Synthesizing Triphenylmethanol Using A Grignard Reagent

Any amount of H2O present would react with and therefore ruin the Grignard reagent. The negative charge on the Grignard carbon would pop a proton off of water, and the resulting hydroxide would react with MgBr2. Since all of the water and moisture was removed, the reaction should run successfully. For this experiment’s reaction, bromobenzene is turned into phenylmagnesium bromide, a Grignard reagent. Then, the Grignard reagent is reacted with benzophenone to yield a molecule with a negative charge on the oxygen. This molecule is worked up and protonated to yield triphenylmethanol.

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,

During the halogenation reactions of 1-butanol, 2-butanol, and 2-methyl-2-propanol, there is a formation of water from the OH atom of the alcohol, and the H atom from the HCl solution. The OH bond of the alcohol is then substituted with the Cl atom. Therefore all of the degrees of alcohol undergo halogenation reactions, and form alkyl halides as products. This is because the functional group of alkyl halides is a carbon-halogen bond. A common halogen is chlorine, as used in this experiment.

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.

The Purpose of this experiment is for the students to learn how to use sodium borohydride to reduce benzil to its secondary alcohol product via reduction reaction. This two-step reaction reduces aldehydes by hydrides to primary alcohols, and ketones to secondary alcohols. In order for the reaction to occur and to better control the stereochemistry and yield of the product, the metal hydride nucleophile of the reducing agents such as LiH, LiAlH4, or NaBH4 must be carefully chosen. Being that LiAlH4 and NaBH4 will not react with isolated carbon-carbon double bonds nor the double bonds from aromatic rings; the chosen compound can be reduce selectively when the nucleophile only react with

The synthesis of acetaminophen involves the attraction of the electrophilic carbonyl group of acetic anhydride to the nucleophilic NH2

For this experiment, an organometallic reagent was used for the synthesis and isolation of benzoic acid. The Grignard reaction is the addition reaction of an organometallic reagent, which in this case was an organomagnesium reagent. An organometallic reagent is a carbon bonded to a metal. This reagent was combined with an electrophile, a carbonyl compound such as a ketone or aldehyde. Carbons are electrophilic when bound to a nonmetal thus the atoms are more electronegative than the carbon and metals are less electronegative than carbon.

In this experiment, the goal is to prepare a Grignard reagent from an unknown aryl halide and identify the identity of the aryl halide by converting it to a carboxylic acid to determine its melting point and molar mass (determined by titration). The experiment began by dissolving 0.25g of magnesium powder in a 25mL round-bottom with 5mL of anhydrous ether and stirring with a stir bar. Then the round-bottom flask was set up for reflux using a Claisen adapter where the vertical part is covered with a septum to prevent air from mixed with the solution. The septum is very important because the Grignard product can react with oxygen to produces a carboxylic acid, which is not wanted. Also, the choice of anhydrous solvent is important because the Grignard product can react with water to produce an alkane. With the reflux set up, the next step was to add the halide. 1.2mL of the unknown bromoarene mixed with 2.5mL ether was slowly added dropwise through the septum using the needle and syringe. The bromoarene had to be added slowly because there Grignard product would undergo another unwanted side reaction by reacting with the unknown bromoarene. The product with be a new carbon-carbon bond between the unknown bromoarene and the Grignard product. If the bromoarene is added slowly, the chances of the Grignard product reacting with the bromoarene over the magnesium is low because magnesium exists in larger concentration in the solution. Once all the unknown bromoarene

Distillation. Transfer the clear liquid to a dry 25-mL round-bottom flask using a Pasteur pipet. Add a boiling stone and distill the crude t-pentyl chloride in a dry apparatus. Collect the pure t-pentyl chloride in a receiver cooled in ice. Collect the material that boils between 78°C and 84°C. Weigh the product and calculate the percentage yield.

The Grignard reaction is an important synthetic process by which a new carbon to carbon bond is formed. Magnesium metal is first reacted with an organic halide forming the Grignard reagent. The Grignard reaction is the addition of an organomagnesium halide (Grignard reagent) to a ketone or aldehyde, to form a tertiary or secondary alcohol, respectively. For example, the reaction with formaldehyde leads to a primary alcohol. Grignard Reagents are also used in the following important reactions: The addition of an excess of a Grignard reagent to an ester or lactone gives a tertiary alcohol in which two alkyl groups are the same, and the addition of a

In a 25-mL round-bottom flask, 1-chlorobutane (5 mL, 4.32 g, 0.046 mol), sulfuryl chloride (1.6 mL, 2.7 g, 0.02 mol), 2,2’-azobis-(2-methylpropionitrile) (0.03 g), and a boiling chip were added. After a condenser and gas trap were attached to the flask, the mixture was heated to a gentle reflux in a steam bath for 20 min. The flask was then allowed to cool down quickly in an ice bath for a short time before a second portion of the 2,2’-azobis-(2-methylpropionitrile) (0.03 g) was added to the flask. The mixture was refluxed for another 10 min. before the flask was cooled in a beaker of water. The reaction mixture was then poured into a small separatory funnel already filled with water (10 mL),

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

Through the use of the Grignard reaction, a carbon-carbon bond was formed, thereby resulting in the formation of triphenylmethanol from phenyl magnesium bromide and benzophenone. A recrystallization was performed to purify the Grignard product by dissolving the product in methanol. From here, a melting point range of 147.0 °C to 150.8 °C was obtained. The purified product yielded an IR spectrum with major peaks of 3471.82 cm-1, 3060.90 cm-1, 1597.38 cm-1, and 1489.64 cm-1, which helped to testify whether the identity of the product matched the expected triphenylmethanol. The identity of the product being correct was further confirmed by way of both proton and carbon-13 NMR spectra. This is due to the fact

The purpose of this lab was to synthesize triphenylmethanol from benzophenone and bromobenzene by the formation of a Grignard compound with the reagents bromobenzene and magnesium metal. The bromobenzene was first transformed into the Grignard compound and was then reacted with the benzophenone to make the final product. The mixture was then mixed with sulfuric acid and the organic layer was extracted via a separatory funnel. The mixture was then recrystallized from methanol and was allowed to dry and the percent yield, melting point, and the IR was obtained. The mass of the product obtained was 5.45 grams and the percentage yield was determined to be 41.95%. The melting point range obtained from the final product was 89-91°C

Cinnamaldehyde, cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil, extracted from several species of Cinnamomum (C. verum, C. burmanii, C. cassia), under the family Lauraceae, a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil, which contains 60-80% cinnamaldehyde, 4-5% sesquiterpenoids (α-humulene, β-caryophyllene, limonene and others), eugenol, cinnamyl acetate, eugenol acetate, cinnamyl alcohol, methyl eugenol, benzaldehyde, benzyl benzoate, cuminaldehyde, monoterpenes (linalool, pinene,