Kolbe-Schmitt Reaction Kira Wall (CHE433) 12-3-14 The Kolbe-Schmitt reaction is named after Hermann Kolbe and Rudolf Schmitt. Schmitt published his research in the Journal fur Pracktische Chemie in 1885 while Kolbe published his research in the Annalen der Chemie und Pharmacie in 1860. The reaction adds a carboxyl group onto the benzene ring of a phenol. The process uses a base carbon dioxide and acid work-up. The original reaction done by Kolbe involved the formation of sodium phenoxide through the evaporation of a molar equivalent mixture of phenol and aqueous sodium hydroxide. The hygroscopic sodium phenoxide is then heated while carbon dioxide gas is passed over the molten salt. The mixture is then further heated to give the dianion of salicylic acid along with carbon dioxide and phenol both of which distill away from the mixture. Under these …show more content…
They found that carbon dioxide needed to be activated to build hydroxybenzoic acids with alkali metal phenoxide. They came to this realization by coordinating the alkali metal with the carbon dioxide. This caused the formation of the MOPh-CO2 complex. As the carboxylation reaction proceeded, a direct carboxylation of the benzene ring with another molecule of carbon dioxide did not take place, instead, the CO2 moiety of the MOPh-CO2 complex performed an electrophilic attack on the benzene ring in the ortho and para positions. It was shown that the intramolecular conversion of the MOPh-CO2 complex was the most responsible for the products distribution of the Kolbe-Schmitt reaction. It was observed that the mechanism of the carboxylation reaction of lithium phenoxide was significantly different from those of other alkali metal phenoxides however, there was a resemblance between the mechanisms of the carboxylation reactions of lithium phenoxides and sodium
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
Cadet Eric Wiggins Date: 18 September 2014 Course Name: Chem 100 Instructor: Captain Zuniga Section: M3A Identification of a Copper Mineral Intro Minerals are elements or compounds that are created in the Earth by geological processes. The method of isolating metals in a compound mineral is normally conducted through two processes.
1. Identify the range of senses involved in communication • Sight (visual communication), Touch (tactile communication), Taste, Hearing (auditory communication), Smell (olfactory communication) 2. Identify the limited range of wavelengths and named parts of the electromagnetic spectrum detected by humans and compare this range with those of THREE other named vertebrates and TWO named invertebrates. Figure 1: the electromagnetic spectrum source: www.ces.fau.edu Vertebrates Human Japanese Dace Fish Rattlesnake Zebra Finch Part of electromagnetic spectrum detected ROYGBV (visible light) detected by light sensitive cells in the eye called rods and cones.
Grignard is a reaction that is crucial to forming the new carbon-carbon bond. This is a two-part lab that teaches new techniques; the purpose of this lab is to introduce realistic organic synthesis and apply acid workup to produce triphenylmethanol. A Grignard reaction is characterized by the addition of a magnesium halide (an organomagnesium halide) to an aldehyde or a ketone in order to form a secondary or tertiary alcohol. These reactions are helpful because they serve as a crucial tool in performing important carbon-carbon bond-forming reactions (Arizona State University, 2018). This experiment aimed to observe the mechanisms of a Grignard reply to synthesize triphenylmethanol from benzophenone using phenylmagnesium bromide as the Grignard reagent.
The most common atom to be replaced is a hydrogen atom, but occasionally other atoms may also be swapped out by an electrophile. Within this reaction, the substituents connected to the benzene ring demonstrate directing behavior that can affect the formation of the product. These substituents can either act as an ortho/para or meta director, which ultimately determine where the electrophile is added onto the ring. Figure 2. Bromine Production via Potassium Bromate and Hydrobromic Acid.1
The goal of the experiment is to synthesize a bromohexane compound from 1-hexene and HBr(aq) under reflux conditions and use the silver nitrate and sodium iodide tests to determine if the product is a primary or secondary hydrocarbon. The heterogeneous reaction mixture contains 1-hexene, 48% HBr(aq), and tetrabutylammonium bromide and was heated to under reflux conditions. Heating under reflux means that the reaction mixture is heated at its boiling point so that the reaction can proceed at a faster rate. The attached reflux condenser allows volatile substances to return to the reaction flask so that no material is lost. Since alkenes are immiscible with concentrated HBr, tetrabutylammonium bromide is used as a phase-transfer catalyst.
