Lewis-Acid Catalyzed electrophilic aromatic substitution reactions of thionyl chloride, and benzene. Introduction: Organic sulfoxides, especially diphenyl sulfoxide (Ph2SO), are useful synthetic reagents (Kaczorowska et al., p. 8315). Diphenyl sulfoxide has been used in catalytic oxidation of alkyl sulfides to sulfoxides (Arterburn & Nelson, p.2260). They also play an important role as therapeutic agents. Examples include anti-ulcer, antibacterial, antifungal, anti-therosclerotic, anthelmintic, antihypertensive, and cardiotonic agents, as well as, psychotonics and vasodilators (Kaczorowska et al., p. 8315). Diphenyl sulfoxide is also used as a reagent in the formation of glycosidic bonds (Garcia, Pool, & Gin, p.1). This involves an in situ …show more content…
This difference can lead to differing yields in the products of interest. In this case, what is to be determined is which Lewis-acid catalyst produces higher yields of diphenyl sulfoxides. Previously, aluminum-chloride-catalyzed Friedel-Crafts (EAS) reactions of thionyl chloride (SOCl2) with benzene (PhH) were conducted. Thionyl chloride readily combines with AlCl3 to produce diphenyl sulfoxide, mainly when mixed in 2:1:1 molar ratio (Sun, Haas, McWilliams, Smith, & Leaptrot, p.1). Thionyl chloride and aluminum chloride combine via a OAl coordination bond forming 1:1 zwitterionic adduct Cl2SO+--AlCl3 (Sun, Haas, Sayre, & Weller, p.1). What has not been performed yet is a similar reaction involving iron(III) chloride (FeCl3). The FeCl3-catalysed Friedel-Crafts (EAS) reactions with thionyl chloride and benzene will optimistically produce different yield percentages of diphenyl sulfoxides and diphenyl sulfides than that of the AlCl3-catalysed reactions. Hopefully, the study of these reactions will lead to better knowledge of how Lewis-acid catalysts play a role in electrophilic aromatic substitution reactions. The reactions will be performed at various temperatures (-10°C, 0°C, 25°C,45°C, 70°C) and have differing mole ratios (2:1:1, 3:1:1), which will produce dissimilar product yields. The reagents will also be mixed in various ways, and the purpose of this is to see which order of mixing …show more content…
8315). Furthermore, the organic sulfoxides have an important function as therapeutic agents and these include: anti-ulcer, antibacterial, antifungal, and cardiotonic agents, as well as, psychotonics and vasodilators (Kaczorowska et al., p.8315). Examining these various reactions, which produce sulfoxides, will be important for educational purposes: providing alternate ways to obtain sulfoxides, and to distribute more knowledge on Lewis-Acid catalysts and their interaction in EAS reactions. Lewis-acids are an important class of acids and are imperative for adolescents and even adults, who are in schooling, to learn
The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.
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.
This experiment was designed by conducting a substitution reaction to construct a complex compound (2-methylphenoxyacetic acid) from two simple parts; also known as synthesis - converting simple molecules into more complex molecules. A purification technique known as crystallization was used to purify the product. Suction filtration was used to filter out the product. The experiment was completed over a three-day experimental period.
The antibacterial effects of sulfanilamide were first observed in 1932, when German bacteriologist and pathologist Gerhard Domagk noted the effects of the red dye Prontosil on Streptococcus infections in mice. It was later proved by French researchers that the active agent of Prontosil was sulfanilamide, or para-aminobenzenesulfonamide, a product of the body’s metabolism of Prontosil. By the 1940s sulfanilamide was a widely used drug. During World War II white sulfanilamide powders became standard in first-aid kits for the treatment of open wounds, and sulfanilamide tablets were taken to fight intestinal infections. Though the medicine was relatively safe, allergic reactions such as skin rashes, fever, nausea, vomiting, and even mental confusion
The reactivity and regioselectivity of 1,3-dipolar cycloaddition reactions of 3-azidopropane-1,2-diol (1) with diacetylene derivatives (2a, 2b and 2c) have been investigated by using density functional theory (DFT) -based on reactivity indices and activation energy calculations at B3LYP/6-31G(d) level of theory in the gas phase. The potential energy surface analyses for both reactions are in agreement with the experimental observations. Moreover, our calculations on the geometries, bond orders (BOs) and charge transfers (CTs) at the transition state (TS) structures shows which these 1,3-DC reactions occur via an synchronous concerted mechanism, and unfavorable TSs are more asynchronous than the favorable
Introduction: The formation of sp2 carbons can be difficult at times because of different reaction environments can cause different outcomes of the product, which generally yields impure products or the wrong products. However, by turning the reagent into a Grignard reagent, it is possible to get a SN2 like reaction to occur most of the time which helps in the formation of certain industrial and pharmaceutical compounds. The Grignard reaction allows sp2 carbons to react with losing its hybridization, and allows carbon chains to be extended while also adding an alcohol functional group, which can be useful as seen when producing selective alcohols. This can be seen in this experiment as the formation of Malachite green, being a dye, or with
If the results of these tests show that there is no change is mouse behavior or tissue degeneration of the brain, then Huntington’s disease did not affect the mice. This might be caused by a loss of cell-tissue or failed gene introduction within the brain of the mice, which has been observed while using electroporation. This problem occurs due to the amount of voltage added to the injection site, which varies depending on the experiment. For this experiment, a low voltage is used, which can ensure the health of the mouse, but not always full introduction of the new gene. Higher voltages can be used to ensure the full introduction of the new gene, but they also cause more cell death within the mice, (De Vry).
