Nitration of methyl benzoate lab report. Nitration of methyl benzoate Report 2022-12-13

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Nitration of methyl benzoate is a common laboratory experiment that is used to demonstrate the principles of electrophilic substitution reactions. In this reaction, methyl benzoate, a carbonyl compound, is converted into the corresponding nitro compound, nitro methyl benzoate, through the addition of a nitro group.

The reaction begins by mixing concentrated sulfuric acid with a small amount of nitrating agent, typically nitric acid. The sulfuric acid acts as a protonated catalyst, increasing the electrophilicity of the nitric acid and facilitating the attack of the nitro group on the double bond of the methyl benzoate.

After the reaction mixture has been stirred for a period of time, typically several hours, the product is isolated by adding the mixture to a large excess of cold water. The nitro methyl benzoate will crystallize out of solution, while the excess sulfuric acid and nitric acid will remain in the aqueous phase. The product can then be collected by filtration and dried.

One of the key features of the nitration of methyl benzoate is the regioselectivity of the reaction. The nitro group has a strong preference for attaching to the para position of the benzene ring, rather than the meta or ortho positions. This preference is due to the resonance stabilization of the intermediate species that is formed during the reaction.

The yield of the nitration of methyl benzoate can also be influenced by several factors, including the concentration of the reactants, the temperature of the reaction, and the presence of any solvents or catalysts. By carefully controlling these variables, it is possible to optimize the yield of the reaction and produce a high-quality product.

Overall, the nitration of methyl benzoate is a valuable laboratory experiment for demonstrating the principles of electrophilic substitution reactions and the factors that can influence the yield and regioselectivity of such reactions.

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Nitration of methyl benzoate is a common laboratory experiment in undergraduate chemistry courses. It involves the reaction of methyl benzoate, a compound with a benzene ring and a methyl group attached, with nitric acid and sulfuric acid to form nitro methyl benzoate. This reaction is an example of an electrophilic substitution reaction, where the nitronium ion (NO2+) acts as the electrophile and the benzene ring of the methyl benzoate acts as the nucleophile.

The experiment begins by preparing a solution of nitric acid and sulfuric acid, known as "nitrating mixture." The nitrating mixture is typically prepared by carefully measuring out equal volumes of concentrated nitric acid and sulfuric acid and mixing them together. It is important to be cautious when handling these strong acids, as they can cause serious burns and are toxic if ingested.

Next, the methyl benzoate is added to the nitrating mixture and the reaction is allowed to proceed. The reaction typically occurs at room temperature, but it can be facilitated by heating the mixture. As the reaction proceeds, the nitronium ion attacks the benzene ring of the methyl benzoate, forming a nitro group and a carbocation intermediate. The intermediate is then stabilized by the methyl group, resulting in the formation of nitro methyl benzoate.

During the reaction, it is important to monitor the progress of the reaction using thin layer chromatography (TLC). TLC is a separation technique that allows for the identification and quantification of the various products formed during the reaction. By comparing the Rf values (a measure of the movement of a compound on the TLC plate) of the products to standards, the percentage yield of the nitro methyl benzoate can be determined.

Once the reaction is complete, the nitro methyl benzoate is typically purified by recrystallization. This involves dissolving the product in a solvent and allowing it to slowly crystallize out as the solution cools. The purified product is then collected, weighed, and analyzed using infrared spectroscopy to confirm the presence of the nitro group.

In conclusion, the nitration of methyl benzoate is a useful laboratory experiment that allows students to understand the mechanisms of electrophilic substitution reactions and the use of TLC for product analysis. It is important to be cautious when handling the strong acids used in the reaction and to follow proper safety protocols in the laboratory.

Nitration Of Methyl Benzoate Report Example (500 Words)

nitration of methyl benzoate lab report

Aromatic rings are nitrated, sulfonated, halogenated, alkylated, and ocellated using the zirconium ion, NO2+, in a solution of mixed nitric and sulfuric acids. The HNO3 and H2SO4 were combined to form a nitrating solution, which was mixed with a mixture of methyl benzoate and H2SO4. The role of the nucleophile is played by the double bond on the benzene ring. After filtration, the product is recrystallized from methanol. .

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Nitration of methyl benzoate lab report

nitration of methyl benzoate lab report

The flask was removed from the plate and left to cool to room temperature before beginning. What would you expect the structure of the dinitro ester to be? With additional reactions with a base, the electrophile fundamentally replaces the hydrogen of the benzene. The benzene of the reactant methyl benzoate is deactivated by an ester in the —COOCH3 substituent, suggesting that the nitro group adds only to a meta position within the ring and forms methyl m-nitrobenzoate see Figure 1. This value was discovered by the initial amount of the reactants used: 0. The IR test was performed. Nitration of Methyl Benzoate Date of Completion: February 29, 2012 Date Report Submitted: March 14, 2012 Objective of Experiment: The purpose of this experiment is was to synthesize methyl 3-nitro benzoate from methyl benzoate through an electrophilic aromatic substitution reaction.

