Synthesis Of Triphenylmethanol Synthesis Lab Report

Running the reaction. The mixture in the 5-ml conical vial containing the tetraphenylcyclopentadienone and anthranilic acid was heated on an aluminum block to 140° C. Once the mixture started to boil the prepared mixture of isopentyl nitrite was added to the 5-ml conical vial through the top of the condenser using a pasture pipette. The solution continued to boil for 25 more minutes until a

A Sn2 reaction was conducted; this involved benzyl bromide, sodium hydroxide, an unknown compound and ethanol through reflux technique, mel-temp recordings, recrystallization, and analysis of TLC plates.

The triphenymethanol product was a very fine white powder that had a slight yellow tint to it. The experimental melting point was calculated to be 159.0-159.6°C, which is very accurate compared to the actual melting range of 160-163°C. The percent yield came out to be 26.89%, which is most likely low due to using heating plates to heat the end reaction instead of the recommended steam baths.

After adding the acetic acid and hydrobromic acid to the solution, and heating and recrystallizing the solution, the product triphenylmethyl bromide was created and had a mass of 0.103 g. The theoretical yield was calculated by determining the limiting reagent in the reaction. The triphenylmethanol was the limiting reagent in the reaction. The total amount of mass from the triphenylmethanol was converted to moles by using the molar mass of the triphenylmethanol. The amount of moles was then converted into grams to determine the theoretical yield, 0.125 g. The percent yield was then calculated by dividing the actual yield by the theoretical yield and multiplying the result by 100%. The percent yield was 82.4%. The melting point of the product was observed to be 139.5 °C. The theoretical yield of the product is 152 °C (University of South Carolina Department of Chemistry and Biochemistry). The melting point percent difference was calculated by subtracting the theoretical melting point from the actual melting point, dividing the result by the theoretical melting point, and multiplying the result by 100%. The melting point difference was 8.22%. Example calculations are shown

Four types of reactions will be performed in this experiment: precipitation reactions, redox reactions, decomposition reactions, and acid base

In the first step, the leaving group departs, forming a carbocation C+. In the second step, the nucleophilic reagent (Nuc :) attaches to the carbocation and forms a covalent sigma bond. If the substrate has a chiral carbon, this mechanism can result in either inversion of the stereochemistry or retention of configuration. Usually both occur without preference. The result is racemization. For an example (the reaction of tert-butyl chloride with water.)

On the other hand, the crude product versus the known product is similar which makes them identical. This also interprets to the products and reactants were pure. Then, the 2nd TLC plate was based on the interval of the student’s product while it was heating.. The TLC plate shows purity as well as the concentration gradually increasing. This is what prevents the spots from becoming darker during the 15 minute reflux process. The initial amount was 2.003 grams and the end product weighed 1.468 grams. The results show that the crude sample that was made from the lab had around the same purity with that of the known sample, thus, the experiment was

In the round-bottom flask (100 mL), we placed p-aminobenzoic acid (1.2 g) and ethanol (12 mL). We swirled the mixture until the solid dissolved completely. We used Pasteur pipet to add concentrated sulfuric acid (1.0 mL) to the flask. We added boiling stone and assembled the reflux. Then, we did reflux for 75 minutes. After reflux, we removed the reaction mixture from the apparatus and cooled it for several minutes. We transferred the mixture to the beaker that contained water (30 mL). We cooled the mixture to room temperature and added sodium carbonate to neutralize the mixture. We added sodium carbonate until the pH of the mixture was 8. After neutralize, we collected benzocaine by vacuum filtration. We used a Buchner funnel to collect benzocaine. We used three 10 ml of water to wash the product. After the product was dry, we weighed, calculate the percent yield and determined the melting point of the product.

Based on the observation that the tubes containing PTA and citric acid were the only tubes that showed no color change, it was assumed that the ion of copper that the two the chelating agents bonded was necessary for the reaction. Otherwise, if it was not necessary, color change, from clear to brown, would have occurred signaling that the enzyme, catecholase, did catalyze the conversion of catechol to benzoquinone.

