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 …show more content…
Camphor extracted into dichloromethane because it is mostly organic from its heavy presence of hydrocarbons and this organic layer remained at the bottom of each extraction because of the weight that the halogen atom chlorine bares. Sodium bicarbonate was used to neutralize the pH. Sodium bisulfite solution was used to catch any redox reactions. The Anhydrous sodium sulfate was used to pull out any remaining water and the solution was gravity filtered and vacuum filtrated to yield dry camphor. The dry camphor had a melting point of 177.1-177.9°C, which is a little high. The explanation can be found in having packed too much of the product in the melting point capillary, where a little more heat may have been …show more content…
Oxidation allowed for borneol to be oxidized into camphor using the oxidizing agent hypochlorous acid. Reduction allowed for camphor to be reduced into two possible products, borneol and isoborneol, using sodium borohydride. The stereochemistry of the two possible products was distinguished on the NMR spectrum by the way that the hydride ion added in. As diastereomers, these products will have different properties noticeable in polarimetry, melting point, and even other techniques such as gas chromatography. All in all, Isoborneol was the major product because there were more moles of it formed, as evident by the integration values on the NMR
In the lab, Inhibiting the Action of Catechol Oxidase we had to investigate what type of enzyme inhibition occurs when an inhibitor is added. Catechol oxidase is an enzyme in plants that creates benzoquinone.Benzoquinone is a substance that is toxic to bacteria. It is brown and is the reason fruit turns brown. Now, there are two types of inhibitors, the competitive inhibitor and non-competitive inhibitor. For an enzyme reaction to occur a substrate has to bind or fit into the active site of the enzyme. In competitive inhibition there is a substrate and an inhibitor present, both compete to bind to the active site. If the competitive inhibitor binds to the active site it stops the reaction. A noncompetitive inhibitor binds to another region
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
Every 5 minutes, a small amount of mixture was dissolved in acetone (0.5 mL) and was spotted onto a thin layer chromatography (TLC) plate, which contained an eluent mixture of ethyl acetate (2 mL) and hexanes (8 mL). The bezaldehyde disappearance was monitored under an ultraviolet (UV) light. Water (10 mL) was added after the reaction was complete, and vacuum filtrated with a Buchner funnel. Cold ethanol (5 mL) was added drop-by-drop to the dried solid and stirred at room temperature for about 10 minutes. Then, the solution was removed from the stirrer and place in an ice bath until recrystallization. The recrystallized product was dried under vacuum filtration and the 0.057 g (0.22 mmol, 43%) product was analyzed via FTIR and 1H NMR
The experimental Fischer esterification of 8.92g of acetic acid with 5.0g of isopentyl alcohol using concentrated sulfuric acid as a catalyst yielded 4.83g (65.3% yield) of isopentyl acetate. The product being isopentyl acetate was confirmed when the boiling point during distillation had similar characteristics to that of the literature boiling points2. Physical characteristics like color and smell also concluded a match of our product with what was intended. 1H-NMR spectroscopy analysis supported this claim due to the fact that the integration values and chemical shifts were comparable to isopentyl acetate. Lastly, infrared spectroscopy (IR) showed similar key characteristics of our product’s wavelengths to that of pure isopentyl acetate5.
The boiling point of the product was conducted with the silicone oil. Lastly, for each chemical test, three test tubes were prepared with 2-methylcyclohexanol, the product, and 1-decene in each test tube, and a drop of the reagent were added to test tubes. The percent yield was calculated to be 74.8% with 12.6g of the product obtained. This result showed that most of 2-methylcyclohexanol was successfully dehydrated and produced the product. The loss of the product could be due to the incomplete reaction or distillation and through washing and extraction of the product. The boiling point range resulted as 112oC to 118oC. This boiling point range revealed that it is acceptable because the literature boiling point range included possible products, which are 1-methylcyclohexene, 3-methylcyclohexene, and methylenecyclohexane, are 110 to 111oC, 104oC, and 102 to 103 oC. For the results of IR spectroscopy, 2-methylcyclocahnol showed peaks at 3300 cm-1 and 2930 cm-1, which indicated the presence of alcohol and alkane functional group. Then, the peak from the product showed the same peak at 2930 cm-1 but the absence of the other peak, which indicated the absence of the alcohol
The purpose of this experiment was to see if phenylthiourea (PTU) is a non-competitive or competitive inhibitor. Catechol, a phenolic compound found in the potato extract used will play the part of the substrate. Competitive inhibitors are known to bind to the active site of an enzyme and mimic the job of a substrate. This in turn causes the substrate to compete for a position at the active site and increase the concentration of substrate but the inhibitor is still at a constant level. If PTU were a competitive inhibitor the test tube carrying the extract would turn dark brown. Non- competitive inhibitors are known to bind on the enzyme and prevent the substrate from attaching
In this lab 4-tert-butylcyclohexanone is reduced by sodium borohydride (NaBH4) to produce the cis and trans isomers of 4-tert-butylcyclohexanol. Since the starting material is a ketone, NaBH4 is strong enough to perform a reduction and lithium aluminum hydride is not needed. NaBH4 can attack the carbonyl group at an equatorial (cis) or axial (trans) position, making this reaction stereoselective. After the ketone is reduced by the metal-hydride, hydrochloric acid adds a proton to the negatively charged oxygen to make a hydroxyl group. The trans isomer is more abundant than the cis based on the results found in the experiment and the fact that the trans isomer is more stable; due to having the largest functional groups in equatorial positions.
