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Nitration of Methyl Benzoate

Nitration of Methyl Benzoate. Multistep Synthesis. 50%. 50%. C. B. A. Yield =. 25%. Nucleophilic Aliphatic Substitution. Electrophilic Aromatic Substitution. ARENE SUBSTITUTION. E +. + H +. The electrophile REPLACES H +. E - Y. + H +. Charge o and p. Nitration of Benzene.

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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. Nucleophilic Aliphatic Substitution Electrophilic Aromatic Substitution

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

  5. E - Y + H+

  6. Charge o and p

  7. Nitration of Benzene Nitrobenzene

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

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

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

  11. ORTHO + + + META + + + PARA + + +

  12. Electron donating groups favor reaction ORTHO and PARA. Electron Donating Ortho Para

  13. Nitration of (trifluoromethyl)benzene HNO3 H2SO4 6% 91% 3%

  14. Electron Withdrawing group + charge here bad

  15. Ortho + + + Meta + + + Para + + +

  16. Electron Withdrawing Groups are Meta Directors and DEACTIVATING Electron Withdrawing Group Meta Product

  17. Main Reaction meta

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

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

  20. Filter

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

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