ochem2 lab 2 - Title: Electrophilic Aromatic Substitution:...

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Title: Electrophilic Aromatic Substitution: Nitration of Methyl Benzoate Introduction An electrophilic aromatic substitution will be performed in this experiment; more specifically, nitration of methyl benzoate. In electrophilic aromatic substitutions, an electrophile adds to one of the aromatic ring carbons and generates a resonance stabilized carbocation intermediate. The carbocation eliminates a proton and regenerates the stable aromatic ring. In this experiment, the nitronium ion (NO 2 + ) will act as the electrophile. The nitronium ion can be formed from the reaction of sulfuric and nitric acid: The mechanism for the nitration of methyl benzoate is: After the product is isolated, the percent yield will be calculated and a melting point determination will help discern whether the product is the ortho , meta , or para isomer. Table of Reagents mol. wt. (g/mol) mp (°C) density(g/mL) methyl benzoate 136.15 1.094 sulfuric acid 98.08 1.84 nitric acid 63.01 1.42 methyl o -nitrobenzoate 181.15 -13 methyl m -nitrobenzoate 181.15 78-80 methyl p -nitrobenzoate 181.15 94-96 Safety Information - be careful in handling nitric and sulfuric acid, two strong acids; dispose in appropriate
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ochem2 lab 2 - Title: Electrophilic Aromatic Substitution:...

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