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Preparing benzoic acid
Synthesis lab report
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Soran, Quinn Dr. Jeffrey Engle Chemistry 263 5/1/16 Synthesis Project Post-laboratory Report 1. For this experiment, three separate pathways were designed to utilize the exact same reagents in different orders to create a synthesis from acetophenone to methyl m-nitrobenzoate. This experiment was constructed in this format to evaluate the efficiency and overall percent yield of each pathway to determine which is most effective in synthesizing methyl m-nitrobenzoate. The pathway implemented in this experiment used acetophenone as its starting material and converted it to benzoic acid. The benzoic acid was then nitrated to m-nitrobenzoic acid, and the m-nitrobenzoic acid transformed into methyl m-nitrobenzoate. Benzoic Acid The first reaction …show more content…
By comparing the overall percent yields based upon pathway, the statistically superior pathway proved to be the Red pathway, which also happens to be the synthesis pathway I implemented. I determined that this was the best pathway based on the mean, median, and maximum overall percent yields of each pathway and are shown on Table 2. I hypothesize that this pathway was most successful because of the order of the reagents used, specifically that the nitration was the second step. I hypothesize that the addition of the nitro group to the benzoic acid was more successful than other reaction pathways because the attached carboxylic acid group is a moderate deactivator and meta director, more so than the attached ketone in the Blue pathway or the attached ester in the Green …show more content…
I would suggest to students performing the nitration to make sure their benzoic acid product is very fine and broken up before reacting it, as it has a tendency to clump together when it dries and thus proves very difficult to react in solution. I would also suggest keeping a very close eye on the temperature when adding the sulfuric/nitric acid mixture dropwise, as the reaction has a tendency to spike in temperature
The percent yield of products that was calculated for this reaction was about 81.2%, fairly less pure than the previous product but still decently pure. A carbon NMR and H NMR were produced and used to identify the inequivalent carbons and hydrogens of the product. There were 9 constitutionally inequivalent carbons and potentially 4,5, or 6 constitutionally inequivalent hydrogens. On the H NMR there are 5 peaks, but at a closer inspection of the product, it seems there is only 4 constitutionally inequivalent hydrogens because of the symmetry held by the product and of this H’s. However, expansion of the peaks around the aromatic region on the NMR show 3 peaks, which was suppose to be only 2 peaks. In between the peaks is a peak from the solvent, xylene, that was used, which may account to for this discrepancy in the NMR. Furthermore, the product may have not been fully dissolved or was contaminated, leading to distortion (a splitting) of the peaks. The 2 peaks further down the spectrum were distinguished from two H’s, HF and HE, based off of shielding affects. The HF was closer to the O, so it experienced more of an up field shift than HE. On the C NMR, there are 9 constitutionally inequivalent carbons. A CNMR Peak Position for Typical Functional Group table was consulted to assign the carbons to their corresponding peaks. The carbonyl carbon, C1, is the farthest up field, while the carbons on the benzene ring are in the 120-140 ppm region. The sp3 hybridized carbon, C2 and C3, are the lowest on the spectrum. This reaction verifies the statement, ”Measurements have shown that while naphthalene and benzene both are considered especially stable due to their aromaticity, benzene is significantly more stable than naphthalene.” As seen in the reaction, the benzene ring is left untouched and only the naphthalene is involved in the reaction with maleic
In addition to this, these compounds also display antagonist activity to calcium 23. For this reason, and for their associated pharmacological properties, a lot of interest and attention has been drawn to them in the recent years by researchers 22. A couple of methods have consequently been developed for the preparation of the octahydroquinazolinone derivatives 2. The most common of which include the Biginelli one pot reaction that involves urea/ thiourea, aromatic aldehydes and dimedone 24. Other methods include synthesis with the help of catalysts like concentrated sulfuric acid, Nafion-H, ionic liquid, and TMSCI 24. Synthesis in low ethanol could also be adopted but it is characterized with product yields that are between 19-69% and these are
Cu (aq) + 2NO3 (aq) + 2Na+ (aq) + 2OH- (aq) → Cu(OH)2 (s) + 2Na+ (aq) + 2NO3(aq)
and Gram-negative bacteria.[139] Mannich reaction also plays a significant role in bioactive skeleton target synthesis. Chernov et al. reported the synthesis of alkaloid-like molecules 22 and 23 from lambertianic acid via Mannich-type intramolecular ring closure reaction (Figure 6).[140]
...nt were quite successful. There were only a couple of mistakes that were committed including over titrating in phase 1 and inaccurate measurements of many substances. However, our results did not differ that much from the actual value and phase 2 went very successfully because we found the amount of NaOH needed to standardize the acid. Overall, I would consider this lab a success because we found the molarity, the amount of moles, the pKa, the ka, the equivalence points, and the molecular weight that did not differ that much from maleic acid. Maybe next time, we could make sure none of our equipment were contaminated and we could take our time with phase 1 of the experiment. Our percent error was just above 5 %, probably due to the fact of the contaminations and inaccurate measurements that were partaken in.
