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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.
E N D
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+
Nitration of Benzene Nitrobenzene
Nitration Reagent HONO2 + 2 H2SO4 NO2+ + H3O+ + 2 HSO4- Nitronium Ion
Multiple Substituents G Second Group. Where go? How fast?
Nitration of Toluene HNO3 63% 3% 34%
ORTHO + + + META + + + PARA + + +
Electron donating groups favor reaction ORTHO and PARA. Electron Donating Ortho Para
Nitration of (trifluoromethyl)benzene HNO3 H2SO4 6% 91% 3%
Electron Withdrawing group + charge here bad
Ortho + + + Meta + + + Para + + +
Electron Withdrawing Groups are Meta Directors and DEACTIVATING Electron Withdrawing Group Meta Product
Main Reaction meta
Procedure 1. Dissolve methyl benzoate in H2SO4 2. Mix HNO3 and H2SO4 at 0oC 3. Add HNO3 / H2SO4 dropwise to methyl benzoate at 0oC
4. Let stand at room temperature 10 minutes 5. Pour onto ice
Wash Recrystallize from methanol Dry Weigh m.p.
