Converting 4-tert-butylcyclohexanol into 4-tert-butylcyclohexanone via oxidation reaction generated 0.270 grams. The product is confirmed through NMR. The second part of the experiment is to convert 4-tert-butylcyclohexanone into 4-tert-butylcyclohexanol via reduction reaction using the product obtained from earlier. However, due to the product having too many impurities, an industrial 4-tert-butylcyclohexanone was used for the experiment. The reaction generated 0.118 grams, a 99.2% yield rate. The NMR confirmed the product to be 4-tert-butylcyclohexanol, with a ratio of 85% trans and 15% cis isomers. In compare to the industrialized alcohol, it has almost the same ratio. Besides L-selectride, trans isomers are more common. The reason as
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
The goal of this two week lab was to examine the stereochemistry of the oxidation-reduction interconversion of 4-tert-butylcyclohexanol and 4-tert-butylcyclohexanone. The purpose of first week was to explore the oxidation of an alcohol to a ketone and see how the reduction of the ketone will affect the stereoselectivity. The purpose of first week is to oxidize the alcohol, 4-tert-butylcyclohexanol, to ketone just so that it can be reduced back into the alcohol to see how OH will react. The purpose of second week was to reduce 4-tert-butylcyclohexanol from first week and determine the effect of the product's diastereoselectivity by performing reduction procedures using sodium borohydride The chemicals for this lab are sodium hypochlorite, 4-tert-butylcyclohexanone
The weight of the final product was 0.979 grams. A nucleophile is an atom or molecule that wants to donate a pair of electrons. An electrophile is an atom or molecule that wants to accept a pair of electrons. In this reaction, the carboxylic acid (m-Toluic acid), is converted into an acyl chlorosulfite intermediate. The chlorosulfite intermediate reacts with a HCL. This yields an acid chloride (m-Toluyl chloride). Then diethylamine reacts with the acid chloride and this yields N,N-Diethyl-m-Toluamide.
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
Since, the expected weight was 50.63 mg the percent yield is 59.3%. A TLC was conducted on this final product and a faint spot of 4-tert-butylcyclohexanone still appeared in lane 3 of the plate; meaning the reaction did not fully go to completion. The Rf values were 0.444, 0.156, and 0.111, where the lowest value is the trans isomer and the highest value is the ketone. This affected the IR spectrum conducted by having a carbonyl group peak at 1715 cm-1 which should not be present if all the product was 4-tert-butylcyclohexanol. However, the IR spectrum still showed peaks at 3292 cm-1 (hydroxyl group), 2939 cm-1 (sp2 carbon bonded to hydrogen) and 2859 cm-1 (sp3 carbon bonded to hydrogen) which support the presence of the alcohol. The accepted melting point of 4-tert-butylcyclohexanol is in the range of 62 – 70˙C (Lab Manual). The two melting point measurements using the Mel-Temp® machine gave ranges of 57 – 61˙C and 58 – 62˙C, which is not exact due to some 4-tert-butylcyclohexanone being present that has a low melting point of around 47 – 50˙C
The three butene products have been verified to elute in the following order: 1-butene, trans-2-butene, and cis-2-butene. Theory: The dehydration of 2-butanol, a secondary alcohol, progresses readily in the presence of a strong acid like concentrated sulfuric acid (H2SO4). The reaction is completed via the E1 mechanism. Initially, the hydroxyl group is a poor leaving group, but that is remedied by its protonation by the acid catalyst (H2SO4) converting it to a better leaving group, H2O. The loss of this water molecule results in a secondary carbocation intermediate that continues to form an alkene in an E1 elimination.
