The synthesis of .525 g of para-methoxyacetophenone and .49 g of para-chlorobenzaldehyde using 95% ethanol and catalytic aqueous sodium hydroxide yielded .587 g (61.7% yield) of chalcone 1. The product of chalcone 1 was then confirmed through several different tests. Testing with TLC showed that the product contained a pure substance with only one dot present. The melting point was tested and showed similar characteristics to that of the literature melting points2. The 1H-NMR was analyzed and the key characteristics of the integration values and chemical shifts were comparable to that of the desired chalcone 1 product. Infrared spectroscopy (IR) supported the claim due to the fact that the product’s wavelengths displayed peaks representing characteristics found in the chalcone 1 product. Mass spectrometry was used to confirm the presence of chlorine in our product and to analyze the cation fragments and compare to potential structures. Lastly, this experiment implemented the green chemistry concepts of using safer solvents and a high atom economy while aiming to achieve a high yield product. The TLC analysis of the recrystallized product along with the two …show more content…
The presence of the strong peak at 1602 cm-1 supports the claim that there is an aromatic ring located in the product. Another piece of evidence to support the E1cB reaction step is the presence of the strong alkene C=C stretch (conj) located at 1628.2 ppm which supports the claim of the combination of the two reagents. Methoxy is represented in the product through the two peaks located at 1655.2 cm-1 and 1278.7cm-1 which shows that the Ketone C=O stretch (conj) and ether C-O stretch are located in the final product. Chloro is found in the product through the chlorine displayed as an alkyl halide C-Cl stretch in the product through the peak at 675.8
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 a separate beaker, acetone (0.587 mL, 8 mmol) and benzaldehyde (1.63 mL, 16 mmol) were charged with a stir bar and stirred on a magnetic stirrer. The beaker mixture was slowly added to the Erlenmeyer flask and stirred at room temperature for 30 minutes. Every 10 minutes, a small amount of the reaction mixture was spotted on a TLC plate, with an eluent mixture of ethyl acetate (2 mL) and hexanes (8 mL), to monitor the decrease in benzaldehyde via a UV light. When the reaction was complete, it was chilled in an ice bath until the product precipitated, which was then vacuum filtrated. The filter cake was washed with ice-cold 95% ethanol (2 x 10 mL) and 4% acetic acid in 95% ethanol (10 mL). The solid was fluffed and vacuum filtrated for about 15 minutes. The 0.688 g (2.9 mmol, 36.8%, 111.3-112.8 °C) product was analyzed via FTIR and 1H NMR spectroscopies, and the melting point was obtained via
The purpose of this experiment involved synthesis of diphenylmethanol using phenylmagenisum bromide and benzaldehyde, using the method called Grignard reaction. Grignard reactions are an important method for new carbon-carbon bond formation as well as for the synthesis of alcohols.
The identity of the product was trans-2,3-dibromo-3-phenylpropanoic acid, and it was concluded to be this from melting point data. This product resulted from an Anti Addition mechanism.
The product that is formed the most is 1-methyl-1-cyclohexexene because it is the most highly substituted and thus the most stable, while 3-methyl-1-cyclohexene and methylenecyclohexane are produced less because they are less highly substituted and thus less stable. This reaction proceeded through an E1 pathway. In the mechanism the sulfuric acid provides a proton which protonates the hydroxyl group on the 2-methylcyclohexanol. This forms a good leaving group on the 2-methylcyclohexanol which leaves the compound as water. A carbocation results and H2PO4^- deprotonates a hydrogen on a carbon atom next to carbon atom with a positive charge resulting in alkenes with the major and minor products. One major technique used in this experiment was distillation. The reason distillation works is because different organic compounds have different boiling points. Usually a mixture containing two compounds is placed in the round bottom flask in the distillation apparatus. When the distillation apparatus is turned on and heat is applied, the vaporization of the compound in the mixture with the lower boiling point occurs. This compound, then condenses in the condenser and is received by the receiving flask at the end of the distillation
In this lab, iron filings and copper sulfate pentahydrate were chemically reacted to produce iron sulfate and copper.
During this week’s lab, both the cis and trans enantiomers of 2-methylcyclohexanol will be produced through the reduction of 2-methyclcyclohexanone with sodium borohydride. Once the product is formed, NMR signals are used to examine the product of this reduction by observing the cis and trans location of the CH2OH group. The integration of the signal will then be examined and to show the ratio of cis and trans product that is formed through this reaction.
