CSO201

O i Ch i t F d t l d A li tiOrganic Chemistry: Fundamentals and Applications

J. N. Moorthy (moorthy@) and R. Gurunath (gurunath@)

Organic Chemistry: Fundamentals and ApplicationsBasic Organic Chemistry Concepts: introduction to organic molecules and functionalgroups, understanding organic reactions, stereochemistry and carbon-carbon bond formingreactions in organic synthesis. (8 Lectures)

Drugssome examples including love drugs and molecules of death. (2 Lectures)C f f ( )Chemistry of odours, dyes and flavors (3 Lectures)

Photochemistry: simple concepts and applications (semiconductor photochemistry, solar-energy conversion by photovoltaic cells, photocatalysis, etc.); supramolecular

h h i (4 L )photochemistry. (4 Lectures)

Organic Materials: polymers (biodegradable polymers, conducting polymers, etc.), smartmaterials, OLEDs, intelligent gels, dyes, etc. (4 Lectures)

Green Chemistry - introduction, principles, sustainability, atom economy, some greeninitiatives, management of resources and its effect on health and environment. (6 Lectures)

C t l i d bi t l t i i h i t ti l ti it d hi l th iCatalysis and biocatalysts in organic chemistry. enantioselectivity and chiral synthesis,organocatalysis. (6 Lectures)

Enzymes as drug targets and their inhibitors as model inhibitors (4 Lectures)

Solid phase synthesis and strategies for futuristic designs in organic chemistry. (4 Lectures)

Molecular Structures: SterochemistryA Recapp

Stereochemistry

Conformational Analysis

The case of n-butane

Conformational Analysis

Summary of Steric Strain

Cycloalkanes1964

1980’sUnsuccessful so far!

Cyclohexane Ring Inversion

Stereoisomerism: ChiralityMolecules that lack ‘’ plane and ‘i’ center exhibit optical activity!

Chiral Center or Stereocenter!

Configurational IsomerismConformational Isomerism

Atrop isomers: restricted bond rotation!

Enantiomers: mirror images that are nonsuperimposable.

Some important drugs are chiral! Use of D/L, d/l and +/-

L

Enantiomeric Excess, ee

Diastereomers: stereoisomers that are not related by mirror symmetry.

Molecules with 2 Chiral Centers:All substituents different or only one common to both stereocenters

2‐Amino‐3‐Hydroxybutanoic acid

Diastereomers

Properties depend on ‘Shapes’ and ‘Functional Groups’

Molecules display a variety of interactions depending on the functional groups:

Soaps: Mechanism of Dirt Removal Material Transport across Lipid Bilayer

van der Waals Hydrogen bonding Dipole-dipole interactions Electrostatic (ion…ion)

Protein Structures are controlled by these intermolecular interactions, and areresponsible for the structures that they assume and functions they carry out!

Substitutions Eliminations Additions

Reaction Types

Rearrangements Oxidations Reductions

Most reactions occur by two major reaction types: Homolysis and Heterolysis(Pericylic reactions with no intermediates)

Typical SN1 Reaction

Can we worry about CarbocationReactivity???

Typical SN2 Reaction

A Contrast between SN1 and SN2 Reactions

S S 2 R ti ith M B (RX) th S b t tSome SN2 Reactions with MeBr (RX) as the Substrate

Nucleophilic Substitution Reactions in Biological Systems

Nucleophilic Substitution Reactions in the Synthesis of Drugs

TuberculosisTuberculosis

Antidepressant

Halogenation of Alcohols:

Examples of Mitsunobu Reactionp