The purpose of this experiment was to learn about the electrophilic aromatic substitution reactions that take place on benzene, and how the presence of substituents in the ring affect the orientation of the incoming electrophile. Using acetanilide, as the starting material, glacial acetic acid, sulfuric acid, and nitric acid were mixed and stirred to produce p-nitroacetanilide. In a 125 mL Erlenmeyer flask, 3.305 g of acetanilide were allowed to mix with 5.0 mL of glacial acetic acid. This mixture was warmed in a hot plate with constantly stirring at a lukewarm temperature so as to avoid excess heating. If this happens, the mixture boils and it would be necessary to start the experiment all over again.
The reaction to synthesize benzocaine was known as a Fisher esterification reaction. The Fisher esterification was reaction between alcohol and carboxylic acid in the presence of acid. The reaction was used to form an ester. In the experiment, sulfuric acid acted as a catalyst and necessary for this reaction to occur. There was a change between the –OH group of carboxylic acid to an –OCH2CH3 group in the reaction.
Chem 51 LB Experiment 3 Report Scaffold: Bromination of Trans-Cinnamic Acid 1. The goal of this experiment was to perform a halogenation reaction through the addition of two bromides from pyridinium tribromide. This was accomplished by reacting trans-cinnamic acid with pyridinium tribromide. After the reaction took place, melting point analysis was conducted to find out the stereochemistry of the product, which could either be syn-addition, anti-addition, or syn + anti-addition. 2.
Lab IV – Stoichiometry Lab Investigation Liam Farhangi Chemistry, Period 4 Dr. Juan Bacigalupi January 13, 2023 Lab IV – Stoichiometry Lab Investigation - Abstract Short (100-150 word) summary of the investigation (research question, conclusion, one-sentence summary of procedure, problems, or suggestions for additional research). Goes first, done last. Lab IV – Stoichiometry Lab Investigation The introduction includes (do not forget to indent each paragraph): Paragraph 1 includes the research question, the hypothesis, and the purpose of the investigation Question Part 1 How many moles of carbon dioxide are produced in the reaction of sodium bicarbonate and acetic acid in the video lab?
Experiment 2 Report Scaffold (Substitution Reactions, Purification, and Identification) Purpose/Introduction 1. 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. 2. There was one unknown compound in the reaction that was later discovered after a series of techniques described above.
It is understood the mechanism is acid-catalyzed where protons coordinate with the carbonyl oxygen to make the carbonyl carbon more electropositive for nucleophilic attack (Scheme 1). In the experimental procedure all reactants were added together, this is inefficient as the protons can coordinate with either trans-cinnamic acid or methanol. Coordination with methanol is unnecessary as it reduces its nucleophilicity and makes less protons available to coordinate with the carboxylic acid. To improve
This was proved by utilizing the IR spectrum to verify the C =O was not in the final product as it lacked the 1640 cm-1 peak. The melting point of 113-115 degrees C proved that the final product obtained was the E-Stilbene. The TLC plate proved that the E and the Z product was produced, show cased by the double intensity of the DCM spot to the final product’s spot, both which had an Rf of 0.92. The double intensity proved that both products were produced, but through heating and filtering, the Z-Stilbene was
In Experiment One we will be recrystallizing Benzoic Acid from water. In Experiment Two we will be recrystallizing Benzoic Acid using a solvent pair made up of Methanol and Water. The Seven step process of recrystallization consists of adding a solid organic substance into a solvent, then dissolving the chosen solute, decolorizing the solution, filtering solids, then recrystallize the solute by slowly cooling
In the XY2 type, the O···H and X···Y interactions have been assigned between HOY and HC3OX molecules. In the H···O interaction HOY acts as HBD while in the X···Y it might act as electron acceptor (Lewis acid) or electron donor (Lewis base) regarding the nature of X and Y atoms. In the XY3 model a halogen bond (XB) interaction was found between HC3OX and HOY in which Y atom of HOY as electron acceptor interact with O atom of HC3OX as electron donor. It should be noted that no halogen bond was observed between HC3OX and HOF (FF3, ClF3, BrF3 and IF3). The intermolecular distances for complexes and the bond lengths difference between complexes and isolated monomers are listed in Table 1.