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Nitration Of Methyl Benzoate Lab Report

nitration of methyl benzoate lab report

Although this may cause a higher calculated recovery, the value would not be accurate to the experiment. The limiting reactant in the reaction, benzoin + nitric acid benzil, was benzoin at 0. Organic Chemistry PURPOSE The purpose of this experiment was to complete the nitration of methyl benzoate by making a substitution reaction with the nitronium ion made from the reaction between nitric and sulfuric acid. This product is going to waste, and our objective is to see if we can obtain a usable end product when reacting m-aminobenzoic acid with 2,4-dinitrochlorobenzene. Other functional groups, such -COOH, -NO2, and -SO3H, take electrons away from the ring, rendering it "inactive," and instead direct into the meta locations. The crystals reappeared when cooled down in the ice bath. Some of the loss of product could be due to the constant transfer of the solution.

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Lab Report

nitration of methyl benzoate lab report

The sulfuric acid protonates the nitric acid to generate the necessary electrophile. The final product was m- 2,4-dinitroanilino benzoic acid. This reaction consists usually of benzene and an electrophile. Consider the directing effects of the ester and the first nitro group upon the addition of the second nitro Lab 6: Electrophilic Aromatic Substitution Lab 6: Electrophilic Aromatic Substitution 1 Nitration of Methyl Benzoate 2 Synthesis of 1,4-Di-t-butyl-2,5-dimethoxybenzene byFriedel-Crafts Alkylation of 1,4-DimethoxybenzenePurpose1 To carry out the nitration of methyl benzoate, and then identify the major product formed position at which nitro-group substitution takes place by thin-layer chromatography TLC , the percent yield and the melting point range. The order in which reactions are performed plays an important role in the changing reactive properties of the molecule: substituting a particular functional group onto benzene will not only change the molecular structure, but it also affects the reactivity of the ring and potentially removes the possibility of certain reactions. Retrieval of methyl m-nitrobenzene To further separate the products I used a modified recrystallization technique wherein an equal mass of methanol was combined with the entirety of the crude product in a new 25mL Erlenmeyer flask.

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Nitration of methyl benzoate Report

nitration of methyl benzoate lab report

The intermediate arenium ion would have a sigma complex containing four resonance structures. The purpose of this experiment was to prepare the student to the real world by them designing their own procedure which will help them understand the techniques of separation and purification better. Percent yield for the final product was calculated followed by recrystallization and melting point was measured. 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. The electrophilic aromatic substitution reaction nitration is used to nitrate methyl benzoate and acetanilide with a nitronium ion.


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Nitration_of_methyl_Benzoate_Lab_Report

nitration of methyl benzoate lab report

Separation of crude product The contents of the 25mL Erlenmeyer flask were then poured over ~25g of crushed ice in a 150mL beaker. Benzene is classified as one of the countless aromatic molecules, and this is just a plain benzene molecule. In this experiment, we also learned how to set up a chemical reaction for the nitration of aromatic compounds, using nitric acid and sulfuric acid. Crystallization was used to purify the product. The resultant solution was heated, mixed with deionized H2O and vacuum filtrated in order to separate our formed product form the solvent.

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Nitration of Methyl Benzoate Lab blog.sigma-systems.com

nitration of methyl benzoate lab report

After the ice had melted completely, the product was isolated by using vacuum filtration with a Büchner funnel. INTRODUCTION: Compounds containing benzene are known to have unique characteristics that cause them to react differently from other molecules. The order in which reactions are carried out is crucial in determining how the reactive properties of the molecule change. Remark Sulfuric acid H 2 SO 4 98. Nitration of Methyl Benzoate Introduction: Most aromatic rings are unreactive and stable.

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Nitration of Methyl Benzoate lab report

nitration of methyl benzoate lab report

Conclusion With the completion of the experiment, the very low yield was calculated providing a high percent error. Substitution para to the acetamido group is favored over substitution ortho to that group, because the great bulk of the acetamido group shields the ortho positions from approach by reagents. Hydrocarbons do not dissolve in concentrated sulfuric acid, but methyl benzoate does. Most of them are found in mixtures and in order to achieve a pure form they need to be separated, isolated, and purified. Hydrocarbons do not dissolve in concentrated sulfuric acid because hydrocarbons are non polar.


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nitration of methyl benzoate lab report

Using a Pasteur pipet, the sulfuric acid and nitric acid mixture was added dropwise to the sulfuric acid with methyl benzoate mixture. This steric hindrance makes ortho substitution much less likely than para substitution, in which the bulk of the acetamido group has no influence. This combination resulted in a clear yellow liquid. A more powerful electrophile is required to complete the substitution. The melting point was used to determine its purity and the regiochemistry of the products. The nitronium ion is generated due to a reaction that takes place between the concentrated nitric acid and sulfuric acid. This technique was further repeated after our product was washed with heated ethanol.

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