to form Methyl-m-nitrobenzoate via Aromatic Substitution Linh Ngoc Thuy Nguyen Seattle Central Community College Professor: Dr. Esmaeel Naeemi Date: February 21st‚ 2012 Abstract In this experiment‚ methyl-m-nitrobenzoate‚ followed the electrophilic addition of aromatic ring‚ would be formed from the starting material methyl benzoate and nitric acid‚ under the catalysis of concentrated sulfuric acid. The reaction between nitric acid and sulfuric acid resulted in the formation of nitronium
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TA: Sijie Tues/Thurs 11:50 42067 Introduction: The purpose of this lab was to explore the concepts of electrophilic aromatic substitution‚ specifically nitration by synthesizing methyl m-nitrobenzoate using methyl benzoate‚ nitric acid and sulfuric acid. This nitration is a type of electrophilic aromatic substitution. A strongly charged electrophile‚ in this case a nitro group‚ replaces a proton on the aromatic ring. Aromatic compounds undergo substitution
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activating effect of aniline‚ phenol‚ anisole and acetanilide after reacting with pyridinum tribromide in order to undergo electrophilic aromatic substitution. The melting point of the isolated products were measured against the standards in order to determine how strong of an ortho/para activator the compound was based on the product(s) and melting point obtained. Theory: Electrophilic aromatic substitution is an organic reaction that takes place when an atom that is bound to an aromatic ring is replaced
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Electrophilic Aromatic Substitution: The Nitration of Toluene Abstract This industrially important reaction of EAS: The Nitration of Toluene exhibits how the attack of a nitronium ion would give out major and minor products at different positions of toluene. This is an electrophilic substitution mechanism. Mixture of concentrated sulphuric and nitric acid will produce a nitronium ion‚ which will attack ortho-‚ meta- and para- positions at Toluene. (Mechanism at appendix). Introduction/Procedure
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favorable because of the presence of two methoxy groups. The groups act as activators to electrophilic aromatic substitution because of their ability to donate electrons through resonance. This enhanced activation helps favor the initial substitution. After this‚ the ring has two methoxy groups and an alkyl group attached to it. The addition of the alkyl group further activate the ring for another electrophilic aromatic substitution. The addition of a second alkyl group must attach on the opposite
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Nitration and Purification of Bromobenzene Abstract: An electrophilic aromatic substitution reaction was performed on bromobenzene with nitric acid producing both 2-bromonitrobenzene and 4-bromonitrobenzene. Products of the reaction were purified through multiple recrystallizations and column chromatography creating multiple crops of a yellow powder. The percent yield of products was determined to be 51%. The melting point of Crop 1 was found to be 110-115 °C‚ and Crop 2 was found to be 37-90
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Experiment #1 – Aromatic Nitration The purpose of this lab is to convert toluene to nitrotoluene through the process of aromatic nitration. This is done by electrophilic aromatic substitution. The aromatic organic compound‚ toluene‚ is reacted under mild conditions with an electrophile‚ the nitronium ion‚ resulting in a product of nitrotoluene. Failure to use mild conditions may result in polynitration. Different reaction conditions were studied to understand the effect of nitrating agent
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The characteristic colors of porphyrins is also due to the conjugation. An examination of the porphyrin structure reveals that individual pyrrole units comprise the overall structure. As an aromatic compound‚ pyrrole can participate in electrophilic aromatic substitution reactions to form the porphyrin (your report should discuss the mechanism in great detail‚ including the regiochemistry). The initial porphyrinogen product is not fully aromatic‚ but oxidation from atmospheric oxygen in the
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Title: Experiment 28: Nitration of Methyl Benzoate Objective: The students will learn to nitrate methyl benzoate through electrophilic aromatic substitution reaction. They will learn the importance of regiochemistry in chemical reactions. They might experience disubstitution through a high temperature. Reactions: Observation: The crystals started to form when added 2 g of crushed ice. The addition of hot methanol dissociated the crystals. The crystals reappeared when cooled down in
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Results:  Figure 5: NMR of the product  Discussion/Conclusion: The melting point of the recrystallized product was 73-78 degrees Celsius. This was very accurate to that of the book. In this experiment‚ methyl benzoate went through an electrophilic substitution reaction to form Mehyl-m-nitro benzoate‚ where a NO2 group was added to the methyl benzoate in the meta position. Nitric acid is not a
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