LAB 7: ORGANOMETALLIC REACTIONS: IDENTIFICATION OF AN UNKNOWN BROMIDE (Preparative) Introduction The first purpose of the lab was to prepare an unknown organomagnesium bromide, an organometallic reagent, reacting an unknown aryl bromide with magnesium in anhydrous ether. The unknown was chosen from a predetermined list of benzoic acid derivatives with varying molecular weights and melting points (see Supplement C). The second purpose of this lab was to prepare an unknown carboxylic acid by reacting the unknown aryl-magnesium bromide with carbon dioxide and diethyl ether then protonating.The third purpose of this lab was to determine the neutralization equivalence point of the unknown carboxylic acid by titrating with sodium hydroxide. The fourth purpose of this lab was to ascertain the identity of the unknown carboxylic acid, and thus the original unknown aryl bromide, using its molecular weight determined from neutralization and melting point. Data and Results Compound Molecular Weight (g/mol) Melting Point (°C) Unknown Carboxylic Acid (R--COOH) 121.18 116-119 Discussion Organometallic reagents are compounds with carbon-metal (R--M) bond. In the carbon-metal bond, carbon is more electronegative than the metal atom which creates a dipole moment where carbon possesses a partial negative charge and the metal atom possessing a partial positive charge (Rδ---Mδ+). The partial negative charge on the carbon allows it to act as a strong nucleophile or base similar to
The original 1.0 gram of the 50/50 mixture of the benzoic acid and benzil contain 0.5 gram of benzil. Thus, from 0.5 gram of benzil, only 0.266 gram of benzil was collected. The percent recovery of benzil was calculated to be 53.2%. This low percent recovery could be due to filtration errors. Some amount of benzil remained on the filtration paper that contained the MgSO4. In order for determining the purity of the
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,
6. Summarize in a few sentences the halogenation and controlled oxidation reactions of 1°, 2°, and 3° alcohols.
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.
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
In the Cannizaro reaction an aldehyde is simultaneously reduced into its primary alcohol form and also oxidized into it 's carboxylic acid form. The purpose of this experiment is to isolate, purify and identify compounds 1 and 2 which contain 4-chlorobenzaldehyde, methanol, and aqueous potassium hydroxide. Compounds 1 and 2 are purified by crystallization. . The purified product will be characterized by IR spectroscopy and melting point.
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.
6. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene; to purify the crude product of either trans-stilbene, cis-stilbene, or styrene reaction.
The purpose of this experiment is to examine the reactivities of various alkyl halides under both SN2 and SN1 reaction conditions. The alkyl halides will be examined based on the substrate types and solvent the reaction takes place in.
The neutral was weighed and the mass of the compound and its flask together were recorded. The acid and base were each scraped onto weigh paper on a zeroed scale using a metal scoop. The mass of these products was also recorded. Identifying Compounds in Unknown B by Melting Point:
In this experiment, we were given three main goals to accomplish. We were to identify the compound through a series of organized experiments and analyze as many physical chemical properties as possible.
To stabilize the structure, the negative bromide was introduced via backside attack and made an anti product.
Grignard was the child of a sail producer. In the wake of concentrating on arithmetic at Lyon he exchanged to science and found the manufactured response bearing his name (the Grignard response) in 1900. He turned into an educator at the University of Nancy in 1910 and was granted the Nobel Prize in Chemistry in 1912. Amid World War I, he studied chemical warfare agents, especially the produce of phosgene and the identification of mustard gas. His partner on the German side was another Nobel Prize–winning chemist, Fritz Haber. (2) The Grignard reagent is exceptionally responsive and responds with most natural mixes. It likewise responds with water, carbon dioxide and oxygen. (2) Grignard reagents are set up by the response of magnesium metal with fitting alkyl halide in ether dissolvable. The halogen might be Cl, Br, or I. A standout amongst the most imperative employments of the Grignard Reagent is the response with aldehydes and ketones to frame liquor. A related blend utilizes ethylene oxide to plan alcohols containing two more carbon molecules than that of the alkyl halide. (2)
Organometallic are the most commonly compounds used in homogeneous catalysis. They usually contain various kinds of metals. Their reactivity, bonding (ionic and covalent or in-between) and stabilities are premised on 18 electrons rule. Organometallic compounds contain at least 1 carbon to metal bond. There are also organometallic complexes which have covalent bonds between organic ligands and a metal. The metal binds to ligands through an atom e.g. O2 or N; such compounds are referred to as coordination compounds. The complexes are basic in nature, also as reducing agents act as superoxide anion scavengers which help in catalyzing polymerization reactions and thus used clinically to treat tissues and cell injuries be it lymphomas or carcinomas. Rhodium compounds is analogues to the corresponding Platinum and Ruthenium compounds serve as effective anticancer agents due to significant antitumor properties. Effective advanced technologies such as nuclear magnetic resonance (NMR) and infrared spectroscopy (IR) are used to determine the dynamic properties, structures and industrial uses of organometallic compounds and complexes due to the ability to absorb the available proton occupied each site of a metal atom in the solution.
Coordination chemistry, which is the chemistry of metal complexes, is an important and fascinating branch of chemistry. The coordination compounds including organometallics are of significant importance and play a pivotal role in industry, technology and life processes. Due to their potential applications in various fields it has always fascinated and inspired chemists all over the world. This can be evidenced by the vast prolificity and scope of research papers on the subject in recent times and also by the diversity in which it has found applications.