Purpose/Introduction: In this experiment, four elimination reactions were compared and contrasted under acidic (H2SO4) and basic (KOC(CO3)3) conditions. Acid-catalyzed dehydration was done on 2-butanol and 1-butanol; a 2o and 1o alcohol, respectively. The base-induced dehydrobromination was performed on 2-bromobutane and 1-bromobutane isomeric halides. The stereochemistry and regiochemistry of the four reactions were analyzed by gas chromatography (GC) to determine product distribution (assuming that the amount of each product in the gas mixture is proportional to the area under its complementary GC peak).
The goal of this experiment is to determine which products are formed from elimination reactions that occur in the dehydration of an alcohol under acidic and basic conditions. The process utilized is the acid-catalyzed dehydration of a secondary and primary alcohol, 1-butanol and 2-butanol, and the base-induced dehydrobromination of a secondary and primary bromide, 1-bromobutane and 2-bromobutane. The different products formed form each of these reactions will be analyzed using gas chromatography, which helps understand stereochemistry and regioselectivity of each product formed.
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.
Enantiomers, a type of isomer, are non-superimposable, mirror images of each other. Diasteriomers, another type of isomer, are non-superimposable, non-mirror images of each other. Dimethyl maleate and dimethyl fumarate are diasteriomers, as they are not mirror images but instead vary in the orientation of the carbomethoxy groups around the double bond. Dimethyl maleate is the cis-isomer because both groups are on the same side and dimethyl fumarate is the trans-isomer because the two groups are on opposite sides. A bromine free radical mechanism was required for this conversion. First, energy from light is required to create two bromine free radicals from Br2. Then one of the free radicals attacks the double bond in dimethyl maleate, breaking it and creating a carbon radical on the other carbon. The bond then rotates and reforms, freeing the bromine radical and creating the trans-isomer, dimethyl fumarate. Bromine in this reaction is acting as a catalyst in this reaction and then cyclohexane is added at the end to neutralize the bromine free radicals. The activation reaction of the radical reaction is lower than the activation energy of the addition reaction, which is why it occurred more quickly. This reaction was successful because the percent yield was 67.1%, which is greater that 65%. It also demonstrated the expected principles, as the reaction did not occur without the presence of both light and bromine. The dimethyl fumarate had a measured boiling point of 100C to 103C, which is extremely close to the expected boiling point of 102C to
The solvent should be easily removed from the purified product, not react with the target substances, and should only dissolve the target substance near it’s boiling point, but none at freezing. A successful recrystallization uses minimum amount of solvent, and cools the solution slowly, if done to fast, many impurities will be left in the crystals. Using the correct solvent, in this case ice water and ethyl acetate, the impurities in the compound can be dissolved to obtain just the pure compound. A mixed solvent was used to control the solubility of the product. The product is soluble in ethanol an insoluble in water. Adding water reduced solubility and saturates the solution and then the crystals
Performing this experiment, we used the technique called Acid-Base extraction to isolate Eugenol, which is one of the main ingredients of clove oil. Acid-Base extraction is the most efficient method for isolating organic component; it is efficient because it purifies the acid and base mixture based on their chemical identities. We have seen throughout this experiment that acid and base play an important role, when it comes to solubility in water. Our basic knowledge of acid and base is acid is a proton donor and base is a proton acceptor. This ideology helps us to understand why organic compounds are not soluble in water. When compounds tend to be insoluble, we have to use acid and base reaction, to change its solubility. The changes that occurred