Data: Nitration of methyl benzoate: Weight of filler paper: 0.682g Mp product: 76-77 C Nitration of Acetanilide: Weight of filler paper: 0.691g Weight of filler paper product: 1.232g Mp product: 212-214 C Compound MM (g/mol) ortho mp (oC) meta mp (oC) para mp (oC) Nitroacetanilide 180.16 94 155 214-217 Methyl nitrobenzoate 181.15 -13 78-80 94-96 Draw all the resonance forms for the arenium ion formed during the nitration of acetanilide.

Data: Nitration of methyl benzoate: Weight of filler paper: 0.682g Mp product: 76-77 C Nitration of Acetanilide: Weight of filler paper: 0.691g Weight of filler paper product: 1.232g Mp product: 212-214 C Compound MM (g/mol) ortho mp (oC) meta mp (oC) para mp (oC) Nitroacetanilide 180.16 94 155 214-217 Methyl nitrobenzoate 181.15 -13 78-80 94-96 Draw all the resonance forms for the arenium ion formed during the nitration of acetanilide.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.51P

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Data: Nitration of methyl benzoate: Weight of filler paper: 0.682g Mp product: 76-77 C Nitration of Acetanilide: Weight of filler paper: 0.691g Weight of filler paper product: 1.232g Mp product: 212-214 C Compound MM (g/mol) ortho mp (oC) meta mp (oC) para mp (oC) Nitroacetanilide 180.16 94 155 214-217 Methyl nitrobenzoate 181.15 -13 78-80 94-96 Based on the table above , determine the regiochemistry of your nitroacetanilide and draw the structure. Draw all the resonance forms for the arenium ion (cation intermediate) formed during the nitration of methyl benzoate.
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Compound	MM (g/mol)	ortho mp (^oC)	meta mp (^oC)	para mp (^oC)
Nitroacetanilide	180.16	94	155	214-217
Methyl nitrobenzoate	181.15	-13	78-80	94-96