After performing the second TLC analysis (Figure 4), it was apparent that the product had purified because of the separation from the starting spot, unlike Figure 3. In addition, there was only spot that could be seen on the final TLC, indicating that only one isomer formed. Since (E,E) is the more stable isomer due to a less steric hindrance relative to the (E,Z) isomer, it can be inferred that (E,E) 1,4-Diphenyl-1,3-butadiene was the sole product. The proton NMR also confirmed that only (E,E) 1,4-Diphenyl-1,3-butadiene formed; based on literature values, the (E,E) isomer has peaks between 6.6-7.0 ppm for vinyl protons and 7.2-7.5 ppm for the phenyl protons. Likewise, the (E,Z) isomer has vinyl proton peaks at 6.2-6.5 ppm and 6.7-6.9 ppm in addition to the phenyl protons. The H NMR in Figure 5 shows multiplets only after 6.5 ppm, again confirming that only (E,E) 1,4-Diphenyl-1,3-butadiene formed. In addition, the coupling constant J of the (E,E) isomer is around 14-15 Hz, while for the (E,Z) isomer it is 11-12 Hz. Based on the NMR in Figure 5, the coupling constant is 15.15 Hz, complementing the production of (E,E)
In this lab experiment, three milliliters of pure cyclohexane was placed within a test tube and lowered into an ice-water bath. The test tube had a temperature probe within it, which measured the cyclohexane lowering in temperature. Once the cyclohexane solution started to solidify, the cooling curve could be observed and the freezing temperature could be determined. The pure cyclohexane was then thawed, with 0.60 grams of biphenyl being added to the cyclohexane. The experiment was then run again. The result was a freezing point of around 8.6℃ for the pure cyclohexane and 7.0℃ for the cyclohexane-biphenyl solution. To confirm the results that the cyclohexane-biphenyl solution had a lower freezing point, the experiment was ran again. The results
The acid compound, which contain a carboxylic group is altered chemically when an aqueous sodium hydroxide, a strong base, is added to the mixture to change its distribution between a pair of solvent, methylene chloride and water. This reaction produce a salt, which contain a Na+ in its chemical structure that is soluble in water but not in our organic solvent, methylene chloride. Also this reaction will yield water, which is immiscible with most organic solvent. The salt will be soluble in water and the neutral compound will be mixed with methylene
Reacting 1-butanol produced 2-trans-butene as the major product. 1-butanol produces three different products instead of the predicted one because of carbocation rearrangement. Because of the presence of a strong acid this reaction will undergo E1 Saytzeff, which produces the more substituted
The spots moved 3.8cm, 2.3cm, 2.1cm, 1.8cm, and 2.5 cm, for the methyl benzoate, crude product, mother liquor, recrystallized product, and isomeric mixture, respectively. The Rf values were determined to be.475,.2875,.2625,.225, and.3125, for the methyl benzoate, crude product, mother liquor, recrystallized product, and isomeric mixture, respectively. Electron releasing groups (ERG) activate electrophilic substitution, and make the ortho and para positions negative, and are called ortho para directors. In these reactions, the ortho and para products will be created in a much greater abundance. Electron Withdrawing groups (EWG) make the ortho and para positions positive.
The purpose of this experiment is to determine the absolute configuration of an unknown chiral secondary alcohol using the competing enantioselective conversion (CEC) method. This method uses both R- and S- enantiomers of a chiral acyl-transfer catalyst called homobenzotetramisole (HBTM), in separate parallel reactions, and thin layer chromatography to identify the stereochemistry of the secondary alcohol, whether it be an R- or S- enantiomer. Quantitative analysis was performed using a program called ImageJ after the appropriate picture was taken of the stained TLC plate. The molecular structure of the unknown alcohol was identified using 1H NMR spectroscopy by matching the hydrogens to the corresponding peak.
MTT assay was used to analyze cell viability of MCF 10A, MCF 7 and MDB-MB 231 cell lines in control and 10mM inorganic phosphate treated groups. MTT assay is a colorimetric assay for evaluating cell metabolic activity. MTT (3-[4, 5-dimethylthiazol-2-yl]-2, 5-diphenyltetrazolium bromide) is a yellow aqueous tetrazolium dye. In living cells with active mitochondria, the mitochondrial enzymes such as succinate dehydrogenase (NADPH dependent oxidoreductase enzyme) reduce this dye to formazan, a purple-colored water-insoluble complex (Gomez et al., 1997). The intensity of absorption of the purple complex is read typically at 595nm using a spectrophotometer and is a direct measure of mitochondrial activity.
The product was recrystallized to purify it and the unknown filtrate and nucleophile was determined by taking the melting points and performing TLC. Nucleophilic substitution reactions have a nucleophile (electron pair donor) and an sp3 electrophile (electron pair acceptor) with an attached leaving group. This experiment was a Williamson ether synthesis usually SN2, with an alkoxide and an alkyl halide. Conditions are favored with a strong nucleophile, good leaving group, and a polar aprotic solvent.
Theoretical Values:. Methanol CH OH 17000 J/g. Ethanol C H OH 22000 J/g. Propanol C H OH 25000 J/g. Butanol C H