Course Description:
A comprehensive survey of organic chemistry with emphasis on important synthetic reactions and Stereochemistry, Conformational analysis, Configurations and Chirality, Symmetry elements, Determination of absolute and relative configurations, Stereochemistry of enzyme process, Reaction mechanisms, synthetically useful reactions.
COURSE OUTLINES:
1. Stereochemistry
1.1. Introduction,
1.2. Constitutional Isomerism: Chain isomerism, Positional isomerism, Functional isomerism, Metemerism, Tautomerism,
1.3. Stereo Isomerism,
1.3.1. Conformational isomerism
1.3.2. Configurational isomerism
1.3.2.1. Geometrical Isomerism
1.3.2.2. Optical Isomerism: Enantiomer, Diastereomers.
1.4. Fischer Projection.
1.5. Chirality
1.5.1. Chiral molecules
1.5.2. Stereogenic center
1.5.3. Tetrahedral stereocenter
1.5.4. Chirality arising from stereocenters other than carbon
1.5.5. Chiral molecules with two stereogenic centre
1.5.6. Achiral molecules with two stereogenic centre
1.5.7. Chirality without a stereocenter.
2. Conformations
2.1. Conformer
2.2. Conformations of alkanes
2.3 Conformations of n-butane
2.4. Newman Projection of Conformational isomers.
3. Symmetry
3.1. Element of symmetry
3.1.1. Plane of symmetry
3.1.2. Centre of symmetry
3.2. Plane polarized light
3.3. Optical activity
3.4. Walden inversion.
4. Resolution
4.1. Introduction
4.2. Mechanical separation
4.3. Enzyme Process
4.4. Salt formation
4.4.1. Separation of acid
4.4.2. Separation of base.
5. Relative and Absolute configuration
5.1. Relative configuration
5.2. Absolute configuration
5.3. R-S Notational system: The Cahn-Ingold-Prelog system
5.3.1. Sequence rule.
6. Reaction Mechanism
6.1. Introduction
6.2. Exergonic reaction
6.3. Endergonic reaction
6.4. Transition state
6.5. Reactive intermediate: Carbon ion, Carbonium, Free radical, Carbene, Benzyne, Nitrene.
7. Types of Organic Reaction
7.1. Substitution reaction: Free radical, Ionic mechanism, SN1 & SN2 mechanism
7.2. Addition reaction: Electrophilic & Nucleophilic
7.3. Elimination reaction: α and β elimination
7.4. Rearrangement reaction: Intermolecular and intramolecular rearrangement
7.5. Pericyclic reaction: Electrocyclic reaction, Cyclo additions, Sigmatropic Rearrangement.
8. Applied reactions with synthetic importance
8.1. Bischler-Napieralski Synthesis and their mechanism
8.2. Darzen Condensation their mechanism and applications
8.3. Dieckmann condensation and their mechanism
8.3.1. Extension of Dieckmann condensation
8.4. Acyloin condensation:reaction mechanism of normal and cyclic acyloin
8.5. Stork enamine reaction, mechanism and their applications and synthesis
8.6. Michael reaction, mechanism and their applications
8.7. Mannich reaction their mechanism and synthetic application
8.8. Fischer-Indole Synthesis: Robinson Mechanism
8.9. Synthesis of Tryptamine
8.10. Synthesis of Carbazole
8.11. Synthesis of Papaverine
8.12. Synthesis of Atropine
8.13. Synthesis of Cocaine
8.14. Synthesis of Tricarballylic acid
8.15. Synthesis of Aconitic acid
8.16. Synthesis of Dimedone
8.17. Synthesis of Camphoric acid.
Mode of delivery:
Lecture, Discussion, Demonstration and Seminar on selected topics.
Mode of Assessment:
Assignment, Quiz, Test, Seminar and Final examination
Reference material
1. Text book “Organic Chemistry” fourth edition, Francis A. Carey, McGraw Hill Higher Education.
2. “Key Notes in Organic Chemistry” Andrew F. Parsons, Blackwell Publishing Company, Oxford, UK.
- Teacher: Tewodros Birhanu