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Nitration of Methyl Benzoate

Nitration of Methyl Benzoate. Multistep Synthesis. 50%. 50%. C. B. A. Yield =. 25%. Ortho Meta Para. Ortho. Meta. Para. Number Ring. 6. 2. 3. 5. 4. Nucleophilic Aliphatic Substitution. Electrophilic Aromatic Substitution. ARENE SUBSTITUTION. E +. + H +.

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Nitration of Methyl Benzoate

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  1. Nitration of Methyl Benzoate

  2. Multistep Synthesis 50% 50% C B A Yield = 25%

  3. Ortho Meta Para Ortho Meta Para

  4. Number Ring 6 2 3 5 4

  5. Nucleophilic Aliphatic Substitution Electrophilic Aromatic Substitution

  6. ARENE SUBSTITUTION E+ + H+ The electrophile REPLACES H+

  7. Mechanism E - Y

  8. E - Y Mechanism + H+

  9. Charge o and p

  10. Energy Diagram

  11. Nitration of Benzene Nitrobenzene

  12. Nitration Reagent HONO2 + 2 H2SO4 NO2+ + H3O+ + 2 HSO4- Nitronium Ion

  13. Nitration Mechanism

  14. Multiple Substituents G Second Group. Where go? How fast?

  15. Nitration of Toluene HNO3 63% 3% 34%

  16. ORTHO Compare o, m, p + + + META + + + PARA + + +

  17. Electron Donating Groups Favor: ORTHO and PARA. Electron Donating Ortho Para

  18. Nitration of trifluoromethylbenzene HNO3 H2SO4 6% 91% 3%

  19. Electron Withdrawing Groups + charge here bad

  20. Ortho Compare o, m, p + + + Meta + + + Para + + +

  21. Electron Withdrawing Groups Meta Directors and DEACTIVATING Electron Withdrawing Group Meta Product

  22. Ortho-Para Directors Very Activating -NH2 -NHR -OH -OR O -NHCR O -OCR

  23. Ortho-Para Directors Activating -R Activating -Ar Deactivating -Halogens

  24. Meta Directors O -SO3H -CR O -NO2 -COH -CN

  25. Main Reaction meta Side Products

  26. Procedure 1. Dissolve methyl benzoate in H2SO4 2. Mix HNO3 and H2SO4 at 0oC 3. Add HNO3 / H2SO4 dropwise to methyl benzoate at 0oC

  27. Procedure 4. Let stand at room temperature 10 minutes 5. Pour onto ice

  28. Filter

  29. Wash Recrystallize from methanol Dry Weigh m.p.

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