Synthesis And Recrystallization Of Adipic Acid

The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.

Alcohol dehydrations are widely used in many industries to produce alkene. In this experiment 2-methylcyclohexanol was dehydrated to three possible products using phosphoric acid as a catalyst. The main tool for this experiment is the Hickman still. First, Drierite was added to the Hickman still so that any excess water formed during the experiment will be absorbed. It also acted as a boiling stone and addition surface to increase surface area. Next, 0.75 mL of 2-methylcyclohexanol is added to the still and right after 1 mL of phosphoric acid is added. The phosphoric acid (H3PO4) acts as a catalyst in order for the reaction to occur. The mixture is heated up to between 120o Celsius and 160o Celsius. If the temperature goes above 165oC then

The sodium hydroxide acts to pull the hydrogen off the oxygen in the 2-methylphenol so that the oxygen has a negative charge and can attack the sodium chloroacetate. Again, using a 1:1 molar ratio, 0.34 g (2.9 mmol) of sodium chloroacetate (the good leaving group) was added to 1 ml of water and dissolved. Following dissolving all of the 2-methylphenol (to avoid the sodium hydroxide reacting concurrently with the sodium chloroacetate and 2-methylphenol) in the sodium hydroxide, the aqueous solution of sodium chloroacetate was transferred to the reaction flask. This mixture was then heated to reflux, using a medicine dropper affixed to the top of the flask as an alternative method to boil without

We used TLC analysis to identify each product obtained from the dihydroxylation reactions by spotting a TLC plate with the product of our reaction, a solution of cis-cyclohexane, trans-cyclohexane, and a 50:50 mixture of the two. We then placed the plate in a beaker with ethyl acetate saturating the atmosphere to allow the TLC plate to develop. Finally, we compared Rf values of the components of the mobile phase, after the phase was completed. 100% ethyl acetate was used instead of 100% Hexane or a mixture of Ethyl Acetate, because ethyl acetate has high polarity and can separate the components of a mixture to elution, unlike hexane, which is non-polar, and therefore unable to separate the components of the mixture. A 50:50 mixture of both would not work, because the polar and non-polar compounds would neutralize the mixture, and thereby not separate the components of the mixture.

Abstract: Using hypochlorous acid to convert secondary alcohol called cyclododecanol to the corresponding ketone which is cyclododecanone by oxidation.

The crude product was washed by taking the reaction product in the separatory funnel and adding 23 mL of deionized H2O. The mixture was shaken and allowed to settle until layers were observable. The top layer was the desired product and approximately 25 mL of aqueous layer was extracted from the separatory funnel. Next, 25 mL of 5% NaHCO3 was added to the separatory funnel in order to neutralize the acid. This mixture was swirled, plugged with the stopper and inverted. Built-up gas was released by turning the stopcock to its opened and closed positions, releasing CO2 by-product. This was done four times in one minute intervals. The solution was allowed to settle until layers were observable. The bottom layer that contained salt, base and water was extracted from the separatory funnel. The crude product was washed again as mentioned previously.

The purpose of this lab was to carry out a dehydration reaction of 2-methylcyclohexanol by heating it in the presence of phosphoric acid and determining which alkene product would be the major product. Methylcyclohexanols were dehydrated in an 85% phosphoric acid mixture to yield the minor and major alkene product by elimination reaction, specifically E1. The alkenes were distilled to separate the major and minor products and gas chromatography was used to analyze the results and accuracy of the experiment. The hypothesis was the major product of the reaction would be the most substituted product. This conclusion was made because of

(1) AChE and BChE showed greatest activity when hydrolysing their native substrates; ACh and BCh respectively. AChE rapidly hydrolysed ACh, however it hydrolysed BCh at a minimal rate (0.83%). In contrast, BChE showed comparatively minimal difference in catalytic efficiency in the hydrolysis of ACh, upon which is concurrent with Radic et al (1993) (Figure1).

In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this

The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we

As the acid was being added, the mixture was being stirred over a stir plate. Once completed, the reaction mixture was poured from the round bottom flask into a 500 mL separatory funnel and its top (organic) layer was extracted into another beaker. The bottom (aqueous) layer was placed back into the funnel and extracted twice with 50.0 mL of ethyl ether each. The newly extracted layers were combined and dried over magnesium sulfate (MgSO4). The dried solution was the decanted into a beaker to remove the MgSO4 salts and the product solution was collected via Buchner vacuum filtration. The resulting product was transferred into an Erlenmeyer flask with an inverted beaker on top and stored in a drawer.

The purpose of the experiment is to oxidize a secondary alcohol (2-octanol) by using sodium hypochlorite (bleach) to produce 2-octanone. The starting material consisted of a sample of 2-octanol that was placed into a three-neck flask along with acetic acid and acetone creating an acidic solution. While monitoring temperature fluctuations to ensure a temperature of 400 Celsius was not reached, sodium hypochlorite slowly dripped from a separatory funnel into the acidic solution. Once this reaction reached its entirety, the solution was combined with sodium bisulfate to remove any of the remaining oxidizing agent. This solution was then tested and brought to a neutral pH using a sodium hydroxide solution. The reaction material was extracted using ether and was then washed with a saturated sodium chloride solution. The organic solution was then dried using magnesium sulfate and was then decanted and placed onto the rotovap. The produced weighed .599g and based on the infrared spectrum analysis (see Figure 1) preformed on the product it was determined to be 86.1% 2-octanol, which means .516g of 2-octanol was obtained in the final product.

This experiment was conducted in order to convert the reagents borneal to camphor, using chromic acid. The overall reaction is an oxidative one. Depending on the structure of the reacting alcohol molecule, an oxidized alcohol can yield aldehydes and carboxylic acids or ketones. Primary alcohol has the ability to yield aldehyde or carboxylic acid, while secondary alcohol possess the ability to yield ketone when they are oxidize. The oxidizing agent used in this experiment was chromium oxide with diluted sulfuric acid. This reagent can be prepared by mixing dichromate in a solution of water and sulfuric acid. Adding chromium trioxide to diluted sulfuric acid may yield chromic acid as well. A less active form of oxidizing agent can be produce

A 10 mL round-bottom flask was weighed both before and after approximately 1.5 mL of the given alcohol, 4-methyl-2-pentanol, was added. 3 mL of glacial acetic acid, one boiling chip, and 2-3 drops of concentrated sulfuric acid were added to the flask in that order. The reflux apparatus was assembled, the

1,7-octadiene yields cyclohexene and ethylene in a metathesis reaction through a ring closing mechanism (RCM). For the experiment, 1,7-octadiene was taken along with 1,1,8,8-tetradeutero-1,7-octadiene, that is, 1,7-octadiene with all the terminal hydrogens replaced with deuterium.