Synthesis of Triphenylmethanol Using the Grignard Reaction and Acid Workup Amanda Sokol Partner: Jack Platacz TA: Edgar Reyes Cruz Lab: Tuesday, 1:40 - 4:30 PM PSH 334 March 17, 2023 Abstract: The purpose of this experiment was to synthesize pure triphenylmethanol by preparing and performing the Grignard reaction followed by an acid workup step. The two-week process combined various techniques used in lab this semester thus far with some new techniques; the first week involved making the Grignard reagent and its reaction with Benzophenone, while the second week consisted of hydrolysis as well as extraction and purification of the product through recrystallization. The solid product was also characterized through melting point and infrared spectroscopy. Ultimately, the melting point range of pure triphenylmethanol was 162.1°C - 163.9°C. The experiment yielded 29.45% crude …show more content…
When the Grignard was prepared, magnesium was the limiting reactant and bromobenzene was in excess. Benzophenone was the limiting reactant in the Grignard reaction, and thus, benzophenone is used as the limiting reagent in the calculations below. After the experiment, the weight of the crude product was measured to be 0.460 g, and the weight of the pure product was 0.350 g. The molar mass of triphenylmethanol was found to be 260.3 g in the pre-lab. Thus, using the theoretical yield (Equation 3) and the weights of crude and pure product discovered, the percent yield of crude product (Equation 4), the percent yield of pure product (Equation 5), as well as the percent recovery (Equation 6) were determined. Moles of the Reactants: Moles of bromobenzene = weight of bromobenzene (g)molecular weight (g/mol) = 1.218 g157.01 g/mol = 0.0078 mol Moles of magnesium = weight of magnesium (g)molecular weight (g/mol) = 0.153 g24.3 g/mol = 0.0063
Marissa De la Paz 29 October 2015 Landstrom T/R, 8am Experiment 13B: Phenyl Grignard Addition to Benzophenone The objective of this experiment is to first generate a Grignard reagent, then use that to synthesize triphenylmethanol. The Grignard reagent is necessary to create a new C—C bond. The formation of triphenylmethanol is broken down in several steps.
In order to find the amount of a product made during a double displacement reaction, the product has to be separated from the solution. From this number of moles of precipitate can be calculated. From there the number of moles of reactants can be calculated using the mole ratios of the particular reaction that occurred. As seen in Table 5 it is shown that by finding out the number of moles of the unknown, the molar mass of the unknown can be calculated. From the found mass of the unknown compound, the mound of the original ion can be found.
In this experiment, the combined reactions are as follows. To start the experiment, the Grignard reagent, phenylmagnesium bromide, was formed by reacting bromobenzene with magnesium while using anhydrous diethyl ether as the solvent. Using anhydrous ether is crucial because if any water is present, the Grignard reagent will react with the water instead, which will ultimately terminate the reaction. Once formed, the Grignard reagent reacted with the benzophenone to form triphenyl magnesium bromide; this served as the Grignard adduct. From there, the Grignard adduct underwent an acid workup using aqueous 6M hydrochloric acid in order to form the product triphenylmethanol.
The data observed and recorded in this lab shows that the concentration of miracle gro’ does affect the growth rate and germination speed of black eyed peas. The data is shown through two graphs and two data tables. The control group in this experiment is the seeds with a 0% concentration of miracle gro’, therefore the seeds with just water. The experimental groups are different concentrations of miracle gro’ including a 10%, 15%, 20%, 25%, and 30% concentration. The variable in this experiment is the amount/concentration of miracle gro’.
This resulted in a 7.2% yield of pure TPM and a percent recovery of 16%. Evidently, TPM was lost throughout the experiment and/or it was not completely synthesized. The first crude yield of 69% suggests that loss of product may have occurred during the synthesis of TPM and/or the washing/extraction process. Some of the magnesium may not have reacted with the bromobenzene to yield the Grignard reagent.
A mixture of 0.25 g of camphor (1.64 mmol), 1.5 mL of methanol, and 0.25 g of sodium borohydride (6.60 mmol, NaBH4) was boiled for 2 minutes. Moreover, the addition of 10 mL of ice deionized water resulted in a white solid after the organic solution was vacuum filtered. The organic solid was dissolved in 10 mL of dichloromethane (CH2Cl2) and small amounts of anhydrous sodium sulfate (NaSO4) to dry. The organic solution was decanted and evaporated for melting point (203.3-203.8 °C), NMR, and IR spectroscopy. Product formation and heats of formation (borneol = -1.203675E6 kJ/mol, isoborneol = -1.203687E6 kJ/mol) were analyzed.
