Tema 1.9 Session3
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The document discusses various topics in organic chemistry including: 1) Electrophilic aromatic substitution reactions like halogenation, nitration, and sulfonation on benzene and substituted benzenes. 2) Factors that influence the reactivity and orientation of electrophilic aromatic substitution, including directing groups. 3) Methods for planning organic syntheses including linear vs convergent synthesis, retrosynthetic analysis using strategic disconnections and synthons, and protecting functional groups. 4) Stereochemistry including enantiomers, chirality, and methods for resolving racemic mixtures like diastereomeric salt formation and chiral chromatography.
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Tema 1.9 Session3
- 1. Mòdul MD2301 - Formació general; 564497 – Química orgànica i inorgànica MASTER ON DRUGS, COSMETICS AND FOOD QUALITY Dr. Antonio Delgado Universitat de Barcelona October 2009
- 2. 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.
- 3. Hückel’s rule : (4n+2) electrons delocalized (conjugated) in a cyclic system Electrophilic aromatic substitution
- 6. Stability of aromatic systems
- 10. Electrophilic aromatic substitution Halogenation
- 11. Electrophilic aromatic substitution Nitration
- 12. Electrophilic aromatic substitution Sulfonation
- 13. Electrophilic aromatic substitution Alkylation
- 16. Electrophilic aromatic substitution on benzene derivatives
- 25. Planning an organic synthesis Construction of the carbon skeleton Linear vs convergent synthesis Linear synthesis Convergent synthesis
- 26. 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
- 27. Equivalence between synthons and reagents
- 28. Functional group transformation Reduction of carbonyl derivatives
- 29. Functional group protection: protecting groups in peptide synthesis: Reactivity control
- 30. Protecting groups in peptide synthesis Directionality in peptide bond formation
- 31. Stereochemical control Enantiomers and chirality
- 32. Enantiomers can show different biological activity
- 33. Resolution of racemic mixtures Chiral chromatography
- 34. Chemical resolution (diastereomeric salt formation)
- 35. An example of diastereomeric salt formation
- 36. Resolution of racemic mixtures Diastereomeric salt formation in “high throughput format”
- 37. Resolution of racemic mixtures Chiral chromatography