Introduction An organic reaction of aromatic compounds in which a positive ion or other electron-deficient species with a full or large partial positive charge known as an electrophile replaces a hydrogen bonded to a carbon of an aromatic ring is known as an electrophilic aromatic substitution reaction. This reaction is very important for aromatic compounds allowing the direct introduction of groups placements and providing synthetic routes to many important compounds.1 Aromatic rings like benzene are susceptible to electrophilic attacks but rather than addition reactions they undergo substitution reactions. Substitution reactions allow the pi electrons in benzene to regenerate after being attacked by the electrophile.1 In step one of an electrophilic aromatic substitution reaction, an attack of the electrophile by a pi bond of the aromatic ring occurs. The electrophile takes two electrons of the aromatic system to form a sigma bond to one carbon atom of the benzene ring.
For this purpose, to optimize the reaction conditions for the synthesis of compound 3a, the condensation reaction of benzaldehyde (1 mmol) and 2-naphthol (2 mmol) was test using different amounts of silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride as a Brønsted acid ionic liquid catalyst under solvent- and metal-free conditions at ambient temperature (Table 1). As it can be seen in Table 1, when reaction was carried out in the absence of the silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride, after 120 minute the reaction was without yield of product (Table 1, entry 1). The best results were achieved when 20 mol% of the silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride was appropriate to promote the
The hypothesis that as the level from which the electron jumps is increase, the emitted frequency would also increase, was supported in this lab. As the level of the electron was increased, the emitted frequency increased in a manner that was indirectly linear to the of the level of the electron. The accuracy in this lab was excellent with a 2% and 1% error for the hydrogen gas portion. The accuracy for the measurement of the measure of the wavelengths of two colors in the helium gas was also excellent with percent errors of 2.7% and 2.9%. A potential systematic error in this lab could have been incorrectly measuring the distance from the diffraction grating to the gas tube. This would cause every calculated wavelength to either be larger
If genetic transformation allows the insertion of a gene into an organism to gain the trait that the inserted gene codes for, then when 250 µl of transformation solution(CaCl2) and 2-4 colonies of bacteria, E. coli, are added to two micro test tubes, labelled +pGLO and –pGLO, with a loopful of pGLO DNA solution in the +pGLO tube, and are incubated for 10 minutes, then transferred to a 42ºC heat bath for exactly 50 seconds, and then incubated in ice again for 2 minutes for a heat shock, and then have 250 µl of LB nutrient broth, and lastly 100 µl of the solutions spread across the surfaces of 4 LB nutrient agar plates, LB/amp, LB/amp/ara, LB/amp, and LB, with +pGLO, +pGLO, –pGLO, and –pGLO used, respectively, the plates with the –pGLO solution will not glow under a UV light after they have
b. Chlorobenzene- is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
In the view of the aforementioned remarked values of inhibition efficiency of this class of organic inhibitors, this paper aims to study the concerned function of the first utilized Schiff bases 3a-k towards mild steel in 0.5 M H2SO4 solution. N-aryl- (Sb_a-g), N-heteryl- (Sb_h-j)-, and the Schiff base Sb_k have been obtained condensation of N-aminophthalimide (S) with the corresponding aromatic aldehydes 2a-e, heterylaldehydes 2f-j and isatine 2k, respectively. This study takes into account the beneficial role that could be played by the p-electrons of the heterocyclic aldehyde or ketone N- and O- atoms present in the heterocyclic aldehyde and ketone moieties. The name of products and symbols were listed in Table 2. The melting point, yield, time of reaction and IR spectra of products were listed in Table 3. Spectral study has been used to characterize the structure of the novel synthesized Schiff bases (Sb_f-k) which to our knowledge have not been previously reported as shown in Table 4. The structure of the Schiff bases Sb_a-e was confirmed by identity of melting point and spectral data in the literature 25-27. The infrared spectra all the products Sb_a-k revealed that no coupling bonds in the 3 Mm region that refers to the absence of the amino –NH2 functionality of compound S instead a sharp absorption band appears on the region of 1604-1688 cm-1. Characteristic to the imino –c=N- group, indicating that compound
Forming C-C bonds at the C2 of azoles is a necessary step in the beginning of the current azole synthesis method which generally requires using strong bases, low temperatures, and/or expensive, toxic precious metal catalysts.5,6,7 By substituting these issues with organic solvents, ambient temperature, and weaker bases, a synthesis method better suited for pharmaceutical industries is created.
Technically, water is considered as the universal solvent in Nature. However, the prevalent notion among today’s chemists is that water is often forgotten in organic synthesis; many considerations are taken in the process of selecting solvents, reagents, and conditions which are water-free. In addition to the obvious problem that concerns about the surrounding water-sensitive reactants, the main problem is solubility which is the requirement for reactions to occur, and it is a justification for the use of many organic solvents at the exclusion of anything else in organic synthesis. Nevertheless, many living biochemical reactions mostly happen in an aqueous medium. The concern about environment and safety is another reason that has flamed up the interest in Green Chemistry, which prompted more researches into alternatives to traditional organic solvents. Therefore, water is a very promising candidate for the future choice of solvent as it is cheap, reusable, nonvolatile and safe to handling of exothermic or heat-releasing reactions. Even though water has many advantages in organic synthesis, the low solubility of organics reagents has prevented the expanding utilization of water as a standard solvent.