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Tema 1.9 Session3
 

Tema 1.9 Session3

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    Tema 1.9 Session3 Tema 1.9 Session3 Presentation Transcript

    • Mòdul MD2301 - Formació general; 564497 – Química orgànica i inorgànica MASTER ON DRUGS, COSMETICS AND FOOD QUALITY Dr. Antonio Delgado Universitat de Barcelona October 2009
    • Session 3 Electrophilic aromatic substitution . Benzene, substituted benzenes and their reactivity with electrophiles. Directing groups. Organic synthesis . Linear versus convergent synthesis. Protecting groups in organic synthesis. Retrosynthetic analysis. Enantiopure compounds: chemical resolution of racemates.
    • Hückel’s rule : (4n+2)  electrons delocalized (conjugated) in a cyclic system Electrophilic aromatic substitution
    • Heterocyclic aromatic systems
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    • Stability of aromatic systems
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    • Electrophilic aromatic substitution Halogenation
    • Electrophilic aromatic substitution Nitration
    • Electrophilic aromatic substitution Sulfonation
    • Electrophilic aromatic substitution Alkylation
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    • Electrophilic aromatic substitution
    • Electrophilic aromatic substitution on benzene derivatives
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      • Construction of the carbon skeleton
      • Functional group transformations
      • Functional group protection
      • Stereochemical control (stereogenic centers)
      Planning an organic synthesis Basic steps
    • Planning an organic synthesis Construction of the carbon skeleton Linear vs convergent synthesis Linear synthesis Convergent synthesis
    • Construction of the carbon skeleton Retrosynthetic analysis: Strategic disconnections and synthon generation Reagent Real species Synthon ( “virtual”) Ionic or radical fragment arising from a disconnection
    • Equivalence between synthons and reagents
    • Functional group transformation Reduction of carbonyl derivatives
    • Functional group protection: protecting groups in peptide synthesis: Reactivity control
    • Protecting groups in peptide synthesis Directionality in peptide bond formation
    • Stereochemical control Enantiomers and chirality
    • Enantiomers can show different biological activity
    • Resolution of racemic mixtures Chiral chromatography
    • Chemical resolution (diastereomeric salt formation)
    • An example of diastereomeric salt formation
    • Resolution of racemic mixtures Diastereomeric salt formation in “high throughput format”
    • Resolution of racemic mixtures Chiral chromatography