Preparation of methyl m-nitrobenzoate by nitration using methyl benzoate, nitric acid, and sulfuric acid solution

Aileen Quintana

TA: Sijie

Tues/Thurs 14: 50

42067

Introduction:

The purpose of this lab was going to explore the concepts of electrophilic aromatic substitution, specifically nitration simply by synthesizing methyl m-nitrobenzoate employing methyl benzoate, nitric chemical p and sulfuric acid. This kind of nitration is actually a type of electrophilic aromatic substitution. A firmly charged electrophile, in this case a nitro group, replaces a proton for the aromatic engagement ring. Aromatic compounds undergo alternative instead of conjunction with maintain resonance. The substituent on the benzene ring establishes where the electrophile will add. Electron pulling out substituents, like nitro group, withdraw bad particals due to induction and immediate position of the carbocation through resonance to add electrophile to meta situation. Nitric acidity, sulfuric acid solution, and methyl benzoate will probably be mixed and added to a great ice bathtub. Crushed ice will probably be added to this frosty mixture and form deposits. В After amazingly product of m-methylbenzoate forms and purifies through recrystallization, its MP and VENTOSEAR will be delivered to test purity and confirm predicted position of the nitro group. Excess weight of final product will be in comparison to crude weight to determine performance of treatment. It is possible to obtain small amounts of ortho and para isomers of nitrobenzoate and dinitration products. These will be taken off when method washed in methanol and purified. Glaciers added will probably be minimal since excess remise nitration simply by interfering with all the nitric acid-sulfuric acid equilibria. The higher the temperature, the higher dinitration items formed. Seeing that only one nitro group is usually desired, temperatures should be taken care of low to stop dinitration (15 C ). The formation in the electrophile:

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The system:

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Info and Computations:

Table one particular provides the shedding point and...