Mass of BaCl₂∙2H₂O for trial 1 (m_(BaCl^2∙2H^2 O))=( mol BaCl_2∙2H_2 O)|(244.3 g BaCl_2∙2H_2 O )/(1 mol BaCl_2∙2H_2 O) (m_(BaCl₂∙2H₂O))= 5.187×〖10〗^(-4) mol BaCl_2∙2H_2 O|(244.3 g BaCl_2∙2H_2 O )/(1 mol BaCl_2∙2H_2 O) (m_(BaCl₂∙2H₂O))=0.1267g BaCl₂∙2H₂O The percent composition of the limiting reactant (% comp) was calculated by dividing the mass of the limiting reactant (m_(BaCl₂∙2H₂O)) by the mass of the original sample (m_s) and multiplying the product by 100 Percent composition of BaCl₂∙2H₂O for trial 1 (% comp)= ((m_(BaCl₂∙2H₂O)) )/((m_s) ) ×100 (% comp)= ((0.1267g BaCl₂∙2H₂O ) ) /((1.0490g) )
From the infrared spectra, it showed that the reaction went to completion and benzaldehyde oxime was produced. Key aspects which indicate the reaction wen to completion are; Stretch of C=N (aldoxime) 1633 cm-1 indicating that oxidation of the aldehyde had occurred, and also 953 cm-1
Based on the products made, my predictions of chemical reaction type were correct. The reaction between lead (II) nitrate and potassium iodide can also be categorized as a redox reaction. The reaction between magnesium metal and hydrochloric acid can also be categorized as a neutralization reaction. The investigation can be explored further by varying the concentration of reactants, the temperature, and the mass of the reactants. Additionally, the effect of catalysts on the reaction rate could be
The cylinder with the sebacoyl chloride was 27.14 grams and the cylinder with hexamethylenediamine was 36.14 grams. We then calculated the mass of the reactants, which is found when we found the difference of the weight of the cylinders before and after sebacoyl chloride and hexamethylenediamine were added. The total mass of the reactants was equal to 41.35 grams. After we calculated these results, we started to create the chemical reaction. We put the sebacoyl chloride and the hexamethylenediamine in separate beakers, but then slowly added the hexamethylenediamine to the beaker with the sebacoyl chloride in it.
Introduction: The objective of the experiment is to determine the limiting reagent in a chemical reaction. The principles of stoichiometry and limiting reagents will be used to predict the amount of product formed. The amount of product formed and the change in the color of the solution upon mixing of two reactants are being used to predict the limiting reagent and calculate the theoretical yield in grams. My hypothesis was that with the reaction of the zinc with the copper sulfate solution that it would dissolve the zinc to determine the limiting reagent.
The purpose of this lab is to use the Diels-Alder reaction to combine anthracene and maleic anhydride. Named after its two founders the Diels-Alder reaction is the addition of a conjugated diene (electron rich compound) with a dienophile (electron poor compound). (1) These compounds will be combined using [4+2] cycloaddition, where the numbers 4 and 2 come from the number of π electrons that are used in each compound to synthesize the product. (2) This experiment comes at the cost of losing two π bonds to form two new sigma (σ) bonds in the cyclic compound. (2)
The crude oil is heated in a tall cylinder called fractionator for at least 350 degC. The process is based on the principle that different substances boil at different temperature. The cyclohexane content of naphtha fraction of crude oil can vary from 0.5 to 5.0 volume %. N-hexane, isohexanes, methyl cyclopentane, benzene and dimethyl pentanes have normal boiling points very close to cyclohexane.1 Advantages: 1. Uses a simple method of cyclohexane recovery. Disadvantages: 1.
The percent yield was 22.33%. In most cases, that means that a lot of possible product was lost. However, in this case, that was not true. When Benzaldehyde reacted with the Wittig reagent, it produced two products: E-Stilbene and Z-Stilbene. The Z product was a liquid, while the E product was a solid.
.048 1.0 94.1 Experiment Two Methanol (MeOH) And Water (H2O) .049 .045 Methanol – 1.5 Water – 0.5 92 Conclusion Both experiments were of fair solubility, but in the case of recrystallization of Benzoic Acid, Water was the best solvent to recrystallize acid the most. Experimental data determined that there was a difference of .003g between using the single solvent in comparison to the paired solvent.