4-Tert-Butylcyclohexanone Lab Report

In recent years, there is an increasing demand of flavoured compounds in industry sectors, especially food and beverage, cosmetic and pharmaceutical industries 1–4. These compounds are generally short chain ethyl esters which are characterized by their strong fruity flavour and fragrance. Ethyl hexanoate is such a short chain acid ester which gives an apple-pineapple flavour 5,6. Most of the flavours are extracted from their natural source, but this process can take a long time and rigorous efforts eventually ending up with an inefficient yield. There are numerous ways for the synthesis of organic esters and most of which have been briefly studied by Yadav and Mehta 7. The simple and old route for preparing esters is by the reaction

After the assigned reaction was complete, samples of authentic cis-cyclohexene-1,2-diol, authentic trans-cyclohexene-1,2-diol, a 50:50 mix of the cis and trans cyclohexene-1,2-diols, and the product were each spotted on the Thin Layer Chromatography (TLC) plate. Then the TLC plate was placed inside a saturated beaker filled ethyl acetate in order to develop the plate. Once the solvent traveled up the solvent front, the plate was stained with anisaldehyde solution and then heated with a heat gun so the results could be visible. When looking at the results, the spot for the authentic cis-cyclohexene-1,2-diol turned a dark purple/light pink color, the spot for the authentic trans-cyclohexene-1,2-diol turned a light purple/blue color, the spot of the 50:50 mix of the cis and trans cyclohexene-1,2-diols turned a dark purple/light pink color, and the spot for the product turned a dark pink color. The color similarities between the product, the cis-cyclohexene-1,2-diol, and even the 50:50 mix of cis and trans diols indicated that the

The purpose of this lab is to examine the composition of three components of gas products of elimination reaction under acidic condition by conducting the dehydration of primary and secondary alcohol, and under basic condition by conducting the base-induced dehydrobromination of 1-bromobutane and 2-bromobutane. Then gas chromatography is used to analyze the composition of the product mixtures.

To perform the test, obtain a clean wooden splint. Soak the splint in DI water for at least 10 minutes. Remove the splint from DI water and shake off the excess. Place the splint in your test solution for 1-2 minutes.

The purpose of this experiment was to perform a bromination reaction that converts cyclohexane to trans-1,2-dibromocyclohexane. To do this, 1 mL of 30% hydrogen peroxide was mixed with 3 mL of bromic acid in a round bottom flask containing a spin vane. The solution turned from clear to orange, dark red. The color change is a useful indicator to identified whether reaction was completed before moving to another step. Next, 1 mL of cyclohexene was pipet into this mixture, which changed the solution from red to orange and eventually yellow. The mixture was transferred into a centrifuge tube with brine solution. Two layers were formed, with a yellow layer on top and the clear bottom layer. The bottom layer is the only organic layer because it is denser. NaHSO3 was used to washed the mixture. The bottom layer was extracted by pipette and rinsed with NaSO4 for drying. The organic layer was transfer into a vial and placed under NEVEP to attain a solid product. The product was a mixture of white solids with liquid.

This experiment converted cyclohexanol into cyclohexene by means of elimination reaction with the addition of 85% phosphoric acid. In comparison, the product obtained was a clear colorless liquid with a strong odor similar to the original solution. However, when combined together in the seperatory funnel there was two distinct layers formed. This is evident that a reaction took place and the product formed is a different compound than the original. In order to confirm that a different product was formed, additional test were performed to solidify the characterization. Test such as Bromination, IR spectroscopy, refractive index, and measures physical properties confirmed that the product collected was the desired product, cyclohexene.

The isolation and purity of crude acetylferrocene were tested through column chromatography. Crude acetylferrocene was observed to be an orange powder with a mass of 2.28 g. The percent yield was 124% ((2.28g/1.84g) x100%). The high percent yield was due to the high amount of sodium bicarbonate added in the previous lab. .100 g was weighed out on an evaporation dish. 6.00 g of silica gel was obtained in an Erlenmeyer flask. The solvent used was 100 mL of 80:20 petroleum ether/ethyl acetate. The silica gel and solvent were slurred together and poured quickly into the column through a funnel. The slurry was white and cloudy. The slurry was packed and made two layers: silica gel as the bottom layer while the clear solvent as the top layer. 5 mm of sand was added and resided on the top of the silica gel layer.

