The purpose of this study was to conduct a Diels-Alder reaction with the reactants, anthracene-9-methanol and N-methylmaleimide, in conjunction with the principles and metrics of green chemistry: increasing atom economy, utilizing safer solvents, and preventing pollution.1 Upon completion of the calculation, the atom economy and percent yield were found to be 100% and 4.88% respectively. Subsequently, melting point range analysis yielded a melting range of 218-220℃. These findings could be useful for individuals looking to maximize the percent yield for other Diels-Alder reaction while utilizing benign green reagents and solvents. Introduction:
A Diels-Alder reaction involves a cyclic flow of electrons in a concerted step in which the conjugated diene, supplies 4 pi electrons and the alkene or alkyne, known as the dienophile, supplies 2 pi electrons. In this process, two new sigma bonds, which link the former dienophile to the diene, and one new pi bond, between the former double bonds on the diene, are formed. Furthermore, the reaction can involve molecules with a large variety of substituents, as long as there is a diene with electron donating groups and a dienophile with electron withdrawing groups as this can speed up the reaction. A critical part of the
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Furthermore, the principles and metrics of green chemistry were incorporated into the synthesis reaction through the use of the benign solvent, water. Through the use of the vacuum filtration and the recrystallization procedures, the product was further purified. Subsequently, the purity and identity of the product were evaluated through the analysis tool of Nuclear Magnetic Resonance. Ultimately, the efficiency and greenness of the reaction were measured through the calculation of the percent yield and the atom
This week in lab a Diels-Alder reaction produced 4-cyclohexene-1, 2-dicarboxylic anhydride by combining 1,3 butadiene and maleic anhydride. They reaction basically combined 4 pi electrons from a diene and 2 pi elections from a double bond to produce an alkene ring. The diene must be in s-cis conformation for the reaction to even happen. All of the p-orbitals, both from the diene and the double bond must line up so it can attack from top or bottom, which creates a chair structure. Because of this, the trans conformation is favored due to the lesser steric interactions.
After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some
In our everyday life, we witness many chemical reactions. Some fun reactions you may know about are mentos and pop or vinegar and baking soda. Those two reactions are visible to the naked eye. You aren't able to see photosynthesis completely but you know that it take place because a plant grows. Now what about the chemical reactions that you aren't able to see? How do you know when they are complete? Well let me explain this bright and interesting new discovery.
In this paper, the four Diels-Alder reactions observed in lab will be analyzed in terms of their mechanisms and experimental procedures. Through the Diels-Alder reaction, four different products were formed: dimethyl tetraphenyl phthalate, hexaphenylbenzene, tetraphenylnaphthalene, and triptycene. The general Diels-Alder rules and patterns were followed for each reaction, however, certain things such as solvents and experimental methods were changed in accordance to compounds in order to allow the Diels-Alder reactions to fully and wholly occur.
The dehydration of 2-methyl-2-butanol was performed using sulfuric acid and phosphoric acid in order to synthesize alkene products 2-methyl-1-butene and 2-methyl-2-butene. After carrying out steam distillation to isolate the organic alkenes from aqueous components within the reaction mixture, the purity and characterization of the products were then assessed through various analytical methods including Gas Chromatography (GC), Infrared Radiation (IR) Spectroscopy, and Nuclear Magnetic Resonance (NMR) Imaging. Through the characterization of the final products, it was found that little impurities remained in the final reaction solution and according to the GC, no alcohol remained in the vial after the reaction was complete. The actual yield
5 points Name 5 and only 5 ways to make the synthesis of a pharmaceutical compound more green that are presented on the poster.
For this experiment, a dehydrobromination was performed on a meso-stilbene dibromide to form an alkyne. The meso-dibromostilbene was converted into diphenylacetylene, an alkyne, through two E2 elimination reactions. The dibromostilbene reacted with a strong base, potassium hydroxide, at a very high temperature. The hydroxide, from KOH, deprotonated one of the aliphatic hydrogen atoms or protons which formed an alkene and broke one of the C-Br bonds releasing the bromine. This process does not take much energy to remove one of the H-Br. This process was completed twice, and the second C-Br bond was broken, and an alkyne formed. This process was more difficult due to the rotation needed to perform the initial elimination. The elevated temperature
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
In a Diels-Alder [4+2] cycloaddition reaction the conjugated diene and dienophile solvent (toluene, xylene) had a high boiling point that resulted in a six-membered ring with two σ-bonds and a newly formed π-bond (Scheme1)
The purpose of this lab is to observe the changes in a chemical reaction and how factors affect the system like increase concentrations, temperature, pressure or common ions affect the outcome of the overall reaction and its equilibrium. The Le Chatelier's Principle is used often in order to determine the direction of a reaction, like a balance when disturbed it shifts to more over to one side than the other; in this case if one side of the reaction is stressed the other side will react to counteract for the change. This often means that more or less products will form or reactants will be more present in the end. The five stages performed in this lab with varying chemicals each with stressed the system in various ways. The first reaction is
In this lab, the study of the kinetics of a chemical reaction will be investigated. One of these reactions involved the oxidation of iodide ions by bromate ions in the presence of an acid.
The objective of this experiment was to find the mole ratios of the reactants and products for the chemical reaction, without being given the products.
The rate law of a chemical reaction is a very useful equation that relates the concentration of reactants to time. The law was formed from the results of experiments by various European chemists throughout the second half of the 1800s, when they caught on that there was a correlation between the concentration of reactants and time. The most basic formula of the equation is Rate=k[A]n[B]m..., where Rate is the rate of the reaction in concentration per second (M/s), k is a constant, [A] and [B] are the concentrations of the reactants (M), and n and m are values that rate to the order of each reactant. All the values in the equation can be determined experimentally by taking the concentrations of reactants and the corresponding rate at multiple
The Grignard reactions cannot be classified as nucleophilic substitutions, even though the reactions are clearly substitution reactions. The functional carbon atom was reduced, resulting in the polarity of functional group being inverted; an electrophilic carbon became a nucleophilic carbon. This resulted in the alkyl halide and the Grignard reagents being excellent nucleophiles. The basic reaction of the Grignard reaction involves the nucleophilic attack of the carbanionic carbon in the organometallic reagent to the electrophilic carbon in the carbonyl to form
In practice, the most prominent product that is formed is the meso¬-stilbene dibromide. The experiment will focus on attempting to isolate meso-stilbene dibromide from the product mixture also containing dl-stilbene dibromide diastereomers. The success of this isolation will be measured by the melting point for purity reasons, and the percent yield of the product. Alkenes are quite reactive molecules due to their polarizable carbon to carbon pi bond. Addition reactions across a pi bond are common due to the fact that pi bonds are weaker than sigma bonds, at 60-65 kcal/mol and 80-100 kcal/mol respectively.