Organic Chemistry I MU BPH_C_301_T




Organic Chemistry I

No. Details Hours
1 Structure
1.1 Nomenclature of mono/polyfunctional compounds (trivial and IUPAC) (Heterocycles to be 4
excluded).
1.2 Hybridization states of C, O and N. 1
1.3 Atomic orbitals, Molecular orbitals of sp3 (ethane), sp2 (ethene), and sp (acetylene) and C 2
attached to heteroatoms with lone pairs.
HOMO and LUMO of ethene and the C=O group.
1.4 Basic concepts of electronegativity, hydrogen bonding, inductive effect, dipole moment, log 2
P with examples of monofunctional compounds.
1.5 Concept of aromaticity: Huckel’s rule, identification of aromatic, non-aromatic and anti- 2
aromatic systems based on planarity, conjugation and Huckel’s rule.
1.6 Resonance in aliphatic and aromatic systems: Rules of resonance and stability of the 2
resonance structures.
Tautomerism of keto-enol and imine-enamine systems.
Hyperconjugation.
1.7 Stereochemistry: 6
Concept of configuration and chirality, axes of symmetry, plane of symmetry, center of
symmetry.
Representation of molecules using projection formulae – Fischer, Wedge, Sawhorse and
Newmann.
Geometric Isomerism: Methods of determination of configuration of geometric isomers.
Optical isomerism: Enantiomers and diastereomers.
Nomenclature of stereoisomers including E and Z, D and L and R and S designations.
Conformations of ethane, butane, cyclohexane with their energy profile diagrams.
Conformational analysis of mono- and di-substituted cyclohexanes.
Types of strains: Angle strain (Baeyer Strain), transannular strain (Prelog Strain), torsional
strain (Pitzer strain).
2 Ionization, acidity, basicity and pKa (excluding heterocyclic compounds). 6
3 Geometry, stability and properties of the following reactive intermediates: carbocations, 6
carbanions, carbenes and carbon radicals.
Electrophiles and nucleophiles (including charged and neutral species).
Concept of leaving groups, alkyl shifts and migratory aptitude.
4 Equilibria, rates and mechanisms. 7
5 Mechanism of SN1, SN2, E1 and E2 reactions. 4
Factors affecting substitution and elimination reactions.
Comparison of substitution and elimination reactions.
6 Reactivity of the following functional groups: 4
Alkenes, alkynes, alcohols, phenols, alkyl halides, ethers, aldehydes, ketones, carboxylic

 

acid and derivatives, amines.
(Molecular orbital diagrams for nucleophilic addition to carbonyl group and electrophilic
addition to alkene).
7 Influence of the physicochemical properties of the above mentioned functional groups on 2
the following aspects: receptor binding, formulation and degradation.
TOTAL 48




Books:

  1. Organic Chemistry, Jonathan Clayden, Nick Greeves, and Stuart Warren, Oxford University Press.
  2. Organic Chemistry, Stanley H. Pine, James B. Hendrickson, Donald J. Cram, and George S. Hammond, McGraw-Hill Book Co.
  3. Organic Chemistry, John E McMurry, Brooks/Cole Cengage Learning.
  4. Textbook of Organic Chemistry, P. S. Kalsi, MacMillan India Limited.
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