Thiocarbohydrazide Reaction Lab Report

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.

Experiment 55 consists of devising a separation and purification scheme for a three component mixture. The overall objective is to isolate in pure form two of the three compounds. This was done using extraction, solubility, crystallization and vacuum filtration. The experiment was carried out two times, both of which were successful.

In the Cannizaro reaction an aldehyde is simultaneously reduced into its primary alcohol form and also oxidized into it 's carboxylic acid form. The purpose of this experiment is to isolate, purify and identify compounds 1 and 2 which contain 4-chlorobenzaldehyde, methanol, and aqueous potassium hydroxide. Compounds 1 and 2 are purified by crystallization. . The purified product will be characterized by IR spectroscopy and melting point.

Abstract: One mixture of two unknown liquid compounds and one mixture of two unknown solid compounds were separated, isolated, purified, and characterized by boiling point. Two liquid unknowns were separated, isolated, and purified via simple distillation. Then, the process of an acid-base extraction and washing were used to separate two unknown compounds into two crude compounds: an organic acid and a neutral organic compound. Each crude compound was purified by recrystallization, resulting in a carboxylic acid (RCO2H) and a pure organic compound (RZ). The resulting mass of the pure carboxylic acid was 1.688g with a percent recovery of 31.80%, the boiling range was 244-245 °C, and its density was 2.0879g/mL. The resulting mass of the pure organic solid was 2.4902g with a percent recovery of 46.91%, the boiling range was 52.0-53.4°C, and its density was 1.5956 g/mL.

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.

Samples of benzophenone, malonic acid, and biphenyl were each tested with water, methyl alcohol, and hexane. Benzophenone was insoluble in water as it is nonpolar while water is highly polar. Benzophenone was soluble in methyl alcohol, dissolving in 15 seconds, because methyl alcohol is intermediately polar as benzophenone is nonpolar. Methyl alcohol is polar but not as much as water. Thus, the nonpolar benzophenone was soluble in methyl alcohol. Benzophenone was partially soluble in hexane because hexane is nonpolar as is benzophenone. Thus, benzophenone was dissolved in hexane. Malonic acid was soluble in water because both malonic acid and water are polar. It took 25 seconds for malonic acid to dissolve in water. Malonic acid was soluble in methyl alcohol because malonic acid is polar and methyl alcohol is intermediately polar, allowing malonic acid to dissolve in the methanol in 15 seconds. Malonic acid was insoluble in hexane because hexane is nonpolar while malonic acid is polar. Biphenyl was insoluble in water as water is highly polar whilst biphenyl is nonpolar. Biphenyl was partially soluble in methanol which is intermediately polar whilst biphenyl is nonpolar, allowing it to dissolve a little. Biphenyl was soluble in hexane because both biphenyl and hexane are nonpolar molecules. Biphenyl dissolved in hexane in 10 seconds.

After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some

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

Using SN1 reaction mechanism with hydrochloric acid, t-Pentyl alcohol was converted to t-Pentyl chloride in an acid catalyzed reaction. The reaction took place in a separatory funnel designed to separate immiscible liquids. The crude product was extracted by transferring a solute from one solvent to another. The process of washing the solutions by phase transfer was used in order to remove impurities from the main solvent layer. Finally, the crude product was dried with anhydrous Calcium chloride and purified once more by simple distillation technique.

1H Nuclear magnetic resonance (NMR) of hydrolysed products obtained by enzyme CtXynGH30 treatment of substrate beechwood xylan was performed using a spectrometer (Bruker, 600 MHz). The enzyme reaction was performed in 200 μl reaction mixture by taking 3.4 μg of CtXynGH30 and (1%, w/v) beechwood xylan dissolved in 20 mM sodium phosphate buffer, pH 6.0 and incubated for 1 h at 50°C. The protein and undigested polysaccharides were precipitated by adding equal volume of acetone (200 μl) with gentle mixing and subsequently centrifuged at 13000g for 5 min. The supernatant was lyophilized. The 10-15 mg of this lyophilized sample was dissolved in the 0.75 ml of D2O. The sample was placed in the NMR tube (0.5 mm, Sigma-Aldrich) and the spectra were

Once the distillate had been collected into two separate vials, both distillates were washed with aqueous sodium bicarbonate (1.5-ml, 5%). The aqueous layer (lower) was extracted from both vials using a pipette and put into a chemical waste bin. The organic (alkene) layer was then dried with anhydrous calcium chloride pellets (3 pellets per vial). Both distillates were analyzed using gas chromatography, and each peak shown was identified to be one of the alkenes. Analysis of the graph was used to determine the major and minor products of the reaction.

A pre-weighed (0.315g) mixture of Carboxylic acid, a phenol, and neutral substance was placed into a reaction tube (tube 1). tert-Butyl methyl ether (2ml) was added to the tube and the solid mixture was dissolved. Next, 1 ml of saturated NaHCO3 solution was added to the tube and the contents were mixed separating the contents into three layers. Once this was completed

The reaction is carried out in saturated aqueous ammonium chloride solution. Thus no special drying of solvents, reagents, or glassware is required. The reaction mechanism for this experiment can be seen below (Fig. 2)

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