Grignard Limiting Reagent

Decent Essays
The main purpose of this experiment is to perform the Grignard reaction and synthesize, extract, purify and characterize the product of triphenylmethanol. The Grignard reagent was first synthesized using a nucleophilic addition reaction. The Grignard adduct was then hydrolyzed to form triphenylmethanol. The organic layer was extracted using diethyl ether, petroleum ether, brine and a separatory funnel. The theoretical percent yield was first calculated by finding the limiting reagent for this reaction. The limiting reagent was found to be benzophenone and the theoretical yield was found to be 0.00598 mols of triphenylmethanol. The percent yield of the crude and pure product of triphenylmethanol was calculated to be 32.05% and 27.4% respectively.

Related Documents

  • Improved Essays

    Ethyl vinyl ether was used to protect –OH on glycidol based on a literature reported protocal.59 In a typical procedure, 0.675 mol glycidol and 200 mL ethyl vinyl ether were loaded in a round-bottom flask, to which 1.25 g TsOH was then added. The reaction was allowed to proceed at room temperature (RT) for 3h. The resulting mixture was then purified by washing with 100 ml saturated aqueous solution of NaHCO3 for 3 times. The organic layer obtained was dried by MgSO4. After filtration of MgSO4, the excess ethyl vinyl ether was removed by rotary evaporation.…

    • 988 Words
    • 4 Pages
    Improved Essays
  • Decent Essays

    Spacer Lab Report

    • 393 Words
    • 2 Pages

    General procedure: One equivalent of spacer was coupled using 2.4 equivalents of inhibitor, 0.18 equivalents of copper sulfate, 0.36 equivalents of (+)-sodium-L-ascorbate, in a mixture of 10% H2O in DMF, 24 mL/mmol spacer. The mixture was placed in the microwave for 30 minutes at 80oC Pro6 Spacer (10) (30 mg, 0.036 mmol) and 18 (36 mg, 0.087 mmol) were dissolved in 778 µL DMF. Copper sulfate (1.62 mg, 0.006 mmol) and sodium-L- ascorbate (2.57 mg, 0.013 mmol) were dissolved in 86 µL H2O. The two solutions were combined in a microwave tube and put in the microwave for 30 minutes at 80oC. The solvent was evaporated under reduced pressure.…

    • 393 Words
    • 2 Pages
    Decent Essays
  • Great Essays

    The neutralization of the reaction was verified using pH paper to test whether the pH was neutral or slightly basic. At this point, the two possible products in the round bottom flask could have been exo- and endo-norborneol. Extraction and washing was performed and the exo- and endo-norborneol products formed were extracted into dichloromethane due to their similar solubilities, where the two products are overwhelmingly non-polar despite the one hydroxyl group. The dichloromethane (DCM) was the bottom layer formed, while the aqueous layer, the layer that was washed away, was the top and this was due to the weight of the chlorine atom that made DCM more dense. Extraction was repeated several times due to the partition coefficient, as it theorizes how smaller extractions are better than bigger extractions because they yield more concentrated extractions in the end.…

    • 1629 Words
    • 7 Pages
    Great Essays
  • Improved Essays

    Dichromate To Isoborneol

    • 892 Words
    • 4 Pages

    The percent yield of isoborneol (part two) was determined to be 36.7% with the limiting reagent being camphor. If this reaction was repeated, more care would have been taken when subliming the product by controlling the temperature to make sure only camphor and isoborneol got sublimed. However, based on the IR spectra’s obtained camphor and isoborneol, the reaction did successfully oxidize borneol to camphor showing the formation of the key carbonyl group, and the reaction to reduce camphor to isoborneol did somewhat go to completion with the key hydroxyl group but it did show a carbonyl group present, which is not present in the true isoborneol IR spectrum. The 1H NMR also showed good experimental evidence of isoborneol being preferred (major product) over…

    • 892 Words
    • 4 Pages
    Improved Essays
  • Decent Essays

    solution, because it is the source of the Grignard reagent. Because the halide cannot be eliminated, the next best option is to minimize the amount of halide in the reaction. In this experiment, a small concentration of the halide is reacted with a high concentration of magnesium to ensure maximum contact between halides and magnesium. To do this, magnesium will be placed in the round bottom flask and then halides are slowly added. Another potential source of error is that Grignard reagents must be placed far away from water sources.…

    • 318 Words
    • 2 Pages
    Decent Essays
  • Superior Essays

    Then, p-nitrobenzeneazide (0.16 g, 1.0 mmol) was added. The mixture was stirred at room temperature until complete consumption of the starting materials, monitored by TLC. The reaction mixture was diluted with 25 mL of water, cooled in ice, and extracted with CH2Cl2 (3x15 mL). The combined organic extracts were washed with brine, and dried (MgSO4). After removal of the solvent under reduced pressure, the residue was purified on silica gel with n-hexane–ethylacetate (8:2) yielding the target compound 8 as colorless powder (0.42 g, 79%); mp: 182-183…

