Nitration of Methyl Benzoate

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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 +. - PowerPoint PPT Presentation

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  • Nitration of Methyl Benzoate

  • Multistep SynthesisABC50%50%Yield = 25%

  • Ortho Meta ParaOrthoMetaPara

  • Number Ring23456

  • Electrophilic Aromatic SubstitutionNucleophilic Aliphatic Substitution

  • ARENE SUBSTITUTION

    E++ H+The electrophile REPLACES H+

  • MechanismE - Y

  • Mechanism E - Y+ H+

  • Charge o and p

  • Energy Diagram

  • Nitration of BenzeneNitrobenzene

  • Nitration ReagentNitronium IonHONO2 + 2 H2SO4NO2+ + H3O+ + 2 HSO4-

  • Nitration Mechanism

  • Multiple Substituents

    GSecond Group. Where go? How fast?

  • Nitration of TolueneHNO363%3%34%

  • Compare o, m, p+++++++++ORTHOMETAPARA

  • Electron Donating GroupsFavor: ORTHO and PARA.Electron DonatingOrtho Para

  • Nitration of trifluoromethylbenzeneHNO3H2SO46%91%3%

  • Electron Withdrawing Groups+ charge here bad

  • Compare o, m, pOrthoMetaPara+++++++++

  • Electron Withdrawing GroupsMeta Directors and DEACTIVATINGElectronWithdrawing GroupMeta Product

  • Ortho-Para Directors-NH2-OH-NHR-OR-OCR-NHCROOVery Activating

  • Ortho-Para Directors-R-Ar-HalogensActivatingActivatingDeactivating

  • Meta Directors

    -CRO-COHO-CN-SO3H-NO2

  • Main ReactionSide Productsmeta

  • Procedure1. Dissolve methyl benzoate in H2SO42. Mix HNO3 and H2SO4 at 0oC 3. Add HNO3 / H2SO4 dropwise to methyl benzoate at 0oC

  • Procedure4. Let stand at roomtemperature 10 minutes

    5. Pour onto ice

  • Filter

  • Wash

    Recrystallize frommethanol

    Dry

    Weigh

    m.p.

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