was shaken until a formation of a white solid at the bottom of the tube. After formation of the white solid, diphenyl ether (2 mL) was added to the solution and heated until the white solid was completely dissolved in the solution. After heating, the tube was cooled to room temperature. Then toluene (2 mL) was added to the solution. The tube was then placed in an ice bath. Then the solution was filtered via vacuum filtration, and there was a formation of a white solid. Then the product was dried and weighed. The Final product was hexaphenylbenzene (0.094 g, 0.176 mmol,
The solutions were then stirred with separate stirring rods to mix the NaCl solution and the deionised water into a homogeneous solution.
Comment on class result with respect to differences in filter types, differences in filter assemblies, and overall on the confidence you would have in using this type of sterilisation process in preparation of pharmaceutical products. List the factors that may cause contamination during filtration. (20 marks)
...form 〖PbCrO〗_4 and then process it through a filter. After filtering the 〖PbCrO〗_4 I had to dry the 〖PbCrO〗_4 residue in the drying oven for 30 minutes at 80℃. Then let it cool for 5 minutes and weigh it and finally make a few calculations to obtain the theoretical, actual, and percent yields of 〖PbCrO〗_4. I was able to fulfill the experiment because I obtained all the answers to the equations in an accurate amount. I believe this experiment was a success due to my hypothesis of, If physical methods are used to separate 〖 PbCrO〗_4 precipitate from the reaction mixture then I can successfully calculate the theoretical, actual, and percent yields, being correct.
The conical vial was placed in a small beaker and allowed to cool to room temperature. The mixture was Cooled thoroughly in an ice bath for 15-20 minutes and crystals collected by vacuum filtration on a Hirsch funnel. The vial was rinsed with about 5 mL of ice water and transferred into to the Hirsch funnel and again washed with two additional 5mL portions of ice water. Crystals were dried for 5-10 minutes by allowing air to be drawn through them while they remained on the Hirsch funnel. The product was transferred to a watch glass plate and allow the crystals to dry in air. Crude acetaminophen product was weighed and set aside a small sample for a melting point determination and a color comparison after the next step. Calculation of the percentage yield of crude acetaminophen (MW = 151.2). was done and recorded in the lab notebook.
Benzyl bromide, an unknown nucleophile and sodium hydroxide was synthesized to form a benzyl ether product. This product was purified and analyzed to find the unknown in the compound.
To investigate the temperature change in a displacement reaction between Copper Sulphate Solution and Zinc Powder
Remove the extra solvent on a steam bath under a hood while flushing the flask with N2 gas, leaving the crude extract. Weigh extract.
H. Fischer. Organic Syntheses Coll. 1943, 2, p. 202; H. Fischer. Organic Syntheses Coll. 1935, 15, p. 17.