    • 1222 Words
    • 5 Pages
    Superior Essays
  • Great Essays

    Diels Alder Reaction Lab

    • 1317 Words
    • 6 Pages

    Introduction: As it is taught throughout school, all living things are made up of cells. These cells are carry out all the necessary functions to keep the human body well maintained including chemical reactions and other complex tasks. In order to carry out these functions, it’s vital for the cell to possess a membrane. Cells create cholesterol, which is a cyclic fatty-product that maintains the cells permeability. Cholesterol is also synthesized to create steroid hormones, and also vitamin D.…

    • 1317 Words
    • 6 Pages
    Great Essays
  • Improved Essays

    Before the start of this experiment, the theoretical yield was calculated. From the results, the limiting reagent is 3-nitrobenzaldehyde. The theoretical yield is determined by referring to the moles of the limiting reagent, which was calculated to be 1.3 g. However, the results obtained (Data Table 1) were greater than the theoretical yield; that is, the actual mass of the product was higher than the theoretical mass. This lead to an abnormally high yield of 320% and an impure product.…

    • 649 Words
    • 3 Pages
    Improved Essays
  • Improved Essays

    To demonstrate their effectiveness in creating new carbon to carbon bonds, the Grignard arylation of 2-butanone was carried out. The Grignard reaction of phenyl bromide and magnesium, followed by the addition of 2- butanone yielded a crude product of 2-phenyl-2-butanol. The 1H NMR spectra was taken before distillation, showing the crude product, as well as after distillation, showing one of greater purity. In addition, an IR spectrum was taken after distillation. Both the 1H NMR and IR spectra support the conclusion that the product is 2-phenyl-2-butanol.…

    • 294 Words
    • 2 Pages
    Improved Essays
  • Improved Essays

    Melting Point Value

    • 294 Words
    • 2 Pages

    A important tests were performed on the product to pressure the results: melting point value, percent yield, IR, and TLC. The experimental melting point value was found to be a range of 165-167 ºC being a little lower than the literature value for camphor, the intended product, was 175 ºC. The sharp range was resulted in a slightly pure product. The percent yield was lower than expected which can be the reason most of the product was lost during the extraction and almost completely sublimated during the solvent evaporation, which lead to vacuum filtration. As a known possibility, some ketone and alcohol was formed and could be associated with the borneol drying out an contaminating the water.…

    • 294 Words
    • 2 Pages
    Improved Essays
  • Great Essays

    Ethyl Cinnamate Synthesis

    • 921 Words
    • 4 Pages

    Experiment 5 Synthesis and NMR Spectroscopy of ethyl cinnamate Introduction: Wittig reactions involve the stereoselective synthesis of olefins from phosphonium ylides and aldehydes or ketones, where the carbonyl bond is converted to an alkene double bond.1 The variety of suitable reagents and the relatively mild experimental conditions facilitate their industrial applications, such as the synthesis of epoxides, esters, carotenoids and vitamin A.2,3 Specifically, the ester ethyl cinnamate is used as a flavouring agent and in perfumes. The diastereomers of the alkene are distinguished through Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy, where the coupling constants of alkenyl protons are different for (E) and (Z) isomers.4…

    • 921 Words
    • 4 Pages
    Great Essays
  • Decent Essays

    In a chemical equation, there are the reactants, which is the part that is changed, and the products, which is what is left over. The reactant side and the product side must have the same quantity of each element. If they do not, the equation must be balanced by using coefficients. Mole ratios can be found by using these coefficients. Mole ratios are conversion factors and can be used to found the amounts of the reactants and the products in a chemical reaction.…

    • 289 Words
    • 2 Pages
    Decent Essays
  • Improved Essays

    DISTILLATION The purpose of experiment 1, fractional distillation and gas chromatography, was to separate an unknown organic mixture into two liquids. The primary process of separation was fractional distillation, which utilizes the physical properties of the two unknown volatile liquids. Once the unknown mixture was successfully fractioned, gas chromatography was used to help determine the identity of the two unknown liquids. Fractional distillation and simple distillation both take advantage of two major physical properties to separate liquids.…

    • 1163 Words
    • 5 Pages
    Improved Essays
  • Improved Essays

    Introductions: The purpose of this experiment is to synthesize acetaminophen and esters in order to apply the process of retrosynthetic analysis to determine the unknown alcohols used to produce the esters. Acetaminophen, a popular active ingredient in many over-the-counter drugs, is used as a pain reliever and a fever reducer. It is synthesized from the reaction between a carboxylic acid and an amine; thus, acetaminophen contains hydroxyl and amide functional groups.1 C6H7NO + C4H6O3 C8H9NO2 + C2H4O2 This reaction is commonly known as a condensation reaction.…

    • 839 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Benzocaine was synthesized from p-toluidine in a four step synthesis. Each intermediate product, including N-acetyl-p-toluidine, p-acetamidobenzoic acid, and p-aminobenzoic acid, was checked for yield, presence, and purity through weighing, taking IR and NMR spectrums, and determining the melting point. Thin Layer Chromatography was used to ensure the completion of the final reaction from p-aminobenzoic acid to benzocaine. The yield of the first step from p-toluidine to N-acetyl-p-toluidine was 91.9%. The yield of the second step from N-acetyl-p-toluidine to p-acetamidobenzoic acid was 49.85% The yield of the third step from p-acetamidobenzoic acid to p-aminobenzoic acid was 32.49%, which was not enough to continue so some product was borrowed…

    • 878 Words
    • 4 Pages
    Improved Essays