[11]: Selective catalytic reduction of nitric oxide by hydrocarbons Michael D. Amiridisa, Tiejun Zhanga, Robert J. Farrautob, Applied Catalysis B: Environmental, Volume 10, Issues 1–3, 14 September 1996, Pages 203–227
Ensure gloves are worn at all times when handling strong acids and bases within the experiment of the preparation of benzocaine. 4-aminobenzoic acid (3.0g, 0.022 moles) was suspended into a dry round-bottomed flask (100cm3) followed by methylated sprits (20 cm3). Taking extra care the concentrated sulphuric acid of (3.0 cm3, 0.031 moles) was added. Immediately after the condenser was fitted on, and the components in the flask were swirled gently to mix components. It should be ensured that the reactants of the concentrated sulphuric acid and the 4-aminobenzoic acid were not clustered in the ground glass joint between the condenser itself and the flask. In order to heat the mixture to a boiling point, a heating mantle was used and then further left for gently refluxing for a constituent time of forty minutes. After the duration of the consistent forty minutes the rou...
As a final point, the unknown secondary alcohol α-methyl-2-naphthalenemethanol had the R-configuration since it reacted the fastest with S-HBTM and much slower with R-HBTM. TLC was a qualitative method and ImageJ served as a quantitative method for determining which reaction was the faster esterification. Finally, 1H NMR assisted in identifying the unknown from a finite list of possible alcohols by labeling the hydrogens to the corresponding peaks.
yield of the pure product was determined to be 95.42%. PURPOSE The purpose of this lab was to perform an electro-philic aromatic substitution and determine the identity of the major product. TLC was used to detect unreacted starting material or isomeric products present in the reaction mixture. RESULTS The theoretical yield of the m-nitrobenzoate was determined to be 4.59 grams.
Chemical reactions: Consultation/reference to literature should be considered as the use of well documented chemical reactions for the synthetic route will lead to higher yields and less impurities.
In this experiment, the following chemicals were used; benzocaine, benzoic acid, ethyl acetate, sodium hydroxide, acetone, sodium benzoate, hydrogen chloride, methylene chloride, and glacial acetic acid.
As the use of paracetamol increased, scientists and reserachers have looked into the most efficient methods of synthesizing the compound. In 1997, demand for paracetamol in the United States was estimated at 30-35 thousand tons per year(IARC 73). Global demand was similarly heavy in many other countries. There are numerous synthetic pathways that are presently known that seek to produce the compound most efficient manner. In determining efficiency, the many factors must be taken into account. The most important ones include the cost of the reagents,...
Gilbert, C. John; Martin, F. Stephen. 2011. Experimental Organic Chemistry: A Miniscale and Microscale Approach. 5th Edition. Cengage Learning. pp.
H. Fischer. Organic Syntheses Coll. 1943, 2, p. 202; H. Fischer. Organic Syntheses Coll. 1935, 15, p. 17.
1) By oxidation: Aromatic acids can be obtained by the oxidation of ‘side chain’ of benzene derivatives.