Cyclohexanone a cyclic ketone was oxidized to adipic acid using the oxidizing agents concentrated nitric acid. Then, the recrystallized product was characterize by using infrared spectroscopy and taking the melting points. The experiment yielded 0.199 grams of adipic acid and a very high percent yield of 106.40%. Upon examination of IR-spectrum, Adipic acid was identified by comparing it to the IR-spectrums provided in the lab book. Furthermore, the melting point of the experiment was obtained to be 151-154 ºC, which included the theoretical melting point of 153 ºC between the experimental melting point range.

Crago, Kathleen. et. al,. Organic Chemistry Laboratory Manual, 7th Edition, Eiley, New York, pp 96-99

This experiment was started to measure the height equivalent of a HETP column to calculate twenty theoretical plates. The company need this information to separate the cyclohexane from the toluene. The separation was accomplished by the use of fractional distillation and gas chromatography. The process yielded one plate for the17.6cm column meaning, that the porcelain beryl saddles as a packing material are ineffective. Although the results were found to be inefficient this may have been due to an error in the calculation, or the amount of time per temperature spent collecting the fractions. These results can be improved by re-distillation of the distillate fraction.

The purpose of this experiment was to identify the unknown alkyl bromide and ketone using a Grignard reaction and IR spectrum. Also, retrosynthesis analysis was used to determine the success of identifying starting material. The organometallic compounds have a carbon-metal bond that is used to create alcohol and to expand chains of carbons. Grignard reagents, a part of organometallic ionic compounds, are widely used in organic synthesis because they are considered strong base, strong base carbon nucleophile, and soluble in many organic solvents.

Based on the results, it is determined that the cyclohexane and ethyl acetate produce a positive deviation and chloroform and acetone create a negative deviation together. The cyclohexane and the ethyl acetate were unable to form any intermolecular bonds with each other, which created the low boiling points and the low azeotrope. The two compounds would rather stay in a pure status than be mixed together. The chloroform and the acetone created hydrogen bonding with each other, which increased the intermolecular forces. This caused the mixture to have high boiling points than the two pure liquids by themselves and create a high azeotrope.

The reaction scheme for the oxidation of cyclohexene to adipic acid is shown in Figure 2. This reaction was an ionic addition reaction, and it utilized the oxidizing properties of H2O2 in the presence of WO42-. For this reaction to occur, first Na2WO4 dissociated in the aqueous layer due to its ionic properties and the polarity of water as the solvent. WO42-, a complex stabilized by its resonance contributors, was taken into the organic layer by Aliquat 336, the phase transfer catalyst. Aliquat 336 was originally in an ionic form with Cl- as the anion, but the chlorine was transferred to the aqueous layer as the phase transfer took place. Aliquat 336 is a good phase transfer catalyst due to its molecular structure. It contains a nitrogen that bears a positive charge as well as 3 long, hydrocarbon

Experiment 3 comprised three reactions: formation of dimethyl tetraphenylphthalate, hexaphenylbenzene, and tetraphenylnaphthalene. All 3 reactions used tetraphenylcyclopentadienone as the diene to generate products with high aromatic stabilization.

The purpose of this experiment is to perform a Friedel-Crafts reaction of ferrocene. Friedel-Crafts reactions are examples of electrophilic aromatic substitution reactions in which the electrophile is a carbocation or an acylium ion. These reactions form a carbon-carbon bond and allows for either an alkyl or acyl group to be substituted onto an aromatic ring. Figure 1 shows the general mechanism for the Friedel-Crafts acylation of benzene. First, the alkyl halide reacts with a strong Lewis Acid catalyst, usually aluminum chloride, to form a complex, which will then lose the halide to the Lewis acid to give the electrophilic acylium ion. The ion, stabilized by resonance, will react with the p-electrons from a double bond in benzene (acting as a nucleophile) and form the cyclohexadienyl cation intermediate and the tetrachloroaluminate anion. The anion then acts as a base to remove a proton from the ring and reform the initial Lewis acid. The ring regains its aromaticity and the product, an aromatic ring with an acyl substituent is fully synthesized.