The Diels-Alder experiment was conducted in laboratory to produce a bridged polycyclic anhydride. The Diels-Alder reaction takes place to combine a diene; the electron rich nucleophile with a dienophile which is “diene loving”, with at least one strong electron-withdrawing group1. In this experiment, anthracene is used as the diene which combines with maleic anhydride, the dienophile, to form
The purpose of this experiment is to conduct an elimination reaction by dehydrating cyclohexanol to cyclohexane. The elimination reaction that is occurring in this experiment is an E1 reaction. An acid catalyst is used in the experiment because the alcohol functional group is a poor leaving group. The method used to achieve this reaction is to boil the azeotrope until it begins to distill into cyclohexene. Cyclohexene is removed from the mixture by keeping the distillation head below 90°C. After the purification of the product, the product will go under two addition reactions (bromine test and a permanganate test) and a IR spectrum. This will determine the identity and the characteristics of the product. The results of the bromine and permanganate
...teraction of the HOMO of the diene and the LUMO of the dienophile. This reaction was done at relatively low temperatures as the dry ether has a boiling point of 34.6 °C. At low temperature the endo preference predominates unless there is extreme steric hindrance, which in this case there is not. The endo product forms almost exclusively because of the activation barrier for endo being much lower than for exo. This means that the endo form is formed faster. When reactions proceed via the endo for the reaction is under kinetic control. Under kinetic control the adduct is more sterically congested, thus thermodynamically less stable. The endo form has a lower activation energy, however, the EXO form has a more stable product. As this is a symmetrical Diels-Alder reaction there is not two possible isomers of the product.
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,
Enzymes are proteins that consist of a long chain of different amino acids that increase the rate of chemical reactions by lowering activation energy. (Bbc, 2016) Activation energy is the minimum amount of energy required to activate molecules to undergo a chemical reaction, so lowering the activation energy enhances the chemical reaction, allowing it to occur faster and more often. (Encyclopedia Britannica, 2016) Chemical reactions happen within cells, with molecules called substrates. (Live Science, 2016) Two molecules must collide at the same time, with the right orientation and sufficient energy in order for the chemical reaction to occur. (Rsc, 2016) Once together the enzyme and substrates bind at the active site and the chemical reaction
Diphenyl ether, first gaining attention in the late nineteenth and early twentieth century, is an organic compound that belongs to the ether organic functional group with a molecular formula of C12H10O. Also referred to as 1,1’-Oxybisbenzene, biphenyl oxide, diphenyl oxide, phenyl oxide, phenyl ether, or phenoxybenzene, diphenyl ether consists of two phenyl rings attached by an oxygen atom. The structural formula appears in Figure 1. Phenyl rings, C6H5, are extremely similar to benzene rings, C6H6, and only differ in regards to being bonded to a different atom than hydrogen on one vertex of the ring. Thus, diphenyl ether undergoes reactions that are common of phenyl rings and ring structures in general. Until recently, diphenyl ether did not have any interesting properties worth exploration to scientists, but current research focuses on the application of the chemical as part of the conversion of solar energy into usable energy as a means of renewable energy. This particular organic compound represents an anomaly of the ether functional group, participating in various chemical reactions and having an industrial application aside from being a solvent.
To begin, the Ocean Optics UV/Vis spectrometer was connected to a laptop using the GoLink!, and then logger pro was opened to record the data. Next, the spectrometer was calibrated using a 1cm acrylic cuvette cleaned with deionized water. The cuvette was then filled with deionized water and placed into the sample chamber of the spectrometer. Experiment_Calibrate_Spectrometer: 1 was selected and then 6o seconds passed while the lamp in the spectrometer warmed up. Once the lamp was fully warm, the calibration was finished. The optically clear sides of the cuvette were not touched since that is where the light shines through. The green apple Gatorade was poured into the cuvette carefully, and the absorbance was measured by the spectrometer. The
In this experiment, Borneol was oxidized to Camphor and later reduced to two possible diastereomers, in which isoborneol was favored, with the use of sodium hypochlorite and sodium borohydride. Hypochlorous acid served as the oxidizing agent and was vital in the formation of the ketone making up the bicyclic compound Camphor. Second most important, sodium borohydride provided the reducing agent, hydride, which added in on the endo side of the second carbon (C2) to make the exo alcohol isoborneol. The mechanisms of oxidation and reduction mirrored similar reactions such as esterification, β-elimination, and nucleophilic attack. The chirality and stereochemistry was observed in each step and played a role in forming the exo product isoborneol