3 5 Trimethylcyclohexanone Lab Report

Measure the initial width, length, and thickness of the steel specimen using a Dial Caliper. Relieve pressure in Amatrol T9014 and adjust the height of the bottom platform to insert steel specimen. Insert one pin into the bottom platform to hold the steel specimen into the fixture. Slide two locking bars down the steel specimen. Adhere one locking bar to the bottom of the specimen and one at the top, lock them in place using the attached thumb screws. Insert the Linear Vernier Caliper in the top locking bar and zero out the caliper, allowing it to rest on the bottom locking bar. Compress the hydraulic cylinder until the indicator reads a force of zero. Lock the Linear Vernier Caliper in place by tightening the top thumb screw. [1] Compress

b) Iron and Barium were present in unknown 3. Assigned unknown reacted with all 4 reactants and formed precipitate with 3 of them (Sodium carbonate, sodium hydroxide and Sulfuric acid). During the experiment it reacted very similarly to Iron (III) nitrate and Barium nitrate. For example, with it was tested against Ammonium Chloride, the color of the solution changed to a light green, very identically to Iron (III) nitrate and Ammonium Chloride. Besides, unknown 3 formed an orange brownish precipitate when it was tested with sodium carbonate. Iron (III) nitrate acted similarly. Moreover, unknown 3 reacted similar to Barium nitrate when it was tested against ammonium chloride and sulfuric acid. It did not form any precipitate with ammonium chloride but formed a very light white precipitate, which is identical to barium nitrate’s reaction against sulfuric acid. Therefore, the two present metal in unknown 3 are Iron and barium.

Objective The objective of this experiment is to prepare a sample of tetraphenylcyclopentadienone through the aldol condensation of benzil and dibenzyl ketone under a basic environment. Procedure Part A- Aldol Condensation of Tetraphenylcyclopentadienone • In a 100 mL round bottom flask, 0.525 g (0.0025 mol) of benzil and 0.525 g (0.0025 mol) of dibenzyl ketone were mixed with an additional 0.075 g (0.002 mol) of potassium hydroxide pellets in a solution of 10 mL of 95% ethanol, and finally a boiling chip was inserted into the solution. The contents of the mixture were allowed to mix, and while this was occurring, a reflux setup was prepared (as illustrated in Figure 1.A) and the round bottom flask was attached to the setup.

Substance one was determined to be iron because it was magnetic, and the its melting point was 1535℃, its boiling point was 3000℃, and its density was 1870 g/L. Substance 2 was determined to be wood, because it was lightweight and grainy and a wooden color. It also floated, meaning it had a density less than water, like wood. Substance 3 was determined to be sand, because it was small rocks, which is sand, and had a melting point of 1610℃, a boiling point of 2230℃, and a density of 2650 g/L. Substance 4 was determined to be salt, because it was made of small, white grains, and conducted electricity. It had a melting point of 801℃, a boiling point of 1413℃, and a density of 2170 g/L. In this lab, physical interactions were used to determine

Methylene chloride is added to the flask with the diester. The seperatory funnel is attached to the flask with 1.0 M bromine inside. Bromine is added to ester mixture drop by drop until the solution stays a yellow color. After ten minutes a cyclohexene and methylene chloride mixture is added drop by drop to remove the excess bromine. Ester solution is placed on the rotary evaporator at 45°C. Ethanol was added to the product. Solution was cooled in an ice bath for thirty minutes and crystals began to form. Solution was vacuum filtered with a Hirsch funnel. The mass of the product was 0.47 g. MP 70.1-75.3°C The theoretical yield was .74 g. This makes the percent yield 64%. The expected melting point was 123-125°C. The diacid was not the product formed. With IR, HNMR, and CNMR data the identity of the final product was found. IR (neat) 2989.8 and 2955.7 (Sp3 C-H), 1785.8 (Lactone ester), 1735.8 (ester). 1H NMR (CDCL3) 5.073 ppm (d, 1H), 4.991 ppm (d, 1H), 4.637 ppm (d, 1H), 4.599 ppm (d, 1H), 3.764 ppm (s, 3H), 3.364 ppm ( m, 1H), 3.130 ppm (m,1H), 2.948 ppm (d, 1H), 2.558 ppm (m, 2H), 2.363 ppm ( m, 1H), 1.934 ppm (s, 1H), 1.728 ppm (s, 1H). 13C NMR (CDCL3) 177.037 ppm, 171.388 ppm, 88.171 ppm, 53.125 ppm, 50.270 ppm, 49.297 ppm, 49.328 ppm, 49.040 ppm, 41.317 ppm, 36.441

The main purpose of this experiment is to synthesize, isolate, extract and characterize 4-methylcyclohexe. The reaction is performed by performing a combined reflux and distillation procedure on the reactant 4- methylcyclohexanol along with catalysts concentrated sulfuric and phosphoric acid combined with heat. The combination of reflux and distillation procedure prevents the backward reaction through the formation of water. The reflux reaction is especially useful as the addition of heat during this process allows for an increase in the fraction of useful collisions. This allows the reaction to proceed faster.

The percent recovery was calculated by finding the moles of the initial and final products. The moles of the initial product were found by multiplying the volume used by the density of 2-methyl-2-butanol, and then dividing by the molar mass. The percent recovery was good, showing few errors were made and that the lab went as expected. To improve the recovery, the extractions could be done even more carefully.

