The alcohol starting material, 2-methylcyclohexanol, was dehydrated through an E1 elimination by using of phosphoric acid as a catalyst. After a purification by simple distillation, which removed the alkene product and the by-product water from the reaction mixture, the methylcyclohexene products were analyzed by percent yield, boiling point, IR spectroscopy, and two chemical tests, Br2 in CCl4 and Jones test. By performing the simple distillation using pyrolysis, 85% of phosphoric acid and 2-methylcyclohexanol were added into the boiling flask, where the product from the collecting flask was condensed by the ice, and washed with the saturated sodium chloride. The weight of the product was determined and the percent yield of the product was …show more content…
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 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
Solid triphenylmethanol (0.200 g, 0.768 mmol) and sulfuric acid (2 mL) were added to a reaction tube, which was then ground using a glass rod until it dissolved and turned a dark orange color. The mixture was then added dropwise via a glass pipette into another reaction tube containing methanol (1 mL). An extra amount of methanol (2 mL) was used to transfer the rest of the contents of the first reaction tube. Formation of crystals was facilitated by scratching the side of the tube and adding additional methanol until the color changed to an off-white color. The contents of the tube were then vacuum filtered with water and the resulting crude product was weighed and then recrystallized using hot methanol to form triphenylmethyl methyl ether (0.051 g, 0.186 mmol, 24.2%). The melting point was 81 – 83˚
A weak peak was at a position between 1600-1620 cm-1 can also be seem in the IR, which was likely to be aromatic C=C functional group that was from two benzene rings attached to alkynes. On the other hand, the IR spectrum of the experimental diphenylacetylene resulted in 4 peaks. The first peak was strong and broad at the position of 3359.26 cm-1, which was most likely to be OH bond. The OH bond appeared in the spectrum because of the residue left from ethanol that was used to clean the product at the end of recrystallization process. It might also be from the water that was trapped in the crystal since the solution was put in ice bath during the recrystallization process. The second peak was weak, but sharp. It was at the position of 3062.93 cm-1, which indicated that C-H (sp2) was presence in the compound. The group was likely from the C-H bonds in the benzene ring attached to the alkyne. The remaining peaks were weak and at positions of 1637.48 and 1599.15 cm-1, respectively. This showed that the compound had aromatic C=C function groups, which was from the benzene rings. Overall, by looking at the functional groups presented in the compound, one can assume that the compound consisted of diphenylacetelene and ethanol or
In this experiment, column chromatography and thin layer chromatography were used to separate a mixture of fluorene and 9-fluorenone. These two methods were then compared, and the results were analyzed. In column chromatography, 0.1010 g of mixture was separated. During the separation, fluorene eluted first. This compound was white in color once dried with the rotary evaporator. A percent yield of 93.47% was calculated for fluorene. The product that eluted first was confirmed to be fluorene by the IR spectrum obtained and the experimental melting point. The IR spectrum RM-02-CC1 was the spectrum obtained for this compound. Aromatic carbon- hydrogen bonds, carbon-carbon double bonds and hydrogens attached to sp2 carbons were shown by peaks 3038
As a result, the laboratory experiment was determined to be successful and the two product samples obtained and completed calculations displayed that overall bromide was a stronger nucleophile as the chloride ion was more electronegative than bromide, which allowed it to hold electrons in closerE. In conclusion, since bromide is less electronegative and has more electrons, it was able to share the unpaired electrons more easily than chlorideA. These results were expected, as the alkyl bromide would be the major product of procedure A as it followed the SN2 mechanism which was based on nucleophile strength and the product from procedure B would be a near-equal mixture as it followed the SN1 reaction mechanismC. The methods used during this experiment allowed for a successful completion and determination of the better nucleophile, but other additions and observations would have been interesting and beneficial as well. A possible examination of the two sample products collected using pH tested values or observation of sample spotted chromatography paper under a
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 percentage yield gained was 70% from the Fischer Esterification reaction, which evaluates to be a good production of yield produced as the reaction is known to be reversible where conditions such as the concentration of the reactants, pressure and temperature could affect the extent of the reaction from performing. These white crystalline crystals were tested for impurity by conducting a melting point analysis and taking spectrospic data such as the IR spectra, HNMR and CNMR to confirm the identification of the product. These spectrospic methods and melting point analysis confirmed the white crystalline crystals were benzocaine.
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.
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.
In a small reaction tube, the tetraphenylcyclopentadienone (0.110 g, 0.28 mmol) was added into the dimethyl acetylene dicarboxylate (0.1 mL) and nitrobenzene (1 mL) along with a boiling stick. The color of the mixed solution was purple. The solution was then heated to reflux until it turned into a tan color. After the color change has occurred, ethanol (3 mL) was stirred into the small reaction tube. After that, the small reaction tube was placed in an ice bath until the solid was formed at the bottom of the tube. Then, the solution with the precipitate was filtered through vacuum filtration and washed with ethanol. The precipitate then was dried and weighed. The final product was dimethyl tertraphenylpthalate (0.086 g, 0.172mmol, 61.42%).
Forsyth, D., Lapid, M., Ellenbecker, S., Smith, L., O'Neil, M., Low, D., Clobes, J., Drier, J., & Seifers, M. (2008). Hydration status of geriatric patients in a psychiatric hospital. Issues in Mental Health Nursing, 29(8), 853-862.
With all three TLC plates, with varying quantities of hexane and hexane: ethyl acetate, the unknown and the 4- Methoxy-phenol moved the same distance up the plate towards the solvent front. The substitution reaction was successful and lead to the formation of a methoxybenzyl phenol ether with the 4- Methoxy-phenol nucleophile. The data taken from the TLC and the melting points confirmed
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
Methanol was the most polar among 3 alcohols used in this part, hence was soluble in water as both water and methanol were polar. However, methanol was partially soluble in hexane because the Van der Waals interaction between methanol
The mixture of bio-oil (40 g) and ethanol (10 g) was placed with amberlyst 36 resin into the autoclave reactor (200 mL SUS316). The reactor was sealed and flushed three times with N2. After that, the reaction was performed at under mild temperature conditions (50, 100, or 150 °C) under 3 MPa H2 pressure. After the resin