3-Butanediol Was Treated With Aqueous Sulfuric 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.

Discussion: In the synthesis of 1-bromobutane alcohol is a poor leaving group; this problem is fixed by converting the OH group into H2O, which is a better leaving group. Depending on the structure of the alcohol it may undergo SN1 or SN2. Primary alky halides undergo SN2 reactions. 1- bromobutane is a primary alkyl halide, and may be synthesized by the acid-mediated reaction of a 1-butonaol with a bromide ion as a nucleophile. The proposed mechanism involves the initial formation of HBr in situ, the protonation of the alcohol by HBr, and the nucleophilic displacement by Br- to give the 1-bromobutane. In the reaction once the salts are dissolved and the mixture is gently heated with a reflux a noticeable reaction occurs with the development of two layers. When the distillation was clear the head temperature was around 115oC because the increased boiling point is caused by co-distillation of sulfuric acid and hydrobromic acid with water. When transferring allof the crude 1-bromobutane without the drying agent,

In the controlled oxidation reactions of 1-butanol and 2-butanol with KMnO4, there is also a formation of water. The primary alcohol 1-butanol, reacted with KMnO4 to create butanal, an aldehyde, and water as products. Also the secondary alcohol, 2-butanol and KMnO4

The purpose of this experiment was to synthesize the Grignard reagent, phenyl magnesium bromide, and then use the manufactured Grignard reagent to synthesize the alcohol, triphenylmethanol, by reacting with benzophenone and protonation by H3O+. The triphenylmethanol was purified by recrystallization. The melting point, Infrared Spectroscopy, 13C NMR, and 1H NMR were used to characterize and confirm the recrystallized substance was triphenylmethanol.

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.

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

The purpose of this experiment was to synthesize t-pentyl chloride from the reaction of t-pentyl alcohol and concentrated HCl. This reaction occurred through an SN1 reaction, a unimolecular nucleophilic substitution reaction. This was a First Order Rate Reaction where the rate of t-pentyl chloride was dependent only on the concentration of t-pentyl alcohol. After the reaction was completed, the products were achieved via 3 liquid-liquid extractions and then after by simple distillation. In the liquid- liquid extractions a solute was transferred from one solvent to another. Then in the simple distillation the miscible liquids or the solution, was separated by differences in boiling points. After this the product was determined through infrared spectroscopy.

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.

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.

The solution that was performed in this experiment was to use sulfuric acid in order to form a protonated alcohol, so when the halogen or nucleophile back attacks the compound, water is displaced. Once the alcohol is protonated, the solution reacts in either an SN1 or SN2 mechanism.

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 dehydration of 2-methyl-2-butanol was performed using sulfuric acid and phosphoric acid in order to synthesize alkene products 2-methyl-1-butene and 2-methyl-2-butene. After carrying out steam distillation to isolate the organic alkenes from aqueous components within the reaction mixture, the purity and characterization of the products were then assessed through various analytical methods including Gas Chromatography (GC), Infrared Radiation (IR) Spectroscopy, and Nuclear Magnetic Resonance (NMR) Imaging. Through the characterization of the final products, it was found that little impurities remained in the final reaction solution and according to the GC, no alcohol remained in the vial after the reaction was complete. The actual yield

The objective of this lab was to synthesize an unknown ester using Fischer etherification, which involved using a carboxylic acid and an unknown alcohol as the reactants, and sulfuric acid as a catalyst. First, a reaction mixture was created using the reactants. Then the reaction product was isolated by removing the aqueous layer. After isolation, the crude ester product was purified using distillation. The final product was a clear liquid with a banana like odor. It was established that the banana like odor was coming from banana oil that is either pure isoamyl acetate or amyl (pentyl acetate). To identify the unknown ester IR, 13C NMR, and 1H NMR was obtained. IR spectroscopy, which showed prominent, peaks at 1737.54 cm-1, 1366.50 cm-1, 1228.27

Micromolecules in bio-oil, and pretreated bio-oil were identified from the GC/MS analysis and classified based on their chemical structure and functional groups. Their relative amounts are presented in Table 4. Total amounts of micromolecules were reduced after the pretreatment, despite the high yield of liquid product. Therefore, it might be due to the dilution with ethanol. Also, the distribution also strikingly changed during this reaction. Almost of acetic acid, and levoglucosan, which are known as decline bio-oil stability and properties, were changed into the ester form with ethanol, such as acetic acid ethyl ester, and levulinic acid ethyl ester. The compound like 2,2-diethoxy ethanol was only identified in the pretreated bio-oil, so it might be resulted from the reaction of ethanol itself. Since amberlyst 36 also has a capacity to phenol purification, total micromolecular phenols decreased from 38.1 to 13.4-17.2. Generally, almost of phenols reduced during the reaction, alkylated phenols like cresol, 2,4-dimethyl phenol, or 4-ethyl phenol were strikingly decreased. Therefore, it was suggested that phenol

In this experiment, a primary alcohol was converted into a primary bromoalkane using hydrobromic acid. The reaction was done under reflux and then distilled to obtain a product of higher purity. The degree of the alkyl halide obtained from the experiment was tested with silver nitrate and sodium iodide. An infrared (IR) spectra and the weight of the product were obtained for further analysis. The IR gave information on the present functional groups and product weight was used to calculate the percent yield.