Overall, the experiment went smoothly. Our product’s identity and purity was tested by calculating the density, an alkene test using Bromine Water, and conducting both an IR and a H-NMR spectra. The first test that was conducted was comparing densities between our product and the known density of Limonene. From our data, our product had a density of 0.815 g/mL, which is only 0.027 g/mL off from Limonene’s known density of 0.842 g/mL. Our density may even be closer due to the inaccuracy of having less than one millimeter of product.

Dehydration of 2-methylcyclohexanol to 3-methylcyclohexene is simple distillation where dehydration was used to prepare the final product. The results of the experiment showed that the 3-methylcyclohexene was formed via an E1 reaction from 2-methylcyclohexanol with a 1:1 ratio of sulfuric acid and phosphoric acid. However, some H2O was left over, which was seen when we look at the IR and see a small water peak. This could be due to the fact that not enough sodium sulfate was added and not for long enough. These results were confirmed by the quality tests that showed that a precipitate formed when KMnO4 was added to the solution and in the IR spectroscopy peaks showed peaks at 3022.62cm-1 which matches an alkene, further showing that the formation of 3-methylcyclohexene was successful with a percent yield of 56.46%.

Three types of reaction were conducted, unimolecular nucleophilic substitution reaction (SN1), unimolecular elimination reaction (E1), and bimolecular nucleophilic substitution reaction (SN2). Substitution and elimination reactions are important to allow for the transformation of reactants to desired product. This is extremely important when it comes to synthesis of different molecules for research, commercial, and medical purposes. SN1reaction was to create 2-chloro-2-methylbutane from 2-methyl-2-butanol with a reaction yield of 2.28 g (21.4 mmol) and the reaction product was analyzed by infrared spectroscopy (IR) to determine the purity of 2-chloro-2-mehtlybutane. E1 was to create cyclohexene from cyclohexanol with a reaction yield of 0.17

The H-NMR of the unknown alcohol was provided for analysis in order to determine the identity. Based on the peaks and their respective locations, the unknown was determined to be isopentanol. The peak at 0 ppm was the TMS. From this, the first doublet peak represented the six hydrogens located on the two terminal carbons, the signal was split as a result of the single hydrogen from the adjacent carbon. This peaks falls within the typical range for a primary alkyl hydrogen, 0.7-1.3 ppm. The next peak is a quartet that has a

To a solution of o-aminoester 1 (0.9 g, 3 mmol) in DMSO (5 mL), carbondisulfide (0.3 mL), saturated sodium hydroxide (0.2 mL) and dimethyl sulfate (0.5 mL) were added. The mixture was stirred overnight (TLC showed complete conversion). The precipitate that formed was filtered off, washed with ethanol and crystallized from methanol to give compound 3 as yellow crystals (0.72 g, 62%); mp: 168-169oC; 1H-NMR (400 MHz, DMSO-d6): δ 1.21 (t, 3H, J ¬= 7.1 Hz, COOCH¬2¬CH-3), 1.32 (t, 3H, COOCH¬2¬CH¬3), 2.80 (s, 3H, CH¬3), 2.82 (t, 2H, J ¬= 6.5 Hz, H-4), 3.62 (t, 2H, J¬ = 6.5 Hz, H-5), 4.03 (q, 2H, J = 7.2 Hz, COOCH¬2¬CH¬3), 4.08 (bs, 1H, NH), 4.30 (s, 2H, H-7), 4.53 (q, 2H, J = 7.2 Hz, COOCH¬2¬CH¬3); 13C-NMR (100 MHz, DMSO-d6): δ 14.2 (CH3), 22.8 (C-4),

The experimental value of the maximum wavelength for 1-1’-diethyl-2-2’-cyanine iodide was 525nm and the calculated value when p=0nm is 141nm, which shows that 0nm is too small. To get a penetration distance for the dye Equation 4 was used and the value was 0.2439nm. This value of p is much larger than the original guess made for the penetration distance is the pre-lab. Using the calculated penetration distance from this dye, the wavelength of pinacyanol chloride is calculated to be 654nm. This value is about 50nm off the experimental value, which at this scale is significance. A penetration distance was found for pinacyanol chloride, using its experimental maximum wavelength, giving a value of 0.207nm. Using this value to solve for the

Cyclohexanol, secondary alcohol, undergoes dehydration by an E1 mechanism. To prepare a cyclohexene, it is essential to restrain the substitution reaction. In this experiment, the substitution reaction is completed by the use of strong acids with anions that are mostly poor nucleophiles, a high reaction temperature, and distillation of cyclohexene from the reaction mixture as it is formed. The side products of this reaction are similar to those that are encountered in the preparation of n-pentyl bromide, the only difference is that the alkene is no longer a side product but is now the desired product. The dehydration of Cyclohexanol is carried out in a way that the product Cyclohexene is distilled from the reaction mixture. The distillation

This experiment provided accurate data of how a mixture of solids, and liquids consisting of both nonpolar and polar substances can be separated using vacuum filtration and water. The separation of oil from the sand, KNO3, and CuSO4 mixture using ethyl acetate was performed using a vacuum filtration. Ethyl acetate is an ester of ethanol and acetic acid with a formula of CH3-COO-CH2-CH3 (Tro, 975). Ethyl acetate is a suitable solvent due to its ability to undergo hydrolysis. Hydrolysis is the breaking apart of chemical bonds with the addition of water. Both oil and ethyl acetate are nonpolar in nature, whereas sand, CuSO4 and KNO3, are polar in nature. This separation of polarity allows for a natural separation of the substances to occur. Nonpolar