In order to overcome this issue, the reaction could have been performed in a regular solvent heated to 190C under extremely high pressure to prevent boiling. However, the lab was not equipped to safely deal with high pressure situations, so instead a solvent with an extremely high boiling point had to be used. In this case, triethylene glycol, which has a boiling point of 260℃, was used. This boiling point is significantly higher than the 190℃ that this reaction was performed at, and the solvent would hence not boil away, even under standard pressure

The goal of this experiment was to covert 1-butanol into 1-bromobutane. By reacting 1-butanol with bromine, a nucleophilic substitution would occur where the alcohol group from 1-butanol is replaced with a bromine. In order for the -OH group to depart, its conjugate acid would have to be a strong acid. The conjugate acid for a hydroxyl group is water, which is a weak acid. To get the reaction to occur, 1-butanol would have to be reacted with sulfuric acid to protonate the -OH group. The leaving would then be a water, with a conjugate acid of hydronium (H3O+), which is a very strong acid. The reaction would then follow either the SN1 or SN¬2 mechanism. The SN1 mechanism is characterized by two steps. The first is heterolytic cleavage, where the leaving

One conformation placed the 4-tert-butyl substituent in most stable, locked the equatorial position with the carbonyl pointing up. Oxidation the 4-tert-cyclohexanol produced a greater amount of the more stable conformer with tert-butyl in the equatorial position relative to the conformer with tert-butyl in the un-favored axial position. The faces of 4-tert-butylcyclohexanone are non-equivalent for nucleophilic attack due to top –face steric hindrance imposed by a tert-butyl group in the equatorial position and the presence of much smaller, axial deuterium atoms adjacent to the carbonyl on the bottom-face of the

The apparatus for the addition reaction under reflux was assembled. Magnesium (1 g) was weighted on a paper, and a few pieces of magnesium were crushed in order to activate the metal surface. Then, the round bottom flask was lowered away from the condenser, and the magnesium was added to it. After that, 10 ml of anhydrous diethyl ether was added in a round bottom flask by using the syringe, and the reaction flask was heated using a heating mantle to maximize the formation of the Grignard reagent. After 10 minutes of heating the mixture, the mixture changed color from clear to yellowish, and it turned completely Reddish brown after 12 minutes. After 28 minutes, the mixture stopped boiling, and approximately 4.5 ml of bromobenzene was added drop by drop in the mixture, and color of the mixture was turned light brown orange. Then, the phenylmagnesium bromide was cooled in ice bath for a few minutes, and 10 ml of anhydrous diethyl ether was added in the mixture by using the syringe. After that, approximately 2.3 ml of methyl benzoate was added to the reaction, and it was added slowly slowly because the reaction was exothermic which needed to be cool in order to maintain a gentle reflux. Once all the methyl benzoate solution was added, the heating mantle was removed from the reaction flask and was cooled to the room temperature. During the reaction, a milky white salt began to precipitate, and the reaction flask was swirled for ten minutes until most of the reaction became visibly subdivided. The contents of the reaction flask were slowly poured into the 250 ml Erlenmeyer flask which already contained 13.75 g ice and 25 ml of 10% H2SO2. The round bottom-flask was rinsed with 2.0 mL of 10% H2SO4 and 2.0 mL of diethyl ether, and the rinses were added to the mixture in an Erlenmeyer flask. Then, the mixture was swirled until all the salt was hydrolyzed, and the product distributed well into the ether layer. A

A plausible mechanism for the synthesis of an isoquinolin-1-yl-arylmethanone is depicted in Scheme 5. The synthetic cycle is assumed to begin with the reaction of Aliquat 336 as the phase transfer catalysis and K2S2O8 as a dehydrogenative reagent to generate the salt A, which then would convert to the sulfate radical B by heating. Sulfate radical B could react with the benzyl alcohol 1a through a hydrogen abstraction process providing an acyl radical C. Further addition of acyl radical C to the isoquinoline 1a

Buffer having pH 3.70 used as Mobile phase A and mixture of methanol, acetonitrile and tetrahydrofuran (50: 50: 2 v/v/v) were used as Mobile phase B.